Abstract
A literature survey of the uses of tertiary phosphine ligands in a variety of catalytic organic reactions, with 231 references, is presented. In addition to separate discussions on several specific phosphine ligand catalyzed reactions, a brief overview of phosphine ligand design along with basic methods for their preparation and some physical properties are also discussed. Where possible, the relative advantages of alkyl and aryl phosphines in these often industrially important organic reactions are compared.
1 Introduction
2 Ligand Design
3 Ligand Preparation
3.1 Building Blocks
3.2 Methods for Ligand Preparation
4 Tertiary Phosphine Applications in Catalysis
4.1 Hydroformylations and Hydrogenations
4.2 Palladium Catalyzed Arylation Reactions
4.3 Palladium Catalyzed Additions to Allylic Systems
4.4 Reppe Carbonylations
4.5 Ruthenium Catalysts for Metathesis Polymerization
5 Conclusions
Key words
catalysis - hydroformylations - Heck reaction - ligands - carbonylations
References
1 Frohning CD.
Kohlpaintner CW. In Applied Homogeneous Catalysis with Organometallic Compounds
Cornils B.
Herrmann WA.
VCH Publishers;
New York:
1996.
p.74-75
2 3 Brandt P.
Andersson PG.
Synlett
2000,
1092
4 Kamer PCJ.
Reek JNH.
van Leeuwen PWNM.
CHEMTECH
1998,
28(9):
27
5 Trost BM.
Van Vranken DL.
Chem. Rev.
1996,
96:
395
6 Kagan HB.
Dang T.-P.
J. Am. Chem. Soc.
1972,
94:
6429
7a Kagan HB. In Asymmetric Synthesis
Vol. 5:
Morrison JD.
Academic Press;
Orlando:
1985.
Chap. 1.
7b Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
8a Whitesell JK.
Chem. Rev.
1989,
89:
1581
8b Trost Van Vranken DL.
Angew. Chem., Int. Ed. Engl.
1992,
31:
228
9a Inoguchi K.
Sakuraba S.
Achiwa K.
Synlett
1992,
169
9b Morimoto T.
Chiba M.
Achiwa K.
Chem. Pharm. Bull.
1993,
41:
1149
9c RajanBabu TV.
Casalnuovo AL.
J. Am. Chem. Soc.
1996,
118:
6325
9d Carmichael D.
Doucet H.
Brown JM.
Chem. Commun.
1999,
261
9e Sannicolo F.
Benincori T.
Rizzo S.
Gladiali S.
Pulacchini S.
Zotti G.
Synthesis
2001,
2327
10 Braunstein P.
Naud F.
Angew. Chem. Int. Ed.
2001,
40:
680
11 Helmchen G.
Pfaltz A.
Acc. Chem. Res.
2000,
33:
336
12 Deerenberg S.
Pàmies O.
Diéguez M.
Claver C.
Kamer PCJ.
van Leeuwen PWNM.
J. Org. Chem.
2001,
66:
7626
13 Pàmies O.
van Strijdonck GPF.
Diéguez M.
Deerenberg S.
Net G.
Ruiz A.
Claver C.
Kamer PCJ.
van Leeuwen PWNM.
J. Org. Chem.
2001,
66:
8867
14 Gilbertson SR.
Xie D.
Fu Z.
J. Org. Chem.
2001,
66:
7240
15 Benincori T.
Gladiali S.
Rizzo S.
Sannicolò F.
J. Org. Chem.
2001,
66:
5940
16 Sugama H.
Saito H.
Danjo H.
Imamoto T.
Synthesis
2001,
2348
17 Fache F.
Schulz E.
Tommasino ML.
Lemaire M.
Chem. Rev.
2000,
100:
2159
18a Oosterom GE.
Reek JNH.
Kamer PCJ.
van Leeuwen PWNM.
Angew. Chem. Int. Ed.
2001,
40:
1828
18b Astruc D.
Chardac F.
Chem. Rev.
2001,
101:
2991
19 Tsiavaliaris G.
Haubrich S.
Merckle C.
Blümel J.
Synlett
2001,
391
20 Allgeier AM.
Mirkin CA.
Angew. Chem. Int. Ed.
1998,
37:
894
21 Katti KV.
Gali H.
Smith CJ.
Berning DE.
Acc. Chem. Res.
1999,
32:
9
22a Lynn DM.
Grubbas RH.
J. Am. Chem. Soc.
2001,
123:
3187
22b Shaughnessy KH.
Booth RS.
Org. Lett.
2001,
3:
2757
23 De Lue N.
Chem. Innovation
2001,
30(11):
33
24a Reetz MT.
Angew. Chem. Int. Ed.
2001,
40:
284
24b Reetz MT.
Becker MH.
Klein H.-W.
Stockigt D.
Angew. Chem. Int. Ed.
1998,
38:
1758
24c Dahmen S.
Brase S.
Synthesis
2001,
1431
24d Jandeleit B.
Schaefer DJ.
Powers TS.
Turner HW.
Weinberg WH.
Angew. Chem. Int. Ed.
1999,
38:
2492
25 Elsner GM.
Regitz E.
Houben-Weyl, Methoden der organischen Chemie, Organische Phosphor-Verbindungen
Band E1:
Thieme Verlag;
Stuttgart:
1982.
Chap. 3.
p.106-183
26 Maier L.
Kosalopoff GM.
Wiley;
New York:
1972.
Chap. 1.
p.1-287
27 Svara J.
Weferling N. In Ullman Encyclopedia of Chemical Technology
5th Ed., Vol. A19:
Elvers B.
Hawkins S.
Schulz G.
VCH;
Weinheim:
1991.
p.545-572
28a Pietrusiewicz KM.
Zablocka M.
Chem. Rev.
1994,
94:
1375
28b Imamoto TE.
Handbook of Organophosphorus Chemistry
Engel R.
Marcel Dekker;
New York:
1992.
Chap. 1.
28c Kagan HB.
Sasaki MF.
Chemistry of Organophosphorus Compounds
Vol. 1:
Hartley R.
Wiley & Sons;
New York:
1990.
Chap. 3.
28d Valentine D.
Asymmetric Synthesis
Vol. 4:
Morrison JD.
Scott JW.
