Catalytic addition of C-H bonds to multiple bonds

Pure and Applied Chemistry

Volumn 69, Issue 3, 1997, Pages 589-594

  Murai, Shinji ^a   Chatani, Naoto ^a   Kakiuchi, Fumitoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000526624     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199769030589     Document Type: Article

References (62)

1. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
2. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
3. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
4. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
5. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
6. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
7. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
8. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
9. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
10. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
11. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
12. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
13. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
14. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
15. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
16. For representative reviews, see: G. W. Parshall, Acc. Chem. Soc., 3, 139 (1970). D. E. Webster, Adv. Organomet. Chem., 15, 147 (1977). S. Komiya, A. Yamamoto and T. Yamamoto, Yuki Gosei Kagaku Kyokaishi, 38, 633 (1980); Chem. Abstr., 93, 203386 (1980). H. Yamazaki and P. Hong, J. Mol. Catal., 21, 133 (1983). R. G. Bergman, Science, 223, 902 (1984). A. E. Shilov, In Activation of Saturated Hydrocarbons by Transition Metal Complexes, D. Reidel, Dordrecht (1984). M. L. H. Green and D. O'Hare Pure Appl. Chem., 57, 1897 (1985). R. H. Crabtree, Chem. Rev., 85, 245 (1985). M. Tanaka, Yuki Gosei Kagaku Kyokaishi, 46, 832 (1988); Chem. Abstr., 110, 113908 (1989). M. Tanaka, CHEMTECH, 19, 59 (1989). W. D. Jones and F. J. Feher, Acc. Chem. Res., 22, 91 (1989). C. L. Hill, Activation and Functionalization of Alkanes, Wiley New York (1989). J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Avtivation, VCH, New York (1990). R. G. Bergman, Adv. Chem. Ser., 230, 211 (1992).
17. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
18. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
19. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
20. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
21. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
22. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
23. For reviews on ortho-melallation, see: J. Dehand and M. Pfeffer, Coord. Chem. Rev., 18, 327 (1976). M. I. Bruce, Angew. Chem., Int. Ed. Engl., 16, 73 (1977). I. Omae, Chem. Rev., 79, 287 (1979). A. D. Ryabov, Synthesis, 233 (1985). G. R. Newkome, W. E. Puckett, V. K. Gupta and G. E. Kiefer, Chem. Rev., 86, 451 (1986). A. D. Ryabov, Chem. Rev., 90, 403 (1990). M. Pfeffer, Pure Appl. Chem., 64, 335 (1992).
24. R. F. Jordan and D. F. Taylor, J. Am. Chem. Soc., 111, 778 (1989). S. Rodewald and R. F. Jordan, J. Am. Chem. Soc., 116, 4491 (1994).
25. R. F. Jordan and D. F. Taylor, J. Am. Chem. Soc., 111, 778 (1989). S. Rodewald and R. F. Jordan, J. Am. Chem. Soc., 116, 4491 (1994).
26. E. J. Moore, W. R. Pretzer, J. T. O'Connell, J. Harris, L. Labounty, L. Chou and S. S. Grimmer, J. Am. Chem. Soc., 114, 5888 (1992).
27. W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986). G. C. Hsu, W. P. Kosar and W. D. Jones, Organometallics, 13, 385 (1994).
28. W. D. Jones and W. P. Kosar, J. Am. Chem. Soc., 108, 5640 (1986). G. C. Hsu, W. P. Kosar and W. D. Jones, Organometallics, 13, 385 (1994).
29. H. M. Colquhoun, J. Holton, D. J. Thompson and M. V. Twigg, New Pathways for Organic Synthesis Chapter 2, Plenum, New York (1984). R. F. Heck, Palladium Reagents in Organic Synthesis Academic London (1985). Y. Fujiwara, T. Jintoku and K. Takaki, CHEMTECH, 20, 636 (1990).
30. H. M. Colquhoun, J. Holton, D. J. Thompson and M. V. Twigg, New Pathways for Organic Synthesis Chapter 2, Plenum, New York (1984). R. F. Heck, Palladium Reagents in Organic Synthesis Academic London (1985). Y. Fujiwara, T. Jintoku and K. Takaki, CHEMTECH, 20, 636 (1990).
31. H. M. Colquhoun, J. Holton, D. J. Thompson and M. V. Twigg, New Pathways for Organic Synthesis Chapter 2, Plenum, New York (1984). R. F. Heck, Palladium Reagents in Organic Synthesis Academic London (1985). Y. Fujiwara, T. Jintoku and K. Takaki, CHEMTECH, 20, 636 (1990).
32. S.-I. Murahashi, T. Naota and H. Taki, J. Chem. Soc., Chem. Commun., 613 (1985). S.-I. Murahashi, T. Naota and K. Yonemura, J. Am. Chem. Soc., 110, 8256 (1988). S.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc., 112, 7820 (1990). S.-I. Murahashi, T. Saito, T. Naota, H. Kumobayashi and S. Akutagawa, Tetrahedron Lett., 32, 5991 (1991).
