Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(9): 1399-1427
DOI: 10.1055/s-0029-1218748
DOI: 10.1055/s-0029-1218748
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Transition-Metal-Catalyzed Oxidative Heck Reactions
Further Information
Received
5 January 2010
Publication Date:
19 April 2010 (online)
Publication History
Publication Date:
19 April 2010 (online)
Abstract
Oxidative Heck reactions provide a facile and efficient route to carbon-carbon bond formations. This review is divided into two main sections, the first consisting of oxidative Heck reactions of organometallic compounds such as organoboranes, organosilanols and arylstannanes, and the second covering oxidative Heck reactions via C-H activation, a topic which has become an attractive theme in organic synthesis.
1 Introduction
2 Oxidative Heck Reactions of Organometallic Compounds
2.1 With Palladium(II) Catalysts
2.1.1 Ligand-Free Reactions
2.1.1.1 Anaerobic
2.1.1.2 Aerobic
2.1.2 Ligand-Based Reactions
2.1.2.1 Aerobic
2.1.2.2 Anaerobic
2.1.3 Asymmetric Reactions
2.1.3.1 Aerobic
2.1.3.2 Anaerobic
2.1.4 With Polymer-Supported Palladium(II) Catalysts
2.2 With Other Transition-Metal Catalysts
2.3 With Other Organometallic Compounds
3 Oxidative Heck Reactions of C-H Compounds
3.1 Catalytic Reactions
3.1.1 Intermolecular Reactions
3.1.1.1 Anaerobic
3.1.1.2 Aerobic
3.1.2 Intramolecular Reactions
3.1.2.1 Anaerobic
3.1.2.2 Aerobic
4 Conclusions and Outlook
Key words
oxidative Heck coupling - organometallic reagents - oxygen - transition metals - asymmetric catalysis
- 1
Mizoroki T.Mori K.Ozaki A. Bull. Chem. Soc. Jpn. 1971, 44: 581 - 2
Heck RF.Nolley JP. J. Org. Chem. 1972, 37: 2320 - 3
Grips GT. Chem. Soc. Rev. 1998, 27: 427 - 4
Gabri W.Candiani I. Acc. Chem. Res. 1995, 28: 2 - 5
de Meijere A.Meyer FE. Angew. Chem., Int. Ed. Engl. 1994, 33: 2379 -
6a
Whitcombe NJ.Hii KK.Gibson SE. Tetrahedron 2001, 57: 7449 -
6b
Polshettiwar V.Molnar A. Tetrahedron 2007, 63: 6949 -
6c
Karimi B.Enders D. Org. Lett. 2006, 8: 1237 - 7
The
Mizoroki-Heck Reaction
Oestreich M. Wiley & Sons; Chichester: 2009. - 8
Heck RF. J. Am. Chem. Soc. 1969, 91: 6707 - 9
Dieck HA.Heck RF. J. Org. Chem. 1975, 40: 1083 - 10
Yoshida J.Tamao K.Yamamoto H.Kakui T.Uchida T.Kumada M. Organometallics 1982, 1: 542 - 11
Heck RF. J. Am. Chem. Soc. 1968, 90: 5531 - 12
Cho CS.Uemura S. J. Organomet. Chem. 1994, 465: 85 - 13
Cho CS.Itotani K.Uemura S. J. Organomet. Chem. 1993, 443: 253 - 14
Du X.Suguro M.Hirabayashi K.Mori A. Org. Lett. 2001, 3: 3313 - 15
Andappan MMS.Larhed PNM. Mol. Diversity 2003, 7: 97 - 16
Karabelas K.Westerlund C.Hallberg A. J. Org. Chem. 1985, 50: 3896 - 17
Madin A.Overman LE. Tetrahedron Lett. 1992, 33: 4859 - 18
