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Volumn , Issue 1, 1996, Pages 1-24

Palladium-catalyzed hydrogenolysis of allylic and propargylic compounds with various hydrides

Author keywords

1 alkene formation; allene formation; allyl as protecting group; formic acid; internal alkyne formation

Indexed keywords

ALKENE DERIVATIVE; POLYENE;

EID: 0030031026     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4175     Document Type: Review
Times cited : (151)

References (166)
  • 1
    • 0003441482 scopus 로고
    • Wiley: Chichester
    • Books and reviews for palladium-catalyzed reactions of allylic compounds: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, p 290. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: Berlin, 1980, p 125. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1985, p 117. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon: Oxford, 1982, Vol. 8, p. 799. Godleski, S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol 4, p 585. Frost, C. G.; Howwarth, J.; William, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
    • (1995) Palladium Reagents and Catalysts , pp. 290
    • Tsuji, J.1
  • 2
    • 0004125888 scopus 로고
    • Springer: Berlin
    • Books and reviews for palladium-catalyzed reactions of allylic compounds: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, p 290. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: Berlin, 1980, p 125. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1985, p 117. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon: Oxford, 1982, Vol. 8, p. 799. Godleski, S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol 4, p 585. Frost, C. G.; Howwarth, J.; William, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
    • (1980) Organic Synthesis with Palladium Compounds , pp. 125
    • Tsuji, J.1
  • 3
    • 0003624033 scopus 로고
    • Academic: London
    • Books and reviews for palladium-catalyzed reactions of allylic compounds: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, p 290. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: Berlin, 1980, p 125. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1985, p 117. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon: Oxford, 1982, Vol. 8, p. 799. Godleski, S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol 4, p 585. Frost, C. G.; Howwarth, J.; William, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
    • (1985) Palladium Reagents in Organic Synthesis , pp. 117
    • Heck, R.F.1
  • 4
    • 84942767100 scopus 로고
    • Wilkinson, G., Ed., Pergamon: Oxford
    • Books and reviews for palladium-catalyzed reactions of allylic compounds: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, p 290. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: Berlin, 1980, p 125. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1985, p 117. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon: Oxford, 1982, Vol. 8, p. 799. Godleski, S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol 4, p 585. Frost, C. G.; Howwarth, J.; William, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 799
    • Trost, B.M.1    Verhoeven, T.R.2
  • 5
    • 0000276556 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford
    • Books and reviews for palladium-catalyzed reactions of allylic compounds: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, p 290. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: Berlin, 1980, p 125. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1985, p 117. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon: Oxford, 1982, Vol. 8, p. 799. Godleski, S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol 4, p 585. Frost, C. G.; Howwarth, J.; William, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 585
    • Godleski, S.1
  • 6
    • 0026722772 scopus 로고
    • Books and reviews for palladium-catalyzed reactions of allylic compounds: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, p 290. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: Berlin, 1980, p 125. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: London, 1985, p 117. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon: Oxford, 1982, Vol. 8, p. 799. Godleski, S. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol 4, p 585. Frost, C. G.; Howwarth, J.; William, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
    • (1992) Tetrahedron Asymmetry , vol.3 , pp. 1089
    • Frost, C.G.1    Howwarth, J.2    William, J.M.J.3
  • 7
    • 0345176035 scopus 로고
    • Hey, H.; Arpe, H. J. Angew. Chem. 1973, 85, 986; Angew. Chem., Int. Ed. Engl. 1973, 12, 928.
    • (1973) Angew. Chem. , vol.85 , pp. 986
    • Hey, H.1    Arpe, H.J.2
  • 8
    • 84981911760 scopus 로고
    • Hey, H.; Arpe, H. J. Angew. Chem. 1973, 85, 986; Angew. Chem., Int. Ed. Engl. 1973, 12, 928.
    • (1973) Angew. Chem., Int. Ed. Engl. , vol.12 , pp. 928
  • 13
    • 0000282382 scopus 로고
    • Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591. Guibe, F.; Xian, H. X.; Balavoine, G. J. Organometal. Chem. 1986, 306, 257 and 267.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3591
    • Guibe, F.1    Saint M'Leux, Y.2
  • 21
    • 0001660243 scopus 로고
    • Keinan, E.; Greenspoon, N. J. Org. Chem. 1983, 48, 3545; 1988, 53, 3723; Isr. J. Chem. 1984, 24, 82.
    • (1988) J. Org. Chem. , vol.53 , pp. 3723
  • 22
    • 0001372768 scopus 로고
    • Keinan, E.; Greenspoon, N. J. Org. Chem. 1983, 48, 3545; 1988, 53, 3723; Isr. J. Chem. 1984, 24, 82.
    • (1984) Isr. J. Chem. , vol.24 , pp. 82
  • 30
    • 9044231789 scopus 로고
    • Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177; Pure Appl. Chem. 1992, 64, 421.
    • (1992) Pure Appl. Chem. , vol.64 , pp. 421