Academic Press;
New York:
1984.
p.263-312
29 Rickelton WA.
Kirk-Othmer Encyclopedia of Chemical Technology
Vol. 18:
Kroschwitz J.
J. Wiley-Interscience;
New York:
1996.
p.656-667
30 Robertson A.
Bradaric C.
Frampton CS.
Mc Nulty J.
Capretta A.
Tetrahedron Lett.
2001,
42:
2609
31a Brown HC. inventors; U.S. 2,584,112.
31b Hoff MC.
Hill P.
J. Org. Chem.
1959,
24:
356
32a Valentine D. inventors; U.S. 4,857,655.
32b Valentine D. inventors; American Cyanamid, U.S. 5,003,093.
33 Calbick CJ, Kuck MJ, and Valentine D. inventors; American Cyanamid, U.S. 5,260,485.
34a Calbick CJ, Kuck MA, and Valentine D. inventors; American Cyanamid, U.S. 5,174,149.
34b Calbick CJ, Kuck MA, and Valentine D. inventors; Cytec Technology Corp., U.S. 5,415,129.
35a Sugiya M, Watanabe T, and Sano N. inventors; Nippon Chemical Industry, U.S. 5,892,120.
35b Sugiya M, Watanabe T, and Sano N. inventors; Nippon Chemical Industry, U.S. 6,025,525.
36 Sugiya M, Watanabe T, and Takeuchi K. inventors; Nippon Chemical Industries, U.S. 5,872,279.
37 Large scale availability of P(cyclo -C6 H11 )2 Cl has been announced.
38 Melvin LS.
Tetrahedron Lett.
1981,
22:
3375
39a Dhawan B.
Redmore D.
J. Org. Chem.
1984,
49:
4018
39b Dhawan B.
Redmore D.
J. Org. Chem.
1986,
51:
179
39c Dhawan B.
Redmore D.
Phosphorus, Sulfur Silicon Relat. Elem.
1989,
42:
177
40a Heinicke J.
Böhle I.
Tzschach A.
J. Organomet. Chem.
1986,
317:
11
40b Heinicke J.
Kadyrov R.
Kellner K.
Nietzschmann E.
Tzschach A.
Phosphorus, Sulfur Silicon Relat. Elem.
1989,
44:
209
41a Paladino J.
Guyard C.
Thurieau C.
Fauchère JL.
Helv. Chim. Acta
1993,
76:
2465
41b Onys’ko PP.
Suvalova EA.
Chudakova TT.
Sinitsa AD.
Heteroat. Chem.
1993,
4:
361
41c Onys’ko PP.
Suvalova EA.
Chudakova TI.
Sinitsa AD.
Russ. J. Gen. Chem.
1994,
64:
554
42a Masson S.
Saint-Clair J.-F.
Saquet M.
Tetrahedron Lett.
1994,
35:
3083
42b Masson S.
Saint-Clair J.-F.
Dore A.
Saquet M.
Bull. Chim. Soc. Fr.
1996,
133:
951
43a Jardine AM.
Vather SM.
Modro TA.
J. Org. Chem.
1988,
53:
3983
43b He Z.
Modro TA.
Synthesis
2000,
565
44a Demay S.
Volant F.
Knochel P.
Angew. Chem. Int. Ed.
2001,
1235
44b Demay S.
Harms K.
Knochel P.
Tetrahedron Lett.
1999,
4981
45 Ohff M.
Holz J.
Quirmbach M.
Börner A.
Synthesis
1998,
1391
46a Nakajima M.
Miyoshi I.
Kanayama K.
Hashimoto S.-I.
Noji M.
Koga K.
J. Org. Chem.
1999,
64:
2264
46b Li X.
Yang J.
Kozlowski MC.
Org. Lett.
2001,
3:
1137
47 Cai D.
Payack JF.
Bender DR.
Hughes DL.
Verhoeven TR.
Reider PJ.
J. Org. Chem.
1994,
59:
7180
48 Ager DJ.
East MB.
Eisenstadt A.
Laneman SA.
Chem. Commun.
1997,
2359
49 Kumobayashi H.
Miura T.
Sayo N.
Saito T.
Zhang X.
Synlett
2001,
1055 ; and references therein
50a Takaya H.
Mashima K.
Koyano K.
Yagi M.
Kumobayashi H.
Taketomi T.
Akutagawa S.
Noyori R.
J. Org. Chem.
1986,
51:
629
50b Miyashita A.
Takaya H.
Souchi T.
Noyori R.
Tetrahedron
1984,
40:
1245
51 Grushin VV.
J. Am. Chem. Soc.
1999,
121:
5831 ; and references therein
52 Shimada T.
Kurushima H.
Cho Y.-H.
Hayashi T.
J. Org. Chem.
2001,
66:
8854
53 Hayashi T.
Hirate S.
Kitayama K.
Tsuji H.
Torii A.
Uozumi Y.
J. Org. Chem.
2001,
66:
1441
54 Hayashi T.
Acc. Chem. Res.
2000,
33:
354
55 Yin J.
Buchwald SL.
J. Am. Chem. Soc.
2000,
122:
12051
56 Ito K.
Kashiwagi R.
Iwasaki K.
Katsuki T.
Synlett
1999,
1563
57 Hillhouse JH. inventors; Cytec Technology Corp., U.S. 5,550,295.
58 Stark GA.
Riermeier TH.
Beller M.
Synth. Commun.
2000,
30:
1703
59 Shelby Q.
Kataoka N.
Mann G.
Hartwig J.
J. Am. Chem. Soc.
2000,
122:
10718
60 Han L.-B.
Tanaka M.
Chem. Commun.
1999,
395 ; and references therein
61 Kazankova MA.
Efimova IV.
Kochetkov AN.
Afanas’ev VV.
Beletskaya IP.
Dixneuf PH.
Synlett
2001,
497
62 Han L.-B.
Zhao C.-Q.
Tanaka M.
J. Org. Chem.
2001,
66:
5929
63 Zhao C.-Q.
Han L.-B.
Goto M.
Tanaka M.
Angew. Chem. Int. Ed.
2001,
40:
1929
64a Han L.-B.
Hua R.
Tanaka M.
Angew. Chem. Int. Ed.
1998,
37:
94
64b Han L.-B.
