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Synthesis 2003(14): 2115-2134
DOI: 10.1055/s-2003-42082
DOI: 10.1055/s-2003-42082
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Cyclisations Involving Attack of Carbo- and Heteronucleophiles on Carbon-Carbon π-Bonds Activated by Organopalladium Complexes
Further Information
Received
10 February 2003
Publication Date:
24 September 2003 (online)
Publication History
Publication Date:
24 September 2003 (online)
Abstract
In the late 1980’s, a new process based on an intramolecular palladium-mediated cyclisation coupled with a carbon-carbon bond forming reaction appeared in the literature. Since the first report, many novel ring systems have been synthesized using this methodology. The aim of this present review article is to summarise a number of synthetic applications of this new process developed over the last fifteen years.
1 Introduction
2 Carbocycles
2.1 Cyclisation Unactivated Olefins
2.2 Cyclisation of Unactivated Alkynes
3 Heterocycles
3.1 Oxygen Heterocycles
3.2 Nitrogen Heterocycles
4 Conclusion
Key words
catalysis - palladium - carbocycles - heterocycles - cyclisation
- 1
Fournet G.Balme G.Goré J. Tetrahedron Lett. 1987, 28: 4533 - 2
Balme G.Monteiro N.Bouyssi D. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E.-I. Wiley and Sons; New York: 2002. p.2245-2265 - 3
Fournet G.Balme G.Goré J. Tetrahedron Lett. 1989, 30: 69 - 4
Fournet G.Balme G.Goré J. Tetrahedron 1990, 46: 7763 - 5
Bouyssi D.Balme G.Fournet G.Monteiro N.Goré J. Tetrahedron Lett. 1991, 32: 1641 - 6
Balme G.Bouyssi D.Faure R.Goré J.Van Hemelryck B. Tetrahedron 1992, 48: 3891 - 7
Balme G.Bouyssi D. Tetrahedron 1994, 50: 403 - 8
Vittoz P.Bouyssi D.Traversa C.Goré J.Balme G. Tetrahedron Lett. 1994, 35: 1871 - 9
Bouyssi D.Coudanne I.Uriot H.Goré J.Balme G. Tetrahedron Lett. 1995, 36: 8019 - 10
Coudanne I.Castro J.Balme G. Synlett 1998, 995 - 11
Bruyère D.Gaignard G.Bouyssi D.Balme G.Lancelin JM. Tetrahedron Lett. 1997, 38: 827 - 12 To be published. For a recent application to the construction of steroid-like structures see:
Bressy C.Bruyère D.Bouyssi D.Balme G. Arkivoc 2002, Part V: 127 - 13
Fournet G.Balme G.Van Hemelryck B.Goré J. Tetrahedron Lett. 1990, 31: 5147 - 14
Fournet G.Balme G.Goré J. Tetrahedron 1991, 47: 6293 - 15
Coudanne I. PhD Dissertation University of Lyon; France: 1997. - 16
Lomberget T.Bouyssi D.Balme G. Synlett 2002, 1439 - 17
Coudanne I.Balme G. Synlett 1998, 998 - 18
Hosokawa T.Murahashi S.-I. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E.-I. Wiley and Sons; New York: 2002. p.2169-2192 - 19
Hosokawa T. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E.-I. Wiley and Sons; New York: 2002. p.2211-2225 - 20
