Abstract
Oxidative coupling reactions offer an elegant method to form
a carbon-carbon bond from two carbon-hydrogen
bonds. The ubiquity of carbon-hydrogen bonds in organic
molecules offers the potential to couple simple starting materials
in order to create products of higher complexity in a single step
without the formation of unwanted waste products. This article reviews
catalytic oxidative coupling reactions that proceed without the
formation of intermediate organometallic species bearing carbon-metal
bonds, focusing on key developments and recent publications.
1 Introduction
2 Arenes
2.1 Binaphthols
2.2 Biphenols and Bianilines
2.3 Other Reactions with Arenes
3 Carbonyl and Related Compounds
4 Amines
4.1 Cyanation
4.2 Arylation
4.3 Nitroalkylation
4.4 Coupling with Carbonyl Compounds
5 Amides
6 Ethers
7 Allylic Compounds
8 Hydrocarbons
8.1 Arylation
8.2 Coupling with Carbonyl Compounds
9 Conclusions and Outlook
Key words
oxidative coupling - C-H bond functionalization - cross-coupling - oxidations - catalysis
References 1 Current address: Max Planck Institut
für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Str.
8, 07745 Jena, Germany.
2a C-H Activation , Topics in Current Chemistry
Vol.
292:
Yu J.-Q.
Shi Z.
Springer-Verlag;
Berlin:
2010.
2b Jazzar R.
Hitce J.
Renaudat A.
Sofack-Kreutzer J.
Baudoin O.
Chem.
Eur. J.
2010,
16:
2654
2c Ackermann L.
Vicente R.
Kapdi A.
Angew.
Chem. Int. Ed.
2009,
48:
9792
2d Lyons TW.
Sanford MS.
Chem.
Rev.
2010,
110:
1147
2e Kulkarni AA.
Daugulis O.
Synthesis
2009,
4087
2f Giri R.
Shi B.-F.
Engle KM.
Maugel N.
Yu J.-Q.
Chem.
Soc. Rev.
2009,
38:
3242
2g Kakiuchi F.
Kochi T.
Synthesis
2008,
19:
3013
2h Dick AR.
Sanford MS.
Tetrahedron
2006,
62:
2439
2i Crabtree RH.
J. Chem. Soc., Dalton Trans.
2001,
2437
2j Shilov AE.
Shul’pin GB.
Chem.
Rev.
1997,
97:
2879
3 Anastas P.
Eghbali N.
Chem. Soc. Rev.
2010,
39:
301
4a Scheuermann CJ.
Chem. Asian J.
2010,
5:
436
4b Yoo W.-J.
Li C.-J.
Top. Curr. Chem.
2010,
292:
281
4c Li C.-J.
Acc.
Chem. Res.
2009,
42:
335
5a Podgorscaronek A.
Zupan M.
Iskra J.
Angew. Chem. Int. Ed.
2009,
48:
8424
5b Collet F.
Dodd RH.
Dauban P.
Chem.
Commun.
2009,
5061
6 Brunel JM.
Chem.
Rev.
2005,
105:
857
7a Kozlowski MC.
Morgan BJ.
Linton EC.
Chem. Soc.
Rev.
2009,
38:
3193
7b Takizawa S.
Chem.
Pharm. Bull.
2009,
57:
1179
7c Bringmann G.
Mortimer AJP.
Keller PA.
Gresser MJ.
Garner J.
Breuning M.
Angew.
Chem. Int. Ed.
2005,
44:
5384
7d Chen Y.
Yekta S.
Yudin AK.
Chem.
Rev.
2003,
103:
3155
7e Reddy PP.
Chu C.-Y.
Hwang D.-R.
Wang S.-K.
Uang B.-J.
Coord.
Chem. Rev.
2003,
237:
257
8a von Richter V.
Chem. Ber.
1873,
6:
1249
8b Dianin AP.
Zh. Russ. Fiz-Khim. O-va
1874,
183
9 Brackman W.
Havinga E.
Recl. Trav. Chim. Pays-Bas
1955,
74:
1021
10 Noji M.
Nakajima M.
Koga K.
Tetrahedron
Lett.
1994,
35:
7983
11 Smrčina M.
Poláková J.
Vyskočil S.
Kočovský P.
12a Nakajima M.
Miyoshi I.
Kanayama K.
Hashimoto S.-i.
Noji M.
Koga K.
J.
Org. Chem.
1999,
64:
2264
12b Li X.
Yang J.
Kozlowski MC.
Org.
Lett.
2001,
3:
1137
12c Li X.
Hewgley JB.
Mulrooney CA.
Yang J.