Tanaka M.
J. Am. Chem. Soc.
1996,
118:
1571
65a Tomori H.
Fox JM.
Buchwald SL.
J. Org. Chem.
2000,
65:
5334
65b Frid M.
Pérez D.
Peat AJ.
Buchwald SL.
J. Am. Chem. Soc.
1999,
121:
9469
66 Tsuruta H.
Imamoto T.
Synthesis
2001,
999
67 Langer F.
Puntener K.
Sturmer R.
Knochel P.
Tetrahedron: Asymmetry
1997,
8:
715
68 Greenfield SJ.
Gilbertson SR.
Synthesis
2001,
2337
69a Gilbertson SR.
Wang X.
J. Org. Chem.
1996,
61:
434
69b Gilbertson SR.
Chen G.
McLoughlin M.
J. Am. Chem. Soc.
1994,
116:
4481
69c Porte AM.
Reibenspies J.
Burgess K.
J. Am. Chem. Soc.
1998,
120:
9180
70 Edwards PG.
Newman PD.
Abdul Malik KM.
Angew. Chem. Int. Ed.
2000,
39:
2922
71a Edwards PG.
Whatton ML.
Haigh R.
Organometallics
2000,
19:
2652
71b Edwards PG.
Newman PD.
Hibbs DE.
Angew. Chem. Int. Ed.
2000,
39:
2722
72 Lambert B.
Desreux JF.
Synthesis
2000,
1668
73a Herrmann WA.
Brossmer C.
Öfele K.
Reisinger C.-P.
Priermeier T.
Beller M.
Fischer H.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1844
73b Brunel JM.
Heumann A.
Buono G.
Angew. Chem. Int. Ed.
2000,
39:
1946
73c Louie J.
Hartwig JF.
Angew. Chem., Int. Ed. Engl.
1996,
35:
2359
74 Ohff M.
Ohff A.
van der Boom ME.
Milstein D.
J. Am. Chem. Soc.
1997,
119:
11687
75 Yin J.
Rainka MP.
Zhang X.-X.
Buchwald SL.
J. Am. Chem. Soc.
2002,
104:
1162
76a Vyskocil S.
Smircina M.
Hanu V.
Poláek M.
Kocovsk P.
J. Org. Chem.
1998,
63:
7738
76b Kocovsk P.
Vyskocil S.
Císarova I.
Sejbal J.
Tilerova I.
Smrcina M.
Lloyd-Jones GC.
Stephen SC.
Butts CP.
Murray M.
Langer V.
J. Am. Chem. Soc.
1999,
121:
7714
77 Stinson SC.
Chem. Eng. News
2001,
78(43):
23
78a Burk MJ.
Feaster JE.
Nugent WA.
Harlow RL.
J. Am. Chem. Soc.
1993,
115:
10125
78b Burk MJ.
Feaster JE.
Harlow RL.
Organometallics
1990,
9:
2653
79 Burk MJ.
Acc. Chem. Res.
2000,
33:
363
80a Jiang Q.
Xiao D.
Zhang Z.
Cao P.
Zhang X.
Angew. Chem. Int. Ed.
1999,
38:
516
80b Hamada Y.
Seto N.
Ohmori H.
Hatano K.
Tetrahedron Lett.
1996,
37:
7565
80c Berens U. inventors; Chirotech Technology Ltd. U.S. 5,936,109.
80d Holz J.
Quirmbach M.
Schmidt U.
Heller D.
Stürmer R.
Börner A.
J. Org. Chem.
1998,
63:
8031
80e Brunel JM.
Legrand O.
Reymond S.
Buono G.
J. Am. Chem. Soc.
1999,
121:
5807
80f Marinetti A.
Jus S.
Labrue F.
Lemarchand A.
Genêt J.-P.
Ricard L.
Synthesis
2001,
2095
80g Vedejs E.
Daugulis O.
J. Am. Chem. Soc.
1999,
121:
5813
80h Landis CR.
Jin W.
Owen JS.
Clark TP.
Angew. Chem. Int. Ed.
2001,
40:
3432
80i Constantieux T.
Brunel J.-M.
Labande A.
Buono G.
Synlett
1998,
49
80j Berens U.
Burk MJ.
Gerlach A.
Hems W.
Angew. Chem. Int. Ed.
2000,
39:
1981
80k Brenchley G.
Fedouloff M.
Merifield E.
Wills M.
Tetrahedron: Asymmetry
1996,
7:
2809
80l Breeden S.
Cole-Hamilton DJ.
Foster DF.
Schwarz GJ.
Wills M.
Angew. Chem. Int. Ed.
2000,
39:
4106
80m Stranne R.
Vasse JL.
Moburg C.
Org. Lett.
2001,
3:
2525
80n Reetz MT.
Waldvogel SR.
Goddard R.
Heterocycles
2000,
52:
935
80o Baccolini G.
Boga C.
Buscaroli RA.
Synthesis
2001,
1938
80p Fujie N.
Matsui M.
Achiwa K.
Chem. Pharm. Bull.
1999,
47:
436
81 Fries G.
Wolf J.
Pfeiffer M.
Stalke D.
Werner H.
Angew. Chem. Int. Ed.
2000,
39:
564
82 Schumann M.
Trevitt M.
Redd A.
Gouverneur V.
Angew. Chem. Int. Ed.
2000,
39:
2491
83 Knowles WS.
Sabacky MJ.
Vineyard BD.
J. Am. Chem. Soc.
1995,
97:
2567
84 Zon G.
Mislow K.
Fortschr. Chem. Forsch.
1971,
19:
61
85a Juge S.
Stephan M.
Merdes R.
Genet JP.
Halut-Desportes S.
J. Chem. Soc., Chem. Commun.
1993,
531
85b Juge S.
Stephan M.
Lafitte JA.
Genet JP.
Tetrahedron Lett.
1990,
31:
6357
85c Juge S.
Genet JP.
Tetrahedron Lett.
1989,
30:
2783
86 Corey EJ.
Chen Z.
Tanoury GJ.
J. Am. Chem. Soc.
1993,
115:
11000
87 Vedejs E.
Donde Y.
J. Am. Chem. Soc.
1997,
119:
9293
88 Muci AR.
Campos KR.