Tsuda T.Ohashi Y.Nagahama N.Sumiya R.Saegusa T. J. Org. Chem. 1988, 53: 2650 - 21
Arcadi A.Burini A.Cacchi S.Delmastro M.Marinelli F.Pietroni BR. J. Org. Chem. 1992, 57: 976 - 22
Bouyssi D.Goré J.Balme G. Tetrahedron Lett. 1992, 33: 2811 - 23
Bouyssi D.Goré J.Balme G.Louis D.Wallach J. Tetrahedron Lett. 1993, 34: 3129 - 24
Rossi R.Bellina F.Biagetti M.Mannina L. Tetrahedron Lett. 1998, 39: 7599 - 25
Wolf LB.Tjen KCMF.Rutjes FPJT.Hiemstra H.Schoemaker HE. Tetrahedron Lett. 1998, 39: 5081 - 26
Wolf LB.Tjen KCMF.ten Brink HT.Blaauw RH.Hiemstra H.Schoemaker HE.Rutjes FPJT. Adv. Synth. Catal. 2002, 344: 70 - 27
Rossi R.Bellina F.Biagetti M.Catanese A.Mannina L. Tetrahedron Lett. 2000, 41: 5281 - 28
Jacobi PA.Liu H. J. Org. Chem. 1999, 64: 1778 - 29
Jacobi PA.Lanz S.Ghosh I.Leung SH.Löwer F.Pippin D. Org. Lett. 2001, 3: 831 - 30
Jacobi PA.Pippin D. Org. Lett. 2001, 3: 827 - 31
Cavicchioli M.Bouyssi D.Goré J.Balme G. Tetrahedron Lett. 1996, 37: 1429 - 32
Cavicchioli M.Decortiat S.Bouyssi D.Goré J.Balme G. Tetrahedron 1996, 52: 11463 - 33
Bouyssi D.Balme G. Synlett 2001, 1191 - 34
Luo F.-T.Schreuder I.Wang R.-T. J. Org. Chem. 1992, 57: 2213 - 35
Shimizu I.Sugiura T.Tsuji J. J. Org. Chem. 1985, 50: 537 - 36
Walkup RD.Guan L.Mosher MD.Kim SW.Kim YS. Synlett 1993, 88 - 37
Walkup RD.Guan L.Kim YS.Kim SW. Tetrahedron Lett. 1995, 36: 3805 - 38
Kang S.-K.Baik T.-G.Kulak AN. Synlett 1999, 324 - 40
Ma S.Gao W. Synlett 2002, 65 - 41
Ma S.Li L. Org. Lett. 2000, 2: 941 - 42
Aurrecoechea JM.Pérez E. Tetrahedron Lett. 2001, 42: 3839 - 43
Arcadi A.Cacchi S.Del Rosario M.Fabrizi G.Marinelli F. J. Org. Chem. 1996, 61: 9280 - 44
Chaplin JH.Flynn BL. Chem. Commun. 2001, 1594 - 45
Arcadi A.Cacchi S.Fabrizi G.Moro L. Eur. J. Org. Chem. 1999, 61: 1137 - 46
Hu Y.Zhang Y.Yang Z.Fathi R. J. Org. Chem. 2002, 67: 2365 - 47
Flynn BL.Hamel E.Yung MK. J. Med. Chem. 2002, 45: 2670 - 48
Monteiro N.Balme G. Synlett 1998, 746 - 49
Cacchi S.Fabrizi G.Moro L. Synlett 1998, 741 - 50
Cacchi S.Fabrizi G.Moro L. Tetrahedron Lett. 1998, 39: 5101 - 51
Monteiro N.Arnold A.Balme G. Synlett 1998, 1111 - 52
Carangio A.McGuigan C.Andrei G.Snoeck R.De Clercq E.Balzarini J. Antiviral Chem. Chemother. 2001, 187 - 53
Arcadi A.Cacchi S.Larock RC.Marinelli F. Tetrahedron Lett. 1993, 34: 2813 - 54
Cacchi S.Fabrizi G.Moro L. J. Org. Chem. 1997, 62: 5327 - 55
Arcadi A.Rossi E. Tetrahedron Lett. 1996, 37: 6811 - 56
Cavicchioli M.Sixdenier E.Derrey A.Bouyssi D.Balme G. Tetrahedron Lett. 1997, 38: 1763 - 57
Bottex M.Cavicchioli M.Hartmann B.Monteiro N.Balme G. J. Org. Chem. 2001, 66: 175 - 58