33. S.-I. Murahashi, T. Naota and H. Taki, J. Chem. Soc., Chem. Commun., 613 (1985). S.-I. Murahashi, T. Naota and K. Yonemura, J. Am. Chem. Soc., 110, 8256 (1988). S.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc., 112, 7820 (1990). S.-I. Murahashi, T. Saito, T. Naota, H. Kumobayashi and S. Akutagawa, Tetrahedron Lett., 32, 5991 (1991).
34. S.-I. Murahashi, T. Naota and H. Taki, J. Chem. Soc., Chem. Commun., 613 (1985). S.-I. Murahashi, T. Naota and K. Yonemura, J. Am. Chem. Soc., 110, 8256 (1988). S.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc., 112, 7820 (1990). S.-I. Murahashi, T. Saito, T. Naota, H. Kumobayashi and S. Akutagawa, Tetrahedron Lett., 32, 5991 (1991).
35. S.-I. Murahashi, T. Naota and H. Taki, J. Chem. Soc., Chem. Commun., 613 (1985). S.-I. Murahashi, T. Naota and K. Yonemura, J. Am. Chem. Soc., 110, 8256 (1988). S.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi and S. Akutagawa, J. Am. Chem. Soc., 112, 7820 (1990). S.-I. Murahashi, T. Saito, T. Naota, H. Kumobayashi and S. Akutagawa, Tetrahedron Lett., 32, 5991 (1991).
36. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
37. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
38. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
39. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
40. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
41. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
42. T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 111, 5954 (1989). S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 32, 2807 (1991). M. Sawamura, H. Hamashima and Y. Ito, J. Am. Chem. Soc., 114, 8295 (1992). Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 116, 3161 (1994). H. Nemoto, Y. Kubota, Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1665 (1994). Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc., 116, 6019 (1994) S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 117, 12436 (1995).
43. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
44. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
45. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
46. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
47. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
48. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
49. K. Sakai, J. Ide, O. Oda and N. Nakamura, Tetrahedron Lett., 1287 (1972). T. Kondo, Y. Tsuji and Y. Watanabe, Tetrahedron Lett., 28, 6229 (1987). T. B. Marder, C. Roe and D. Milstein, Organometallics, 7, 1451 (1988). T. Kondo, M. Akazome, Y. Tsuji and Y. Watanabe, J. Org. Chem., 55, 1286 (1990). Y. Watanabe, T. Mitsudo and T. Kondo, Shokubai, 34, 173 (1992); Chem. Abstr., 117, 191046 (1992). R. W. Barnhart, X. Wang, P. Noheda, S. H. Borgens, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 116, 1821 (1994).
50. H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Chapter 11, Plenum, New York, (1991).
51. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley (1987). Comprehensive Organometallic Chemistry (G. Wilkinson, F. G. A. Stone and E. W. Abel eds.), Pergamon, Oxford (1982). For a latest example, B. M. Trost, D. L. Romeroand F. Rise, J. Am. Chem. Soc., 116, 4268 (1994).
52. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley (1987). Comprehensive Organometallic Chemistry (G. Wilkinson, F. G. A. Stone and E. W. Abel eds.), Pergamon, Oxford (1982). For a latest example, B. M. Trost, D. L. Romeroand F. Rise, J. Am. Chem. Soc., 116, 4268 (1994).
53. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley (1987). Comprehensive Organometallic Chemistry (G. Wilkinson, F. G. A. Stone and E. W. Abel eds.), Pergamon, Oxford (1982). For a latest example, B. M. Trost, D. L. Romeroand F. Rise, J. Am. Chem. Soc., 116, 4268 (1994).
54. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda and N. Chatani, Nature, 366, 529 (1993). F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995).
55. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda and N. Chatani, Nature, 366, 529 (1993). F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995).
56. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda and N. Chatani, Pure Appl. Chem., 66, 1527 (1994).
57. M. F. McGuiggan and L. H. Pignolet, Inorg. Chem., 21, 2523 (1982).
58. F. Kakiuchi, Y. Yamamoto, N. Chalani and S. Murai, Chem. Lett., 681 (1995).
59. F. Kakiuchi, Y. Tanaka, T. Sato, N. Chatani and S. Murai, Chem. Lett., 679 (1995).
60. F. Kakiuchi, M. Yamauchi, N. Chatani and S. Murai, Chem. Lett., 111 (1996).
61. M. Sonoda, F. Kakiuchi, A. Kamatani, N. Chatani and S. Murai, Chem. Lett. 109 (1996).
62. Jones has shown that the slow step in the catalytic formation of indole from 2,6-xylyl isocyanide is not the step of C-H bond cleavage but the last step involving reductive elimination (see ref. 5).