Evans DA.
J. Am. Chem. Soc.
1995,
117:
9075
89 Beak P.
Anderson DR.
Curtis MD.
Laumer JM.
Pippel DJ.
Weisenburger GA.
Acc. Chem. Res.
2000,
33:
715
90 Yamanoi Y.
Imamoto T.
J. Org. Chem.
1999,
64:
2988
91a Imamoto T.
Watanabe J.
Wada Y.
Masuda H.
Yamada H.
Tsuruta H.
Matsukawa S.
Yamaguchi Y.
J. Am. Chem. Soc.
1998,
120:
1635
91b Ohashi A.
Imamoto T.
Org. Lett.
2001,
3:
373
92a Wolfe B.
Livinghouse T.
J. Am. Chem. Soc.
1998,
120:
5116
92b Wolfe B.
Livinghouse T.
J. Org. Chem.
2001,
66:
1514
93 Heath H.
Wolfe B.
Livinghouse T.
Bae SK.
Synthesis
2001,
2341
94a Imamoto T.
Matsuo M.
Nonomura T.
Kishikawa K.
Yanagawa M.
Heteroat. Chem.
1993,
4:
475
94b Imamoto T.
Oshiki T.
Onozawa T.
Matsuo M.
Hikosaka T.
Yanagawa M.
Heteroat. Chem.
1992,
3:
563
95a Graf C.-D.
Malan C.
Knochel P.
Angew. Chem. Int. Ed.
1998,
37:
3014
95b Graf C.-D.
Malan C.
Harms K.
Knochel P.
J. Org. Chem.
1999,
64:
5581
96 Mislow K.
Siegel J.
J. Am. Chem. Soc.
1984,
106:
3319
97 Bei X.
Turner HW.
Weinberg WH.
Guram AS.
Petersen JL.
J. Org. Chem.
1999,
64:
6797
98 Ohmura T.
Yamamoto Y.
Miyaura N.
J. Am. Chem. Soc.
2000,
122:
4990
t -butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly.
99a Littke AF.
Fu GC.
J. Org. Chem.
1999,
64:
10
99b Littke AF.
Fu G.
J. Am. Chem. Soc.
2001,
123:
6989
99c Shaughnessy KH.
Kim P.
Hartwig JF.
J. Am. Chem. Soc.
1999,
121:
2123
99d Littke AF.
Dai C.
Fu GC.
J. Am. Chem. Soc.
2000,
122:
4020
99e Littke AF.
Fu GC.
Angew. Chem. Int. Ed.
1998,
37:
3387
99f Monteith M. inventors; WO 98 16486. Suzuki reaction:
; Chem. Abstr. 1998 , 128 , 294592,
99g Cornils B.
Proc. Res. Dev.
1998,
2:
121
99h Littke AF.
Fu GC.
Angew. Chem. Int. Ed.
1999,
38:
2411
99i Hundertmark T.
Littke AF.
Buchwald SL.
Fu GC.
Org. Lett.
2000,
2:
1729
99j Mann G.
Incarvito C.
Rheingold AL.
Hartwig JF.
J. Am. Chem. Soc.
1999,
121:
3224
99k Hartwig JF.
Polym. Preprints (Am. Chem Soc., Div Polym. Chem.)
2000,
41:
420
99l Hartwig JF.
Goodson FE.
Louie J.
Hauck S.
Polym. Mater. Sci. Eng.
1999,
80:
41
99m Lin SL, Zhou W, and Matcham GW. inventors; Celgro US 6,107,521. Amination:
2000; Chem. Abstr. 2000 , 133 , 179296
99n Nishiyama M.
Yamamoto T.
Koie Y.
Tetrahedron Lett.
1998,
39:
617
99o Yamamoto T.
Nishiyama M.
Koie Y.
Tetrahedron Lett.
1998,
39:
2367
99p Yamamoto T.
Nishiyama M.
Koie Y.
Toso Kenkyu Hokoku
1997,
41:
49
; Chem. Abstr. 1998 , 128 , 180180
99q Hartwig JF.
Kawatsura M.
Hauck SI.
Shaughnessy KH.
Alcazar-Roman LM.
J. Org. Chem.
1999,
64:
5575
99r Watanabe M.
Yamamoto T.
Nishiyama M.
Angew. Chem. Int. Ed.
2000,
39:
2501
99s Goodson FE.
Hauck SI.
Hartwig JF.
J. Am. Chem. Soc.
1999,
121:
7527
99t Braig T.
Muller DC.
Gross M.
Meerholz K.
Nuyken O.
Macromol. Rapid Commun.
2000,
21:
583
99u Dai C.
Fu GC.
J. Am. Chem. Soc.
2001,
123:
2719
99v Kawatsura M.
Hartwig JF.
J. Am. Chem. Soc.
1999,
121:
1473
99w Hartwig JF, Kawatsura M, and Hauck SI. inventors; U.S. 6,100,398. Arylation of ketones malonates etc.:
; Chem. Abstr. 2000 , 131 , 310548
99x Ogawa K.
Radke KR.
Rothstein SD.
Rasmussen SC.
J. Org. Chem.
2000,
66:
9067
100a Goerlich JR.
Schmutzler R.
Phosphorus, Sulfur Silicon Relat. Elem.
1995,
102:
211
100b Stauffer SR.
Beare NA.
Stambuli JP.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
4641
100c Beare NA.
Hartwig JF.
J. Org. Chem.
2002,
67:
541
101a Ehrentraut A.
Zapf A.
Beller M.
Synlett
2000,
1589
101b Zapf A.
Ehrentraut A.
Beller M.
Angew. Chem. Int. Ed.
2000,
39:
4153
101c Stambuli JP.
Kuwano R.
Hartwig JF.
Angew. Chem. Int. Ed.
2002,
41:
4746
102 Simal F.
Demonceau A.
Noels AF.
Angew. Chem. Int. Ed.
1999,
38:
538
103 Wolfe JP.
Singer RA.
Yang BH.
Buchwald SL.
J. Am. Chem. Soc.
1999,
121:
9550
104 Aranyos A.
Old DW.
Kiyomori A.
Wolfe JP.
Sadighi JP.
Buchwald SL.