  • 35
    • 0542428095 scopus 로고
    • Use of ammonium formate or triethylammonium formate for the palladium-catalyzed hydrogenolysis of aryl and alkenyl halides has been reported. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491 and 1978, 43, 3985. Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236. Review, Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
    • (1977) J. Org. Chem. , vol.42 , pp. 3491
    • Cortese, N.A.1    Heck, R.F.2
  • 36
    • 33846436723 scopus 로고
    • Use of ammonium formate or triethylammonium formate for the palladium-catalyzed hydrogenolysis of aryl and alkenyl halides has been reported. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491 and 1978, 43, 3985. Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236. Review, Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
    • (1978) J. Org. Chem. , vol.43 , pp. 3985
  • 37
    • 0000860734 scopus 로고
    • Use of ammonium formate or triethylammonium formate for the palladium-catalyzed hydrogenolysis of aryl and alkenyl halides has been reported. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491 and 1978, 43, 3985. Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236. Review, Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
    • (1983) J. Org. Chem. , vol.48 , pp. 4236
    • Cacchi, S.1    Arcadi, A.2
  • 38
    • 85004724143 scopus 로고
    • Use of ammonium formate or triethylammonium formate for the palladium-catalyzed hydrogenolysis of aryl and alkenyl halides has been reported. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491 and 1978, 43, 3985. Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236. Review, Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
    • (1988) Synthesis , pp. 91
    • Ram, S.1    Ehrenkaufer, R.E.2
  • 44
    • 85070844877 scopus 로고
    • Lautens, M.; Delanghe, P. N. M. Angew. Chem. 1994, 106, 2557; Angew. Chem. Int. Ed. Engl. 1994, 33, 2448.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2448
  • 67
    • 0027314220 scopus 로고
    • Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326; Tetrahedron 1993, 49, 5483.
    • (1993) Tetrahedron , vol.49 , pp. 5483
  • 71
    • 0028158805 scopus 로고
    • Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 6090; Tetrahedron 1994, 50, 475.
    • (1994) Tetrahedron , vol.50 , pp. 475
  • 83
    • 0346602829 scopus 로고
    • Reviews, Tsuji, J. Tetrahedron 1986, 42, 4361. Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
    • (1986) Tetrahedron , vol.42 , pp. 4361
    • Tsuji, J.1
  • 84
  • 88
    • 0028091316 scopus 로고
    • Shimizu, I.; Ishii, H. Chem. Lett. 1989, 577; Tetrahedron 1994, 50, 487.
    • (1994) Tetrahedron , vol.50 , pp. 487
  • 92
    • 0026743027 scopus 로고
    • Koch, T.; Hesse, M. Synthesis 1992, 931, 1995, 251. Koch, T.; Ognyanov, V. I.; Hesse, M. Helv. Chim. Acta 1992, 75, 62.
    • (1992) Synthesis , pp. 931
    • Koch, T.1    Hesse, M.2
  • 93
    • 9044228809 scopus 로고
    • Koch, T.; Hesse, M. Synthesis 1992, 931, 1995, 251. Koch, T.; Ognyanov, V. I.; Hesse, M. Helv. Chim. Acta 1992, 75, 62.
    • (1995) Synthesis , pp. 251
  • 103
    • 0345239439 scopus 로고
    • Kotake, H.; Yamamoto, T.; Kinoshita, H. Chem. Lett. 1982, 1331. Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781.
    • (1982) Chem. Lett. , pp. 1331
    • Kotake, H.1    Yamamoto, T.2    Kinoshita, H.3
  • 110
    • 0003145860 scopus 로고
    • Kunz, H.; Waldmann, H. Angew. Chem. 1984, 96, 49; Angew. Chem., Int. Ed. Engl. 1984, 23, 71; J. Chem. Soc. Chem. Commun. 1985, 638. Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751. Ciommer, M.; Kunz, H. Synlett 1991, 593.
    • (1984) Angew. Chem. , vol.96 , pp. 49
    • Kunz, H.1    Waldmann, H.2
  • 111
    • 0004629033 scopus 로고
    • Kunz, H.; Waldmann, H. Angew. Chem. 1984, 96, 49; Angew. Chem., Int. Ed. Engl. 1984, 23, 71; J. Chem. Soc. Chem. Commun. 1985, 638. Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751. Ciommer, M.; Kunz, H. Synlett 1991, 593.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 71
  • 112
    • 9044232901 scopus 로고
    • Kunz, H.; Waldmann, H. Angew. Chem. 1984, 96, 49; Angew. Chem., Int. Ed. Engl. 1984, 23, 71; J. Chem. Soc. Chem. Commun. 1985, 638. Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751. Ciommer, M.; Kunz, H. Synlett 1991, 593.
    • (1985) J. Chem. Soc. Chem. Commun. , pp. 638
  • 113
    • 0000088713 scopus 로고
    • Kunz, H.; Waldmann, H. Angew. Chem. 1984, 96, 49; Angew. Chem., Int. Ed. Engl. 1984, 23, 71; J. Chem. Soc. Chem. Commun. 1985, 638. Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751. Ciommer, M.; Kunz, H. Synlett 1991, 593.
    • (1989) J. Org. Chem. , vol.54 , pp. 751
    • Bochnitschek, S.1    Waldmann, H.2    Kunz, H.3
  • 114
    • 85004880020 scopus 로고
    • Kunz, H.; Waldmann, H. Angew. Chem. 1984, 96, 49; Angew. Chem., Int. Ed. Engl. 1984, 23, 71; J. Chem. Soc. Chem. Commun. 1985, 638. Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751. Ciommer, M.; Kunz, H. Synlett 1991, 593.
    • (1991) Synlett , pp. 593
    • Ciommer, M.1    Kunz, H.2
  • 120
  • 121
    • 84985624920 scopus 로고
    • Kunz, H.; Unverzagt, C. Angew. Chem. 1984, 96, 426; Angew. Chem., Int. Ed. Engl. 1984, 23, 436.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 436
  • 142
  • 143
    • 84980139599 scopus 로고
    • Boss, R.; Schefford, R. Angew. Chem. 1976, 88, 578; Angew. Chem., Int. Ed. Engl. 1976, 15, 558.
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 558
  • 161
    • 0000217818 scopus 로고
    • Colas, Y.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 25, 845; Bull. Soc. Chim. Fr. 1986, 165.
    • (1986) Bull. Soc. Chim. Fr. , pp. 165


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