Garçon S.Vassiliou S.Cavicchioli M.Hartmann B.Monteiro N.Balme G. J. Org. Chem. 2001, 66: 4069 - 59
Inoue Y.Itoh Y.Yen IF.Imaizumi S. J. Mol. Cat. 1990, 60: L1 - 60
Nakamura H.Ohtaka M.Yamamoto Y. Tetrahedron Lett. 2002, 43: 7631 - 61
Luo F.-T.Wang R.-T. Tetrahedron Lett. 1992, 33: 6835 - 62
Jacobi PA.Liu H. Org. Lett. 1999, 1: 341 - 63
Jacobi PA.Liu H. J. Org. Chem. 2000, 65: 7676 - 64
Arcadi A. Synlett 1997, 941 - 65
Bouyssi D.Cavicchioli M.Balme G. Synlett 1997, 944 - 66
Arcadi A.Cacchi S.Marinelli F. Tetrahedron Lett. 1992, 33: 3915 - 67
Cacchi S.Fabrizi G.Pace P. J. Org. Chem. 1998, 63: 1001 - 68
Arcadi A.Cacchi S.Fabrizi G.Marinelli F. Synlett 2000, 394 - 69
Cacchi S.Fabrizi G.Marinelli F.Moro L.Pace P. Synlett 1997, 1363 - 70
Collini MD.Ellingboe JW. Tetrahedron Lett. 1997, 38: 7963 - 71
Saulnier MG.Frennesson DB.Deshpande MS.Vyas DM. Tetrahedron Lett. 1995, 36: 7841 - 72
Arcadi A.Cacchi S.Carnicelli V.Marinelli F. Tetrahedron 1994, 50: 437 - 73
Cacchi S.Fabrizi G.Pace P.Marinelli F. Synlett 1999, 620 - 74
Battistuzzi G.Cacchi S.Fabrizi G.Marinelli F.Parisi LM. Org. Lett. 2002, 4: 2409 - 75
Arcadi A.Cacchi S.Cassetta A.Fabrizi G.Parisi LM. Synlett 2001, 1605 - 76
Dai G.Larock RC. Org. Lett. 2001, 3: 4035 - 77
Dai G.Larock RC. Org. Lett. 2002, 4: 193 - 78
Dai G.Larock RC. J. Org. Chem. 2002, 67: 7042 - 79
Wei L.-M.Lin C.-F.Wu M.-J. Tetrahedron Lett. 2000, 41: 1215 - 80
Arcadi A.Anacardio R.D’Anniballe G.Gentile M. Synlett 1997, 1315 - 81
Palacios F.Aparicio D.Garcia J.Vicario J.Ezpeleta JM. Eur. J. Org. Chem. 2001, 3357 - 82
Palacios F.Aparicio D.de los Santos JM.Vicario J. Tetrahedron 2001, 57: 1961 - 83
Kimura M.Fugami K.Tanaka Y.Tamaru Y. J. Org. Chem. 1992, 57: 6377 - 84
Davies IW.Scopes DIC.Gallagher T. Synlett 1993, 85 - 85
Kimura M.Tanaka Y.Tamaru Y. J. Org. Chem. 1995, 60: 6377 - 86
Tamaru Y.Kimura M. Synlett 1997, 749 - 87
Rutjes FPJT.Tjen KCMF.Wolf LB.Karstens WFJ.Schoemaker HE.Hiemstra H. Org. Lett. 1999, 1: 717 - 88
Ohno H.Toda A.Miwa Y.Taga T.Osawa E.Yamaoka Y.Fujii N.Ibuka T. J. Org. Chem. 1999, 64: 2992 - 89
Dieter RK.Yu H. Org Lett. 2001, 3: 3855-3858 - 90
Karstens WFJ.Klomp D.Rutjes FPJT.Hiemstra H. Tetrahedron 2001, 57: 5123 - 91
Shimizu I.Tsuji J. Chem. Lett. 1984, 233 - 92
Ahmar M.Cazes B.Goré J. Tetrahedron 1987, 43: 3453 - 93
Karstens WFJ.Rutjes FPJT.Hiemstra H. Tetrahedron Lett. 1997, 38: 6275 - 94
Karstens WFJ.Stol M.Rutjes FPJT.Hiemstra H. Synlett 1998, 1126 - 95
Azoulay S.Monteiro N.Balme G. Tetrahedron Lett. 2002, 44: 9311
References
A similar duality (Heck reaction versus cyclisation reaction) depending on the strengh of the nucleophile was also observed in a palladium mediated cyclisation of olefins (see Scheme [8] ).