J. Am. Chem. Soc.
1999,
121:
4369
105 Old DW.
Wolfe JB.
Buchwald SL.
J. Am. Chem. Soc.
1998,
120:
9722
106 Karsch HH.
Z. Naturforsch. B: Chem. Sci.
1983,
38:
1027
107 Hansen SM.
Volland MAO.
Rominger F.
Eisenträger F.
Hofmann P.
Angew. Chem. Int. Ed.
1999,
38:
1273
108 Ohashi A.
Imamoto T.
Org. Lett.
2001,
3:
373
109a Ben-David Y.
Portnoy M.
Milstein D.
J. Am. Chem. Soc.
1989,
11:
8742
109b Ben-David Y.
Portnoy M.
Milstein D.
J. Chem. Soc., Chem. Commun.
1989,
1816
109c Portnoy M.
Milstein D.
Organometallics
1993,
12:
1655
109d Ben-David Y.
Gozin M.
Portnoy M.
Milstein D.
J. Mol. Catal.
1992,
73:
173
109e Blum J.
Berlin O.
Milstein D.
Ben-David Y.
Wassermann BC.
Schutte S.
Schumann H.
Organometallics
2000,
571
110 Kawatsura M.
Hartwig JF.
Organometallics
2002,
20:
1960
111 Shan Z.
Xiong Y.
Zhao D.
Tetrahedron
1999,
55:
3893
112a Nakajima M.
Miyoshi I.
Kanayama K.
Hashimoto SI.
Noji M.
Koga K.
J. Org. Chem.
1999,
64:
2264
112b Li X.
Yang J.
Koslowski MC.
Org. Lett.
2001,
3:
1137
113 Becker JJ.
Gagne MR.
J. Am. Chem. Soc.
2001,
123:
9476
114 Reetz MT.
Mehler G.
Angew. Chem. Int. Ed.
2000,
39:
3889
115 Reetz MT.
Sell T.
Tetrahedron Lett.
2000,
41:
6333
116 Naasz R.
Arnold LA.
Pineschi M.
Keller E.
Feringa BL.
J. Am. Chem. Soc.
1999,
121:
1104
117 Ishihara K.
Kobayashi J.
Inanaga K.
Yamamoto H.
Synlett
2001,
394
118 Yamada YMA.
Shibasaki M.
Tetrahedron Lett.
1998,
39:
5561
119a Singer RA.
Buchwald SL.
Tetrahedron Lett.
1999,
1095
119b Vyskocil M.
Smrcina M.
Kocovsky P.
Tetrahedron Lett.
1998,
39:
9289
120 Vyskocil S.
Jaracz S.
Smrcina M.
ticha M.
Hanu V.
Polàek M.
Kocovsky P.
J. Org. Chem.
1998,
63:
7727
121 Rossini C.
Fanzini L.
Raffaelli A.
Salvadori P.
Synthesis
1992,
503
122 Miyano S.
Nawa M.
Mori A.
Hashimoto H.
Bull. Chem. Soc. Jpn.
1984,
57:
2171
123 Reetz MT.
Haderlein G.
Angermund K.
J. Am. Chem. Soc.
2000,
122:
996
124 Ohkuma T.
Doucet H.
Pham T.
Mikami K.
Korenaga T.
Terada M.
Noyori R.
J. Am. Chem. Soc.
1998,
120:
1086
125 Shaughnessy KH.
Hamann BC.
Hartwig JF.
J. Org. Chem.
1998,
63:
6546
126 Wolfe JP.
Buchwald SL.
J. Org. Chem.
2000,
65:
1144
127 Takaya H.
Ohta T.
Noyori R. In Catalytic Asymmetric Synthesis
Ojima I.
VCH;
New York:
1993.
p.1-39
128 Farraris D.
Young B.
Dudding WJ.
Drury WJ.
Lectka T.
Tetrahedron
1999,
55:
8869
129 Zhang X.
Mashima K.
Koyano K.
Sayo N.
Kumobayashi H.
Akutagawa S.
Takaya S.
J. Chem. Soc., Perkin Trans. 1
1994,
2309
130a Uozumi Y.
Hayashi T.
J. Am. Chem. Soc.
1991,
113:
9987
130b Hayashi T.
Acta Chem. Scand.
1996,
50:
259
131a Torraca KE.
Kuwabe S.-I.
Buchwald SL.
J. Am. Chem. Soc.
2000,
122:
12907
131b Torraca KE.
Huang X.
Parrish CA.
Buchwald SL.
J. Am. Chem. Soc.
2001,
123:
10770
76 also:
132a Ding K.
Wang Y.
Yun H.
Liu J.
Wu Y.
Terada M.
Ohkubo Y.
Mikami K.
Chem.-Eur. J.
1999,
5:
1734
132b Sumi K.
Ikariya T.
Noyori R.
Can. J. Chem.
2000,
78:
697
133 Chieffi A.
Kamikawa K.
Åhman J.
Fox JM.
Buchwald SL.
Org. Lett.
2001,
3:
1897
134 Hamada T.
Chieffi A.
Åhman J.
Buchwald SL.
J. Am. Chem. Soc.
2002,
124:
1261
135 Reetz MT.
Gosberg A.
Goddard R.
Kyang SH.
Chem. Commun.
1998,
2077
136 Hamann B.
Hartwig J.
J. Am. Chem. Soc.
1998,
120:
7369
137a Butler IR.
Cullen WR.
Mann BE.
Nurse CR.
J. Organomet. Chem.
1985,
280:
C47
137b Sielcken OE. inventors; DSM and duPont, EP 0,662,467.
137c Kiss G.
Chem. Rev.
2001,
101:
3435
137d Burk MJ.
Harper GP.
Lee JR.
Kalberg C.
Tetrahedron Lett.
1994,
35:
4963
137e Cullen WR.
Kim TJ.
Einstein FWB.
Organometallics
1983,
2:
714
137f Butler IR.
Cullen WR.
Kim TJ.
Rettig SJ.
Organometallics
1985,
4:
972
138 Lautens M.
Fagnou K.
Rovis T.
J. Am. Chem. Soc.
2000,
122:
5650
139a Feuerstein M.
Laurenti D.
Doucet H.
Santelli M.
Synthesis
2001,
2320
139b Feuerstein M.