Kozlowski MC.
J. Org. Chem.
2003,
68:
5500
12d Habaue S.
Seko T.
Okamoto Y.
Macromolecules
2003,
36:
2604
12e Kim KH.
Lee D.-W.
Lee Y.-S.
Ko D.-H.
Ha D.-C.
Tetrahedron
2004,
60:
9037
13 Nakajima M.
Kanayama K.
Miyoshi I.
Hashimoto S.-i.
Tetrahedron Lett.
1995,
36:
9519
14 Gao J.
Reibenspies JH.
Martell AE.
Angew.
Chem. Int. Ed.
2003,
42:
6008
15 Temma T.
Habaue S.
Tetrahedron Lett.
2005,
46:
5655
16 Habaue S.
Temma T.
Sugiyama Y.
Yan P.
Tetrahedron Lett.
2007,
48:
8595
17 Grandbois A.
Mayer M.-.
Bédard M.
Collins SK.
Michel T.
Chem.
Eur. J.
2009,
15:
9655
18a Kozlowski MC.
Dugan EC.
DiVirgilio ES.
Maksimenka K.
Bringmann G.
Adv. Synth.
Catal.
2007,
349:
583
18b O’Brien EM.
Morgan BJ.
Kozlowski MC.
Angew. Chem. Int.
Ed.
2008,
47:
6877
18c Morgan BJ.
Dey S.
Johnson SW.
Kozlowski MC.
J.
Am. Chem. Soc.
2009,
131:
9413
19 Tsubaki K.
Org.
Biomol. Chem.
2007,
5:
2179
20 Yan P.
Sugiyama Y.
Takahashi Y.
Kinemuchi H.
Temma T.
Habaue S.
Tetrahedron
2008,
64:
4325
21 Morgan BJ.
Xie X.
Phuan P.-W.
Kozlowski MC.
J. Org. Chem.
2007,
72:
6171
22 Hwang D.-R.
Chen C.-P.
Uang B.-J.
Chem.
Commun.
1999,
1207
23a Hon S.-W.
Li C.-H.
Kuo J.-H.
Barhate NB.
Liu Y.-H.
Wang Y.
Chen C.-T.
Org.
Lett.
2001,
3:
869
23b Chu C.-Y.
Hwang D.-R.
Wang S.-K.
Uang B.-J.
Chem. Commun.
2001,
980
24a Luo Z.
Liu Q.
Gong L.
Cui X.
Mi A.
Jiang Y.
Chem. Commun.
2002,
914
24b Luo Z.
Liu Q.
Gong L.
Cui X.
Mi A.
Jiang Y.
Angew.
Chem. Int. Ed.
2002,
41:
4532
24c Somei H.
Asano Y.
Yoshida T.
Takizawa S.
Yamataka H.
Sasai H.
Tetrahedron Lett.
2004,
45:
1841
24d Guo Q.-X.
Wu Z.-J.
Luo Z.-B.
Liu Q.-Z.
Ye J.-L.
Luo S.-W.
Cun L.-F.
Gong L.-Z.
J.
Am. Chem. Soc.
2007,
129:
13927
24e Takizawa S.
Katayama T.
Kameyama C.
Onitsuka K.
Suzuki T.
Yanagida T.
Kawai T.
Sasai H.
Chem. Commun.
2008,
1810
24f Takizawa S.
Katayama T.
Somei H.
Asano Y.
Yoshida T.
Kameyama C.
Rajesh D.
Onitsuka K.
Suzuki T.
Mikami M.
Yamataka H.
Jayaprakash D.
Sasai H.
Tetrahedron
2008,
64:
3361
25 Takizawa S.
Rajesh D.
Katayama T.
Sasai H.
Synlett
2009,
1667
26 Tada M.
Taniike T.
Kantam LM.
Iwasawa Y.
Chem. Commun.
2004,
2542
27 Egami H.
Katsuki T.
J. Am. Chem. Soc.
2009,
131:
6082
28 Egami H.
Matsumoto K.
Oguma T.
Kunisu T.
Katsuki T.
J.
Am. Chem. Soc.
2010,
132:
13633
29 Irie R.
Masutani K.
Katsuki T.
Synlett
2000,
1433
30 Boldron C.
Aromi G.
Challa G.
Gamez P.
Reedijk J.
Chem. Commun.
2005,
5808
31 Sharma S.
Barooah N.
Baruah JB.
J.
Mol. Catal. A: Chem.
2005,
229:
171
32 Yusa Y.
Kaito I.
Akiyama K.
Mikami K.
Chirality
2010,
22:
224
33a Ashenhurst JA.
