References
1a
Jones TR.
Webber SE.
Varney MD.
Reddy MR.
Lewis KK.
Kathardekar V.
Mazdiyasni H.
Deal J.
Nguyen D.
Welsh KM.
Webber S.
Johnson A.
Matthews DA.
Smith WW.
Janson CA.
Bacquet RJ.
Howland EF.
Booth CLJ.
Ward RW.
Herrmann SM.
White J.
Bartlett CA.
Morse CA.
J.
Med. Chem.
1997,
40:
677
1b
Neamati N.
Mazumder A.
Zhao H.
Sunder S.
Burke Terrence R.
Schultz RJ.
Pommier Y.
Antimicrob.
Agents Chemother.
1997,
41:
385
1c
Caron G.
Gaillard P.
Carrupt PA.
Testa B.
Helv. Chim. Acta
1997,
80:
449
1d
Prasit P.
Wang Z.
Brideau C.
Chan C.-C.
Charleson S.
Cromlish W.
Ethier D.
Evans JF.
Ford-Hutchinson AW.
Gauthier JY.
Gordon R.
Guay J.
Gresser M.
Kargman S.
Kennedy B.
Leblanc Y.
Léger S.
Mancini J.
O’Neill GP.
Ouellet M.
Percival MD.
Perrier H.
Riendeau D.
Rodger I.
Tagari P.
Thérien M.
Vickers P.
Wong E.
Xu L.-J.
Young R.-N.
Zamboni R.
Bioorg.
Med. Chem. Lett.
1999,
9:
1773
1e
Dinsmore CJ.
Williams TM.
O’Neill TJ.
Liu D.
Rands E.
Culberson JC.
Lobell RB.
Koblan KS.
Kohl NE.
Gibbs JB.
Oliff AI.
Graham SL.
Hartman GD.
Bioorg.
Med. Chem. Lett.
1999,
9:
3301
1f
Seydel JK.
Burger H.
Saxena AK.
Coleman MD.
Smith SN.
Perris AD.
Quant. Struct.-Act. Rel.
1999,
18:
43
1g
Sun Z.-Y.
Botros E.
Su A.-D.
Kim Y.
Wang E.
Baturay NZ.
Kwon C.-H.
J. Med. Chem.
2000,
43:
4160
2a Fumio H, and Mitsuru K. inventors; JP
Patent 61271271.
; Chem. Abstr. 1986, 106, 61271271
2b Keiichi S, Toru O, and Aki S. inventors; JP
Patent 04120050.
; Chem. Abstr. 1992, 117, 150703
2c Toshiaki T, and Takeshi Y. inventors; JP Patent 2001260544.
; Chem. Abstr., 2001, 135, 264604
3
Schank K. In The
Chemistry of Sulfones and Sulfoxides
Patai S.
Rappoport Z.
Stirling CJM.
Wiley;
New York:
1988.
Chap.
7.
4a
Graybill BM.
J. Org. Chem.
1967,
32:
2931
4b
Ueda M.
Uchiyama K.
Kano T.
Synthesis
1984,
323
4c
Truce WE.
Klinger TC.
Brand WW. In Organic Chemistry of Sulfur
Oae S.
Plenum Press;
New
York:
1977.
4d
Nara SJ.
Harjani JR.
Salunkhe MM.
J. Org. Chem.
2001,
66:
8616
4e
Frost CG.
Hartley JP.
Whittle AJ.
Synlett
2001,
830
4f
Bandgar BP.
Kasture SP.
Synth. Commun.
2001,
31:
1065
5
Gilman H.
Beaver NJ.
Meyers CH.
J. Am. Chem. Soc.
1925,
47:
2047
6
Baarschers WH.
Can.
J. Chem.
1976,
54:
3056
7
Suzuki H.
Abe H.
Tetrahedron Lett.
1995,
36:
6239
8
Baskin JM.
Wang Z.
Org. Lett.
2002,
4:
4423
9 Cacchi, S.; Fabrizi, G.; Goggiamani,
A.; Parisi, L. M. Org. Lett., in press.
For some reviews on the substitution
of aryl C-halogen bonds with aryl C-N bonds, see:
10a
Hartwig JF.
Synlett
1997,
329
10b
Baranano D.
Mann G.
Hartwig JF.
Curr. Org.
Chem.
1997,
1:
287
10c
Hartwig JF.
Acc. Chem. Res.