Doucet H.
Santelli M.
J. Org. Chem.
2001,
66:
5923
139c Feuerstein M.
Doucet H.
Santelli M.
Synlett
2001,
1458
139d Laurenti D.
Feuerstein M.
Pépe G.
Doucet H.
Santelli M.
J. Org. Chem.
2001,
66:
1633
140 Tolman CA.
Chem. Rev.
1977,
77:
313
141 McAuliffe CA. In Comphrehensive Coordination Chemistry
Vol. 6:
Wilkinson G.
Gillard RD.
McCleverty JA.
Pergamon;
New York:
1987.
p.989-1066
142 Mosbo JA.
DeSanto JT.
Storhoff BN.
Bock PL.
Bloss RE.
Inorg. Chem.
1980,
19:
3086
143 Basato M.
J. Chem. Soc., Dalton Trans.
1986,
217
144 Fernandez AI.
Lee TY.
Reyes C.
Prock A.
Giering WP.
Haar CM.
Nolan SP.
J. Chem. Soc., Perkin Trans. 2
1999,
2631
145 Maier L. In Organic Phosphorus Compounds
Vol. 1:
Kosolapoff G.
Maier L.
John Wiley and Sons Inc.;
New York:
1972.
p.1-287
146 Bush RC.
Angelici RJ.
Inorg. Chem.
1988,
27:
681
147 Slaugh LH.
Mullineaux RD.
J. Organomet. Chem.
1968,
13:
469
148 Böhm LL. In Applied Homogeneous Catalysis with Organometallic Compounds
Cornils B.
Herrmann WA.
VCH Publishers;
New York:
1996.
p.251-256
149a Arhancet JP, and Slaugh LH. inventors; Shell Oil Company, U.S. 5,304,686.
149b Arhancet JP, and Slaugh LH. inventors; Shell Oil Company, U.S. 5,304,691.
150a MacDougall JK.
Simpson MC.
Green MJ.
Cole-Hamilton DJ.
J. Chem. Soc., Dalton Trans.
1996,
1161
150b Reetz MT.
Waldvogel SR.
Goddard R.
Heterocycles
2000,
58:
935
151 Fukuoka A.
Kosugi W.
Morishita F.
Hirano M.
McCaffrey L.
Henderson W.
Komiya S.
Chem. Commun.
1999,
489
152a Beletskaya IP.
Cheprakov AV.
Chem. Rev.
2000,
100:
3009
152b de Meijere A.
Meyer FE.
Angew. Chem., Int. Ed. Engl.
1994,
33:
2379
152c Link JT.
Overman LE.
CHEMTECH
1998,
28(8):
19
152d Amatore C.
Jutand A.
Acc. Chem. Res.
2000,
33:
314
152e Beller M.
Riermeier TH.
Stark G.
Transition Metal Organic Synthesis
Vol. 1:
Beller M.
Bolm C.
Wiley-VCH Verlag GmbH;
Weinheim Germany:
1998.
p.208
152f Cabri W.
Candiani I.
Acc. Chem. Res.
1995,
28:
2
152g Heck RF.
Org. React.
1982,
27:
345
153a Miyaura N.
Suzuki A.
Chem. Rev.
1995,
95:
2457
153b Suzuki A.
Pure Appl. Chem.
1994,
66:
213
153c Suzuki A.
J. Organomet. Chem.
1999,
576:
147
153d Buchwald SL.
Fox JM.
Strem Chemiker
2000,
XVIII:
1
154a Stille JK.
Angew. Chem., Int. Ed. Engl.
1986,
25:
508
154b Farina V.
Krishnamurthy V.
The Stille Reaction
Wiley;
New York:
1998.
155a Hartwig JF.
Angew. Chem. Int. Ed.
1998,
37:
2046
155b Theil F.
Angew. Chem. Int. Ed.
1999,
38:
2345
155c Beller M.
Riermeier TH.
Transition Metal Organic Synthesis
Vol. 1:
Beller M.
Bolm C.
Wiley-VCH GmbH;
Weinheim, Germany:
1998.
p.184-194
155d Ref.
[105
156a Bolm C.
Hildebrand JP.
Muñiz K.
Hermanns N.
Angew. Chem. Int. Ed.
2001,
40:
3284
156b Tenaglia A.
Heumann A.
Angew. Chem. Int. Ed.
1999,
38:
2180
156c Loiseleur O.
Hayashi M.
Schmees N.
Pfaltz A.
Synthesis
1997,
1338
i- C4 H9 )3 complex has been reported useful to form 2-cyano-4′-methylbiphenyl a common intermediate for: Losartan potassium® (duPont), Irbesartan® (Sanofi), Valsartin® (Novartis), and Candesartan® (Takeda).
157a Stinson SC.
Chem. Eng. News
1998,
76(3): 49
157b Stinson SC.
Chem. Eng. News
1998,
76(28):
57
157c Monteith MJ. inventors; Zeneca Ltd. WO 9816848. See also:
; Chem. Abstr. 1998 , 128 , 294592
158 Lloyd-Williams P.
Giralt E.
Chem. Soc. Rev.
2001,
30:
145
159 Stinson SC.
Chem. Eng. News
1999,
77(3):
74
160 Aslam M.
Elango V.
Davenport KG.
Synthesis
1989,
869
161 Evans DA.
DeVries KM. In Glycopeptide Antibiotics Drugs and the Pharmaceutical Sciences
Vol. 63:
Nagarajan R.
Marcel Dekker Inc.;
New York:
1994.
p.63-104
162a The sp2 C-X bond dissociation energies decrease in the order C-Cl = 402kJmol-1 , C-Br = 339kJmol-1 ,C-I = 272kJmol-1 at 298
162b Grushin VV.
Alper H.
Chem. Rev.
1994,
94:
1047
163a For the phosphines PPh3-n (c -C6 H11 )n some reported pKa values are: PPh3 , 2.73; PPh2 (c -C6 H11 ), 5.05; PPh(c -C6 H11 )2 , 7.38; P(c -C6 H11 )3 , 9.7
163b Simal F.
Demonceau A.
Noels AF.
Angew. Chem. Int. Ed.
1999,
38:
538
164 Albisson DA.
Bedford RB.