Chem. Soc. Rev.
2010,
39:
540
33b McGlacken GP.
Bateman LM.
Chem.
Soc. Rev.
2009,
38:
2447
33c Sarhan AAO.
Bolm C.
Chem.
Soc. Rev.
2009,
38:
2730
34 Li Y.
Jin J.
Qian W.
Bao W.
Org.
Biomol. Chem.
2010,
8:
326
35 Dohi T.
Maruyama A.
Yoshimura M.
Morimoto K.
Tohma H.
Kita Y.
Angew. Chem. Int. Ed.
2005,
44:
6193
36 Guo X.
Yu R.
Li H.
Li Z.
J.
Am. Chem. Soc.
2009,
131:
17387
37 Minisci F.
Fontana F.
Tetrahedron Lett.
1994,
35:
1427
38 Deng G.
Li C.-J.
Org. Lett.
2009,
11:
1171
39 Deng G.
Ueda K.
Yanagisawa S.
Itami K.
Li C.-J.
Chem.
Eur. J.
2009,
15:
333
40 DeMartino MP.
Chen K.
Baran PS.
J.
Am. Chem. Soc.
2008,
130:
11546
41 Leffingwell JC.
Chem.
Commun.
1970,
357
42a Ito Y.
Konoike T.
Saegusa T.
J. Am. Chem. Soc.
1975,
97:
2912
42b Narasaka K.
Okauchi T.
Tanaka K.
Murakami M.
Chem. Lett.
1992,
21:
2099
43a Mukherjee S.
Yang JW.
Hoffmann S.
List B.
Chem. Rev.
2007,
107:
5471
43b Melchiorre P.
Marigo M.
Carlone A.
Bartoli G.
Angew. Chem. Int. Ed.
2008,
47:
6138
44 Kharasch MS.
Sosnovsky G.
Tetrahedron
1958,
3:
97
45 Kozlowski MC.
DiVirgilio ES.
Malolanarasimhan K.
Mulrooney CA.
Tetrahedron:
Asymmetry
2005,
16:
3599
46 Monguchi Y.
Takahashi T.
Iida Y.
Fujiwara Y.
Inagaki Y.
Maegawa T.
Sajiki H.
Synlett
2008,
2291
47 Fan R.
Ye Y.
Li W.
Wang L.
Adv.
Synth. Catal.
2008,
350:
2488
48 Ye Y.
Zheng C.
Fan R.
Org. Lett.
2009,
11:
3156
49 Beeson TD.
Mastracchio A.
Hong J.-B.
Ashton K.
MacMillan DWC.
Science
2007,
316:
582
50a Nicolaou KC.
Reingruber R.
Sarlah D.
Bräse S.
50b Conrad JC.
Kong J.
Laforteza BN.
MacMillan DWC.
J.
Am. Chem. Soc.
2009,
131:
11640
51a Campos KR.
Chem. Soc. Rev.
2007,
36:
1069
51b Li Z.
Bohle DS.
Li C.-J.
Proc.
Natl. Acad. Sci. U.S.A.
2006,
103:
8928
52 Santamaria J.
Herlem D.
Khuong-Huu F.
Tetrahedron
1977,
33:
2389
53 Chiba T.
Takata Y.
J. Org. Chem.
1977,
42:
2973
54 Murata S.
Teramoto K.
Miura M.
Nomura M.
Bull. Chem. Soc. Jpn.
1993,
66:
1297
55 Murahashi S.-I.
Komiya N.
Terai H.
Nakae T.
J. Am. Chem. Soc.
2003,
125:
15312
56 Li Z.
Li C.-J.
J. Am. Chem. Soc.
2005,
127:
6968
57 Liu P.
Zhou C.-Y.
Xiang S.
Che C.-M.
Chem.
Commun.
2010,
46:
2739
58 Ohta M.
Quick MP.
Yamaguchi J.
Wünsch B.
Itami K.
Chem.
Asian J.
2009,
4:
1416
59 Li Z.
Li C.-J.
J. Am. Chem. Soc.
2005,
127:
3672
60 Baslé O.
Li C.-J.
Green Chem.
2007,
9:
1047
61 Zeng T.
Song G.
Moores A.
Li C.-J.
Synlett
2010,
2002
62 Condie AG.
González-Gómez JC.
Stephenson CRJ.
J. Am.
Chem. Soc.
2010,
132:
1464
63 Shu X.-Z.
Yang Y.-F.
Xia X.-F.
Ji K.-G.
Liu X.-Y.
Liang Y.-M.
Org. Biomol. Chem.