Pan D.Chen A.Su Y.Zhou W.Li S.Jia W.Xiao J.Liu Q.Zhang L.Jiao N. Angew. Chem. Int. Ed. 2008, 47: 4729 - 19
Su Y.Jiao N. Org. Lett. 2009, 11: 2980 - 20
Bernocchi E.Cacchi S.Ciattini PG.Morera E.Ortar G. Tetrahedron Lett. 1992, 33: 3073 - 21
Kang S.-K.Lee H.-W.Jang S.-B.Kim T.-H.Pyun S.-J. J. Org. Chem. 1996, 61: 2604 - 22
Jung YC.Mishra RK.Yoon CH.Jung KW. Org. Lett. 2003, 5: 2231 - 23
Yoon CH.Yoo KSW.Mishra RK.Jung KW. Org. Lett. 2004, 6: 4037 - 24
Kabalka GW.Guchhait SK.Naravane A. Tetrahedron Lett. 2004, 45: 4685 - 25
Kabalka GW.Guchhait SK. Tetrahedron Lett. 2004, 45: 4021 - 26
Yoo KS.Yoon CH.Jung KW. J. Am. Chem. Soc. 2006, 128: 16384 - 27
Andappan MMS.Nilsson P.Larhed M. Chem. Commun. 2004, 218 - 28
Enquist PA.Lindh J.Nilsson P.Larhed M. Green Chem. 2006, 8: 338 - 29
Andappan MMS.Nilsson P.Von Schenck H.Larhed M. J. Org. Chem. 2004, 69: 5212 - 30
Enquist PA.Nilsson P.Sjberg P.Larhed M. J. Org. Chem. 2006, 71: 8779 - 31
Suzuki A. In Modern Arene ChemistryAstruc D. Wiley-VCH; Weinheim: 2002. p.53 - 32
Lindh J.Enquist PA.Pilotti K.Nilsson P.Larhed M. J. Org. Chem. 2007, 72: 7957 -
33a
Karimi B.Zamani A. J. Iran. Chem. Soc. 2008, 5: 1 -
33b
Karimi B.Zamani A.Clark JH. Organometallics 2005, 24: 4695 -
33c
Karimi B.Zamani A.Abedi S.Clark JH. Green Chem. 2009, 11: 109 - 34
O’Neill J.Yoo KS.Jung KW. Tetrahedron Lett. 2008, 49: 7307 - 35
Lindh J.Sävmarker J.Nilsson P.Sjçberg PJR.Larhed M. Chem. Eur. J. 2009, 15: 4630 - 36
Ruan J.Li X.Saidi O.Xiao J. J. Am. Chem. Soc. 2008, 130: 2424 - 37
Delcamp JH.Brucks AP.White MC. J. Am. Chem. Soc. 2008, 130: 11270 - 38
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1999. - 39
Dounay AB.Overman LE. Chem. Rev. 2003, 103: 2945 - 40
Guiry PJ.Kiely D. Curr. Org. Chem. 2004, 8: 781 - 41
Akiyama K.Wakabayashi K.Mikami K. Adv. Synth. Catal. 2005, 347: 1569 - 42
Trost BM.Jiang CH. Synthesis 2006, 369 - 43
Dodd DW.Toews HE.Carneiro F.Jennings MC.Jones ND. Inorg. Chim. Acta 2006, 359: 2850 - 44
Penn L.Shpruhman A.Gelman D. J. Org. Chem. 2007, 72: 3875 -
45a
Ozawa F.Kubo A.Hayashi T. Tetrahedron Lett. 1992, 33: 1485 -
45b
Trabesinger G.Albinati A.Feiken N.Kunz RW.Pregosin PS.Tschoerner M. J. Am. Chem. Soc. 1997, 119: 6315 -
46a
Jutand A.Mosleh A. Organometallics 1995, 14: 1810 -
46b
Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009 -
47a
Strieter ER.Blackmond DG.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 13978 -
47b
Navarro O.Kelly RA.Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194 -
47c
Zhou J.Fu GC. J. Am. Chem. Soc. 2003, 125: 14726 - 48
Amatore C.Jutand A. J. Organomet. Chem. 1999, 576: 254 -
49a
Samsel EG.Norton JR. J. Am. Chem. Soc. 1984, 106: 5505 -
49b
Ashimori A.Overman LE. J. Org. Chem. 1992, 57: 4571 -
49c
Grigg R.Loganathan V.Santhakumar V.Sridharan V.Teasdale A. Tetrahedron Lett. 1991, 32: 687 -