Lawrence SE.
Scully PN.
Chem Commun.
1998,
2095
165 Valentine D.
Tilley JW.
LeMahieu RA.
J. Org. Chem.
1981,
46:
4614
166a Zhang C.
Huang J.
Trudell ML.
Nolan SP.
J. Org. Chem.
1999,
64:
3804
166b Huang J.
Nolan SP.
J. Am. Chem. Soc.
1999,
121:
9889
166c Yang C.
Nolan SP.
Synlett
2001,
1539
166d Lee S.
Beare NA.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
8410
167 Alcazar-Roman LM.
Hartwig JF.
Rheingold AL.
Liable-Sands LM.
Guzei IA.
J. Am. Chem. Soc.
2000,
122:
4618
168 Culkin DA.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
5816
169 Roy AH.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
1232
170a Hartwig JF.
Pure Appl. Chem.
1999,
71:
1417
170b Hartwig JF.
Acc. Chem. Res.
1998,
31:
852
171a See ref.
[24
171b Porte AM.
Reibenspies J.
Burgess K.
J. Am. Chem. Soc.
1998,
120:
9180
171c Watkins K.
Chem. Eng. News
2001,
79(43):
30
172a Stambuli JP.
Stauffer SR.
Shaughnessy KH.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
2677
172b High throughput screening of Heck reactions see ref.
[101c
172c Loeber O.
Kawatsura M.
Hartwig JF.
J. Am. Chem. Soc.
2001,
123:
4366
172d High throughput evaluation for addition of amines to acrylic acid see ref.
[113
172e Reetz MT.
Kühling KM.
Deege A.
Hinrichs H.
Belder D.
Angew. Chem. Int. Ed.
2000,
39:
3891
173 Parrish CA.
Buchwald SL.
J. Org. Chem.
2001,
66:
3820
174 Buchwald SL, Plante OJ, and Seeberger PH. inventors; WO 2001038377.
; Chem. Abstr. 2001 , 134 , 367135
175 Wolfe JP.
Buchwald SL.
Angew. Chem Int. Ed.
1999,
38:
2413
176 Zapf A.
Beller M.
Chem.-Eur. J.
2000,
6:
1830
177 Beller M.
Fischer H.
Herrmann WA.
Öfele K.
Brossmer C.
Angew. Chem. Int. Ed.
1995,
34:
1848
178 Zim D.
Gruber AS.
Ebeling G.
Dupont J.
Monteiro AL.
Org. Lett.
2000,
2:
2881
179 Bumagin NA.
Bykov VV.
Tetrahedron
1997,
53:
14437
180 Ennis DS.
McManus J.
Wood-Kaczmar W.
Richardson J.
Smith GE.
Carstairs A.
Org. Process Res. Dev.
1999,
3:
248
181a Inada K.
Miyaura N.
Tetrahedron
2000,
56:
8657
181b Inada K.
Miyaura N.
Tetrahedron
2000,
56:
8661
182 Hong R.
Hoen R.
Zhang J.
Lin G.-q.
Synlett
2001,
1527
183 Obtaining fast rates in Heck reactions has been reviewed see: ref.
[152a
184 Beller M.
Zapf A.
Synlett
1998,
7:
792
185 Gurtler C.
Buchwald SL.
Chem.-Eur. J.
1999,
5:
3107
186 Reetz MT.
Lohmer G.
Schwickardi R.
Angew. Chem. Int. Ed.
1998,
37:
481
187a Reetz M.
Westermann E.
Angew. Chem. Int. Ed.
2000,
39:
165
187b Reetz MT.
Westermann E.
Lohmer R.
Lohmer G.
Tetrahedron Lett.
1998,
8449
187c Reetz M, Lohmer G, Lohmer R, and Westermann E. inventors; DE 19843012.
; Chem. Abstr. 2000 , 132 , 222334
187d Reetz MT.
Breinbauer R.
Wanninger K.
Tetrahedron Lett.
1996,
37:
4499
188a Fox JM.
Huang X.
Chieffi A.
Buchwald SL.
J. Am. Chem. Soc.
2000,
122:
1360
188b Palucki M.
Buchwald SL.
J. Am. Chem. Soc.
1997,
119:
11108
189 Moradi WA.
Buchwald SL.
J. Am. Chem. Soc.
2000,
123:
7996
190 Satoh T.
Kawamura Y.
Miura M.
Nomura M.
Angew. Chem. Int. Ed. Engl.
1997,
36:
1740
191 Parrish CA.
Buchwald SL.
J. Org. Chem.
2001,
66:
2498
192 Watanabe M.
Nishiyama M.
Koie Y.
Tetrahedron Lett.
1999,
40:
8837
193a Yang BH.
Buchwald SL.
J. Organomet. Chem.
1999,
576:
125
193b Wolfe JP.
Wagaw S.
Marcoux J.-F.
Buchwald SL.
Acc. Chem. Res.
1998,
31:
805
194 Harris MC.
Geis O.
Buchwald SL.
J. Org. Chem.
1999,
64:
6019
195 Harris MC.
Buchwald SL.
J. Org. Chem.
2000,
65:
5327
196 Wolfe JP.
Tomori H.
Sadighi JP.
Yin J.
Buchwald SL.
J. Org. Chem.
2000,
65:
1158
197 Ali MH.
Buchwald SL.
J. Org. Chem.
2001,
66:
2560
198 Lipschutz BH.
Ueda H.
Angew. Chem. Int. Ed.
2000,
39:
4492
199 Lee S.
Hartwig JF.
J. Org. Chem.
2001,
66:
3402
200 Stauffer SR.
Lee S.
Stambuli JP.
Hauck SI.
Hartwig JF.
Org. Lett.
2000,
2:
1423
201 Wagaw S.
Yang BH.
Buchwald SL.
J. Am. Chem. Soc.
1999,
121:
10251
202 Beller M.
Breindl C.
Riermeier TH.
Tillack A.
J. Org. Chem.
2001,
66:
1403
203 Watanabe M.
Yamamoto T.
Nishiyama M.
Angew. Chem Int. Ed.
2000,
39:
2501
204 Zhang X.-X.
Buchwald SL.
J. Org. Chem.
2000,
65:
8027
205 Old DW.
Harris MC.