1998,
31:
852
10d
Wolfe JP.
Wagaw S.
Marcoux J.-F.
Buchwald SL.
Acc.
Chem. Res.
1998,
31:
805
10e
Hartwig JF.
Angew. Chem. Int. Ed.
1998,
37:
2046
10f
Hartwig JF.
Pure Appl. Chem.
1999,
71:
1417
10g
Yang BH.
Buchwal d SL.
J.
Organomet. Chem.
1999,
576:
125
For the substitution of aryl C-halogen
bonds with aryl C-PR2 bonds, see:
11a
Herd O.
Hessler A.
Hingst M.
Tepper M.
Stelzer O.
J.
Organomet. Chem.
1996,
522:
69
11b
Herd O.
Hessler A.
Hingst M.
Machnitzki P.
Tepper M.
Stelzer O.
Cat. Today
1998,
42:
413
11c
Machnitzki P.
Nickel T.
Stelzer O.
Landgrafe C.
Eur. J. Inorg. Chem.
1998,
1029
11d
Kraatz H.-B.
Pletsch A.
Tetrahedron: Asymmetry
2000,
11:
1617
11e
Machnitzki P.
Tepper M.
Wenz K.
Stelzer O.
Herdtweck E.
J. Organomet.
Chem.
2000,
602:
158
11f
Hessler A.
Kottsieper KW.
Schenk S.
Tepper M.
Stelzer O.
Z.
Naturforsch. B
2001,
56:
347
11g
Brauer DJ.
Hingst M.
Kottsieper KW.
Liek C.
Nickel T.
Tepper M.
Stelzer O.
Sheldrick WS.
J.
Organomet. Chem.
2002,
645:
14
For the substitution of aryl C-halogen
bonds with aryl C-PO(OR)2 bonds, see:
12a
Hirao T.
Masunaga T.
Ohshiro Y.
Agawa O.
Synthesis
1981,
56
12b
Xu Y.
Zhang J.
J. Chem. Soc., Chem. Commun.
1986,
1606
12c
Casalnuovo AL.
Calabrese JC.
J.
Am. Chem. Soc.
1990,
112:
4324
12d Ref.
[11c]
For the substitution of aryl C-halogen
bonds with aryl C-SR bonds, see:
13a
Harayama H.
Nagahama T.
Kozera T.
Kimura M.
Fugami K.
Tanaka S.
Tamaru Y.
Bull. Chem.
Soc. Jpn.
1997,
70:
445
13b
Kato K.
Ono M.
Akita H.
Tetrahedron
Lett.
1997,
38:
1805
13c
Shopfer U.
Schlapbach A.
Tetrahedron
2001,
57:
3069
13d
Menger FM.
Azov VA.
J.
Am. Chem. Soc.
2002,
124:
11159
14
Kranenburg M.
van der Burgt YEM.
Kramer PCJ.
van Leeuwen PWNM.
Goubitz K.
Fraanje J.
Organometallics
1995,
14:
3081
For the influence of halide additives
on Pd(0)-catalyzed reactions, see:
15a
Jeffery T.
J.
Chem. Soc., Chem. Commun.
1984,
1287
15b
Scott JW.
Crisp GT.
Stille JK.
J. Am. Chem. Soc.
1984,
106:
4630
15c
Amorese A.
Arcadi A.
Bernocchi E.
Cacchi S.
Cerrini S.
Fedeli W.
Ortar G.
Tetrahedron
1989,
45:
813
15d
Larock RC.
Leung W.-Y.
Stolz-Dunn S.
Tetrahedron Lett.
1989,
30:
6629
15e
Loupy A.
Tchoubar B.
Salt
Effects in Organic and Organometallic Chemistry
VCH:
Weinheim:
1992.
p.254-272
15f
Jeffery T.
Gallang JC.
Tetrahedron Lett.
1994,
35:
4103
15g
Herrmann WH.
Brossmer C.
Öfele K.
Reisinger C.-P.
Priermeier T.
Beller M.
Fisher H.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1844
15h
Cacchi S.
Fabrizi G.
Marinelli F.
Pace P.
Tetrahedron
1996,
52:
10225
15i
Jeffery T.
Tetrahedron
1996,
52:
10113
15j
Goodson FE.
Wallow TI.
Novak BM.
J. Am. Chem. Soc.
1997,
119:
12441
15k
Cook GR.