49d
Brown JM.Perez-Torrente JJ.Alcock NW.Clase HJ. Organometallics 1995, 14: 207 -
50a
Fryzuk MD.Bosnich B. J. Am. Chem. Soc. 1977, 99: 6262 -
50b
Brunkan NM.White PS.Gagne MR. Angew. Chem. Int. Ed. 1998, 37: 1579 - 51
Yoo KS.Park CP.Yoon CH.Sakaguchi S.O’Neill J.Jung KW. Org. Lett. 2007, 9: 3933 -
52a
Sakaguchi S.Yoo KS.O’Neill J.Lee JH.Stewart T.Jung KW. Angew. Chem. Int. Ed. 2008, 47: 9326 -
52b
Yoo KS.O’Neill J.Sakaguchi S.Giles R.Lee JH.Jung KW. J. Org. Chem. 2010, 75: 95 - 53
Xiong DC.Zhang LH.Ye XS. Org. Lett. 2009, 11: 1709 - 54
Likhar PR.Roy M.Roy S.Subhas MS.Kantam ML.Sreedhar B. Adv. Synth. Catal. 2008, 350: 1968 -
55a
Lautens M.Roy A.Fukuoka K.Fagnou K.Martín-Matute B. J. Am. Chem. Soc. 2001, 123: 5358 -
55b
Fagnou K.Lautens M. Chem. Rev. 2003, 103: 169 - 56
Lautens M.Mancuso J.Grover H. Synthesis 2004, 12: 2006 - 57
Amengual R.Michelet V.Genêt J.-P. Tetrahedron Lett. 2002, 43: 5905 - 58
Zou G.Wang Z.Zhu J.Tang J. Chem. Commun. 2003, 2438 - 59
Martinez R.Voica F.Genêt J.-P.Darses S. Org. Lett. 2007, 9: 3213 - 60
Faller JW.Chase KJ. Organometallics 1995, 14: 1592 - 61
Ritleng V.Sutter JP.Pfeffer M.Sirlin C. Chem. Commun. 2000, 129 - 62
Ritleng V.Pfeffer M.Sirlin C. Organometallics 2003, 22: 347 - 63
Farrington EJ.Brown JM.Barnard CFJ.Rowsell E. Angew. Chem. Int. Ed. 2002, 41: 169 - 64
Farrington EJ.Barnard CFJ.Rowsell E.Brown JM. Adv. Synth. Catal. 2005, 347: 185 - 65
Hirabayashi K.Nishihara Y.Mori A.Hiyama T. Tetrahedron Lett. 1998, 39: 7893 - 66
Mori A.Danda Y.Fujii T.Hirabayashi K.Osakada K. J. Am. Chem. Soc. 2001, 123: 10774 - 67
Zhou H.Xu YH.Chung W.-J.Loh T.-P. Angew. Chem. Int. Ed. 2009, 48: 5355 - 68
Hirabayashi K.Ando JI.Nishihara Y.Mori A.Hiyama T. Synlett 1999, 99 - 69
Parrish JP.Jung YC.Shin S.Jung KW. J. Org. Chem. 2002, 67: 7127 - 70
Matoba K.Motofusa SI.Cho CS.Ohe K.Uemura S. J. Organomet. Chem. 1999, 574: 3 - 71
Nunn M.Sowerby DB.Wesolek DM. J. Organomet. Chem. 1983, 251: 45 - 72
Moritani I.Fujiwara Y. Tetrahedron Lett. 1967, 1119 - 73
Fujiwara Y.Moritani I.Matsuda M. Tetrahedron 1968, 4819 - 74
Itahara T.Ikeda M.Sakakibara T. J. Chem. Soc., Perkin Trans. 1 1983, 1361 - 75
Itahara T.Kawasaki K.Ouseto F. Synthesis 1984, 236 - 76
Asano R.Moritani I.Fujiwara Y.Teranishi S. J. Chem. Soc., Chem. Commun. 1970, 1293 - 77
Yogo M.Ito C.Furukawa H. Chem. Pharm. Bull. 1991, 39: 328 - 78
Knölker HJ.O’Sullivan N. Tetrahedron Lett. 1994, 35: 1695 - 79
Knölker HJ.O’Sullivan N. Tetrahedron 1994, 50: 10893 - 80
Baran PS.Corey EJ. J. Am. Chem. Soc. 2002, 124: 7904 - 81
Baran PS.Guerrero CA.Corey EJ. J. Am. Chem. Soc. 2003, 125: 5628 - 82
Garg NK.Caspi DD.Stoltz BM. J. Am. Chem. Soc. 2004, 126: 9552 - 83
Garg NK.Caspi DD.Stoltz BM. J. Am. Chem. Soc. 2005, 127: 5970 - 84