Buchwald SL.
Org. Lett.
2000,
2:
1403
206 Zhang X.-X.
Sadighi JP.
Mackewitz TW.
Buchwald SL.
J. Am. Chem. Soc.
2000,
122:
7606
207 Kawatsura M.
Hartwig JF.
J. Am. Chem. Soc.
2000,
122:
9546
208 Beller M. In Applied Homogeneous Catalysis with Organometallic Compounds
Cornils B.
Herrmann WA.
VCH;
Weinheim:
1996.
p.148-159
209 Trost BM.
Acc. Chem. Res.
1980,
13:
385
210 Trost BM.
Toste FD.
J. Am. Chem. Soc.
1999,
121:
454
211 Stranne R.
Vasse J.-L.
Moberg C.
Org. Lett.
2001,
3:
2525
212a Ito K.
Kashiwagi R.
Iwasaki K.
Katsuki T.
Synlett
1999,
1563
212b Ito K.
Kashiwagi R.
Hayashi S.
Uchida T.
Katsuki T.
Synlett
2001,
2:
284
P ,N ligands used in Pd catalysts for asymmetric allylations see:
213a Constantiuex T.
Brunel J.
Labande A.
Buono G.
Synlett
1998,
49
213b Denmark SE.
Wynn T.
J. Am. Chem. Soc.
2001,
123:
6199
213c Achiwa I.
Yamazaki A.
Achiwa K.
Synlett
1998,
45
213d Gilbertson SR.
Genov DG.
Rheingold AL.
Org. Lett.
2000,
2:
2885
214a Suykerbyk JCL, Drent E, and Pringle PG. inventors; Shell WO 98/42717.
214b Drent E, Pello DHL, and Hassalaar M. inventors; Shell U.S. 5,436,356.
215a Buchmeiser MR.
Chem. Rev.
2000,
100:
1565
215b Fürstner A.
Angew. Chem. Int. Ed.
2000,
39:
3012
216a Schrock RR.
Murdzek JS.
Bazan GC.
Robbins J.
Di Mare M.
O’Regan M.
J. Am. Chem. Soc.
1990,
112:
3875
216b Oskam JY.
Fox HH.
Yap KB.
McConville DH.
O’Dell B.
Lichtenstein BY.
Schrock RR.
J. Organomet. Chem.
1993,
459:
185
216c Feldman J.
Murdzek JS.
Davis WM.
Schrock RR.
Organometallics
1989,
8:
2260
217 Nguyen ST.
Grubbs RH.
Ziller JW.
J. Am. Chem. Soc.
1993,
115:
9858
218 Trnka TM.
Grubbs RH.
Acc. Chem. Res.
2001,
34:
18
219a Wu Z.
Nguyen ST.
Grubbs RH.
Ziller JW.
J. Am. Chem. Soc.
1995,
117:
5503
219b Dias EL.
Nguyen ST.
Grubbs RH.
J. Am. Chem. Soc.
1997,
119:
3887
219c Aagaard OM.
Meier RJ.
Buda F.
J. Am. Chem. Soc.
1998,
120:
7174
220a Woodson CS, and Grubbs RH. inventors; Advanced Polymer Technologies WO 9729136.
; Chem. Abstr. 1997 , 127 , 206058
220b Woodson CS, and Grubbs RH. inventors; Advanced Polymer Technologies, WO 97200865.
; Chem. Abstr. 1997 , 127 , 81882
221 Demonceau A.
Stumpf AW.
Saive E.
Noels AF.
Macromolecules
1999,
32:
2091
222a Mohr B.
Lynn DM.
Grubbs RH.
Organometallics
1996,
15:
4317
222b Lynn DM.
Mohr B.
Grubbs RH.
J. Am. Chem. Soc.
1998,
120:
1627
223a Mayr M.
Mayr B.
Buchmeiser MR.
Angew. Chem. Int. Ed.
2001,
40:
3839
223b Kingsbury JS.
Harrity JPA.
Bonitatebus PJ.
Hoveyda AH.
J. Am. Chem. Soc.
1999,
121:
791
223c Garber SB.
Kingsbury JS.
Gray BL.
Hoveyda AH.
J. Am. Chem. Soc.
2000,
122:
8168
223d Kingsbury JH.
Garber SB.
Giftos JM.
Gray BL.
Okamoto MM.
Farrer RA.
Fourkas JT.
Hoveyda AH.
Angew. Chem. Int. Ed.
2001,
40:
4251
224a Herrmann WA.
Köcher C.
Angew. Chem. Int. Ed. Engl.
1997,
36:
2163
224b Huang J.
Schanz H.-J.
Stevens ED.
Nolan SP.
Organometallics
1999,
18:
5375
225a Huang J.
Stevens ED.
Nolan SP.
Peterson JL.
J. Am. Chem. Soc.
1999,
121:
2674
225b Scholl M.
Trnka TM.
Morgan JP.
Grubbs RH.
Tetrahedron Lett.
1999,
40:
2247
225c Fürstner A.
Thiel OL.
Ackermann L.
Schanz H.-J.
Nolan SP.
J. Org. Chem.
2000,
65:
2204
226a Scholl M.
Ding S.
Lee CW.
Grubbs RH.
Org. Lett.
1999,
1:
953
226b Chatterjee AK.
Morgan JP.
Scholl M.
Grubbs RH.
J. Am. Chem. Soc.
2000,
122:
3783
227 Bielawski CW.
Grubbs RH.
Angew. Chem. Int. Ed.
2000,
39:
2903
228 Weskamp T.
Schattenmann WC.
Spiegler M.
Herrmann WA.
Angew. Chem. Int. Ed.
1998,
37:
2490
229 Weskamp T.
Kohl FJ.
Hieringer W.
Gleich D.
Herrmann WA.
Angew. Chem. Int. Ed.
1999,
38:
2416
230a Randl S.
Gessler S.
Wakamatsu H.
Blechert S.
Synlett
2001,
430
230b Wakamatsu H.
Blechert S.
Angew. Chem. Int. Ed.
2002,
41:
794
231 Hansen SM.
Volland MAO.
Rominger F.
Eisenträger F.
Hofmann P.
Angew. Chem. Int. Ed.
1999,
38:
1273