Shanker PS.
Tetrahedron
Lett.
1998,
39:
4991
15l
Roesch KR.
Larock RC.
Org.
Lett.
1999,
1:
1551
15m
Amatore C.
Jutand A.
Acc. Chem. Res.
2000,
33:
314 ; and the references therein
15n
Wang Z.
Zhang Z.
Lu X.
Organometallics
2000,
19:
775
15o
Arcadi A.
Cacchi S.
Fabrizi G.
Marinelli F.
Pace P.
Eur.
J. Org. Chem.
2000,
4099
15p
Zhang Z.
Lu X.
Xu Z.
Zhang Q.
Han X.
Organometallics
2001,
20:
3724
15q
Larock RC.
Reddy CK.
J.
Org. Chem.
2002,
67:
2027
For the influence of halide additives
on divalent palladium-catalyzed reactions, see:
16a
Bäckvall JE.
Nordberg RE.
J.
Am. Chem. Soc.
1980,
102:
393
16b
Bäckvall JE.
Äkermark B.
Ljunggren SO.
J. Am. Chem. Soc.
1979,
101:
2411
16c
Simone DO.
Kennelly T.
Brungard NL.
Farrauto RJ.
Appl.
Catal.
1991,
70:
87
16d
Francis JW.
Henry PM.
J.
Mol. Catal.
1995,
99:
77
16e
Harrington PJ. In Comprehensive Organometallic Chemistry
II
Vol. 12:
Abel EW.
Stone FGA.
Wilkinson G.
Pergamon;
New York:
1995.
p.797
16f
Harrington PJ. In Comprehensive Organometallic Chemistry
II
Vol. 12:
Abel EW.
Stone FGA.
Wilkinson G.
Pergamon;
New York:
1995.
p.904
16g
Widenhoefer RA.
Buchwald SL.
Organometalllics
1996,
15:
2755
16h
Bäckvall JE. In Metal-Catalyzed Cross-Coupling
Reactions
Diederich F.
Stang PJ.
Wiley-VCH;
Weinheim:
1998.
p.339-385
For other reactions in which electron-rich
and electron-poor substrates require different conditions, see for
example:
17a Ref.
[10d]
17b
Yin J.
Buchwald LS.
Org. Lett.
2000,
2:
1101
17c
Cacchi S.
Fabrizi G.
Goggiamani A.
Zappia G.
Org. Lett.
2001,
3:
2539
17d Rutherford, J. F.;
Rainka, M. P.; Buchwald, S. L. J. Am. Chem.
Soc., article as soon as possible.
18
Typical Procedure
for the Preparation of Unsymmetrical Diaryl Sulfones with Electron-Poor
Aryl Bromides or Triflates (Procedure B) (Table 2, Entry 28): In
a Carousel Tube Reaction (Radley Discovery), to a solution of sodium p-toluenesulfinate (0.075 g, 0.420 mmol)
and p-nitrophenyl bromide (0.0707 g,
0.350 mmol) in 2.0 mL of toluene under argon, Pd2(dba)3 (0.008
g, 0.009 mmol), Xantphos (0.010 g, 0.018 mmol) and Cs2CO3 (0.171
g, 0.525 mmol) were added. The mixture was warmed at 120 °C
under stirring for 5 h. After cooling, the reaction mixture was
diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated
under reduced pressure. The reaction mixture was purified by chromatography
(silica gel, 35 g; n-hexane/ethyl
acetate 80/20 v/v) to give 0.076 g of p-nitrophenyl p-tolyl
sulfone (78% yield): Mp 164-165 °C.
IR (KBr): 2926, 1351, 1157 cm-1. 1H
NMR (CDCl3): δ = 8.31 (d, J = 8.9 Hz, 2
H), 8.10 (d, J = 8.9
Hz, 2 H), 7.84 (d, J = 8.4
Hz, 2 H), 7.34 (d, J = 8.1
Hz, 2 H), 2.41 (s, 3 H). 13C NMR (CDCl3): δ = 150.3,
147.9, 145.5, 137.1, 130.4, 128.9, 128.2, 124.5, 21.7. Anal Calcd
for C13H11O4S: C, 56.31; H, 4.00.
Found: C, 56.23; H, 3.99.
With neutral, electron-rich and
slightly electron-poor aryl bromides or triflates, 1.2 equiv of n-Bu4NCl were added (procedure
A).