2010,
8:
4077
64 Pandey G.
Kumaraswamy G.
Reddy PY.
Tetrahedron
1992,
48:
8295
65 Li Z.
Li C.-J.
Eur. J. Org. Chem.
2005,
3173
66 Richter H.
Mancheño OG.
Eur. J.
Org. Chem.
2010,
4460
67a Catino AJ.
Nichols JM.
Nettles BJ.
Doyle MP.
J. Am. Chem. Soc.
2006,
128:
5648
67b Shen Y.
Tan Z.
Chen D.
Feng X.
Li M.
Guo C.-C.
Zhu C.
Tetrahedron
2009,
65:
158
67c Sureshkumar D.
Sud A.
Klussmann M.
Synlett
2009,
1558
67d Chu L.
Zhang X.
Qing F.-L.
Org. Lett.
2009,
11:
2197
68 Shen Y.
Li M.
Wang S.
Zhan T.
Tan Z.
Guo C.-C.
Chem.
Commun.
2009,
953
69 Sud A.
Sureshkumar D.
Klussmann M.
Chem.
Commun.
2009,
3169
70 Pintér A.
Sud A.
Sureshkumar D.
Klussmann M.
Angew. Chem. Int. Ed.
2010,
49:
5004
71 Ibrahem I.
Samec JSM.
Bäckvall JE.
Córdova A.
Tetrahedron
Lett.
2005,
46:
3965
72 Yoshida J.-i.
Suga S.
Suzuki S.
Kinomura N.
Yamamoto A.
Fujiwara K.
J. Am. Chem. Soc.
1999,
121:
9546
73a Sasamoto N.
Dubs C.
Hamashima Y.
Sodeoka M.
73b Dubs C.
Hamashima Y.
Sasamoto N.
Seidel TM.
Suzuki S.
Hashizume D.
Sodeoka M.
J.
Org. Chem.
2008,
73:
5859
74a Hayashi Y.
Mukaiyama T.
Chem.
Lett.
1987,
16:
1811
74b Xu YC.
Roy C.
Lebeau E.
Tetrahedron
Lett.
1993,
34:
8189
75 Zhang Y.
Li C.-J.
Angew. Chem. Int. Ed.
2006,
45:
1949
76 Zhang Y.
Li C.-J.
J. Am. Chem. Soc.
2006,
128:
4242
77 Yoo W.-J.
Correia CA.
Zhang Y.
Li C.-J.
Synlett
2009,
138
78 Li Z.
Yu R.
Li H.
Angew. Chem.
Int. Ed.
2008,
47:
7497
79a Jensen T.
Fristrup P.
Chem.
Eur. J.
2009,
15:
9632
79b Moiseev II.
Vargaftik MN.
Coord.
Chem. Rev.
2004,
248:
2381
79c Andrus MB.
Lashley JC.
Tetrahedron
2002,
58:
845
79d Eames J.
Watkinson M.
Angew. Chem. Int. Ed.
2001,
40:
3567
80 Cheng D.
Bao W.
Adv. Synth. Catal.
2008,
350:
1263
81 Borduas N.
Powell DA.
J. Org. Chem.
2008,
73:
7822
82 Hanefeld W.
Hunz I.
Arch. Pharm.
1993,
326:
323
83 Damu GLV.
Jon Paul Selvam J.
Venkata Rao C.
Venkateswarlu Y.
Tetrahedron Lett.
2009,
50:
6154
84 Li Y.-Z.
Li B.-J.
Lu X.-Y.
Lin S.
Shi Z.-J.
Angew. Chem.
Int. Ed.
2009,
48:
381
85a Nishino H.
Bull. Chem. Soc. Jpn.
1986,
59:
1733
85b Nishino H.
Kamachi H.
Baba H.
Kurosawa K.
86 Li Z.
Cao L.
Li C.-J.
Angew. Chem.
Int. Ed.
2007,
46:
6505
87 Cheng D.
Bao W.
J. Org. Chem.
2008,
73:
6881
88 Guo C.
Song J.
Luo S.-W.
Gong L.-Z.
Angew.
Chem. Int. Ed.
2010,
49:
5558
89 Correia CA.
Li C.-J.
Tetrahedron Lett.
2010,
51:
1172
90 Benfatti F.
Capdevila MG.
Zoli L.
Benedetto E.
Cozzi PG.
Chem.
Commun.
2009,
5919
91 Ho X.-H.
Mho S.-i.
Kang H.
Jang H.-Y.
Eur. J. Org. Chem.
2010,
4436
92 Zhang Y.
Li C.-J.
Eur. J. Org. Chem.
2007,
4654