Tsuji J.Nagashima H. Tetrahedron 1984, 40: 2699 - 85
Hirota K.Isobe Y.Kitade Y.Maki Y. Synthesis 1987, 495 - 86
Jia C.Lu W.Kitamura T.Fujiwara Y. Org. Lett. 1999, 1: 2097 - 87
Mikami K.Hatano M.Terada M. Chem. Lett. 1999, 28: 55 - 88
Boele MDK.van Strijdonck GPF.de Vries AHM.Kamer PCJ.de Vries JG.van Leeuwen PWNM. J. Am. Chem. Soc. 2002, 124: 1586 - 89
Zaitsev VG.Daugulis O. J. Am. Chem. Soc. 2005, 127: 4156 - 90
Capito E.Brown JM.Ricci A. Chem. Commun. 2005, 1854 - 91
Grimster NP.Gauntlett C.Godfrey CRA.Gaunt MJ. Angew. Chem. Int. Ed. 2005, 44: 3125 - 92
Beck EM.Grimster NP.Hatley R.Gaunt MJ. J. Am. Chem. Soc. 2006, 128: 2528 - 93
Houlden CE.Bailey CD.Ford JG.Gagné MR.Lloyd-Jones GC.Booker-Milburn KI. J. Am. Chem. Soc. 2008, 130: 10066 - 94
Li J.-J.Mei T.-S.Yu J.-Q. Angew. Chem. Int. Ed. 2008, 47: 6452 - 95
Cho SH.Hwang SJ.Chang S. J. Am. Chem. Soc. 2008, 130: 9254 - 96
Rauf W.Thompson AL.Brown JM. Chem. Commun. 2009, 3874 - 97
Cheng D.Gallagher T. Org. Lett. 2009, 11: 2639 - 98
Koubachi J.Raboin SB.Mouaddib A.Guillaumet G. Synthesis 2009, 271 - 99
Fujiwara Y.Moritani I.Matsuda M.Teranishi S. Tetrahedron Lett. 1968, 3863 - 100
Shue RS. J. Chem. Soc., Chem. Commun. 1971, 1510 - 101
Maruyama O.Yoshidomi M.Fujiwara Y.Taniguchi H. Chem. Lett. 1979, 8: 1229 - 102
Miura M.Tsuda T.Satoh T.Nomura M. Chem. Lett. 1997, 26: 1103 - 103
Miura M.Tsuda T.Satoh T.Pivsa-Art S.Nomura M. J. Org. Chem. 1998, 63: 5211 - 104
Yokota T.Tani M.Sakaguchi S.Ishii Y. J. Am. Chem. Soc. 2003, 125: 1476 - 105
Tani M.Sakaguchi S.Ishii Y. J. Org. Chem. 2004, 69: 1221 - 106
Dams M.De Vos DE.Celen S.Jacobs PA. Angew. Chem. Int. Ed. 2003, 42: 3512 - 107
Yamada T.Sakaguchi S.Ishii Y. J. Org. Chem. 2005, 70: 5471 - 108
Wang JR.Yang CT.Liu L.Guo QX. Tetrahedron Lett. 2007, 48: 5449 - 109
Zhang YH.Shi BF.Yu JQ. J. Am. Chem. Soc. 2009, 131: 5072 - 110
Aouf C.Thiery E.Bras JL.Muzart J. Org. Lett. 2009, 11: 4096 - 111
Åkermark B.Oslob JD.Heuschert U. Tetrahedron Lett. 1995, 36: 1325 - 112
Knölker HJ.Reddy KR.Wagner A. Tetrahedron Lett. 1998, 39: 8267 - 113
Beccalli EM.Broggini G. Tetrahedron Lett. 2003, 44: 1919 - 114
Abbiati G.Beccalli EM.Broggini G.Zoni C. J. Org. Chem. 2003, 68: 7625 - 115
Zhang H.Ferreira EM.Stoltz BM. Angew. Chem. Int. Ed. 2004, 43: 6144 - 116
Youn SW.Eom JI. Org. Lett. 2005, 7: 3355 - 117
Kong A.Han X.Lu X. Org. Lett. 2006, 8: 1339 - 118
Schiffner JA.Machotta AB.Oestreich M. Synlett 2008, 2271 - 119
Bowie AL.Trauner D. J. Org. Chem. 2009, 74: 1581 - 120
Hagelin H.Oslob JD.Åkermark B. Chem. Eur. J. 1999, 5: 2413 - 121
Ferreira EM.Stoltz BM. J. Am. Chem. Soc. 2003, 125: 9578 - 122
Garg NK.Caspi DD.Stoltz BM. Synlett 2006, 3081 - 123
Beccalli EM.Borsini E.Broggini G.Rigamonti M.Sottocornola S. Synlett 2008, 1053