메뉴 건너뛰기




Volumn 15, Issue 18, 1996, Pages 3770-3772

Diverse mechanistic pathways and selectivities in organo-f-element-catalyzed hydroamination. Intermolecular organolanthanide-catalyzed alkyne and alkene hydroamination

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0000715559     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960293y     Document Type: Article
Times cited : (247)

References (45)
  • 9
    • 77956806755 scopus 로고
    • Page, M. I., Ed.; Elsevier: New York
    • (b) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: New York, 1984; pp 1-54.
    • (1984) The Chemistry of Enzyme Action , pp. 1-54
    • Page, M.I.1
  • 11
    • 0022287431 scopus 로고
    • For hydroamination of olefins using alkali metals at high temperatures and pressures, see; (a) Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917-1926. (b) Howk, B. W.; Little, E. L.; Scott, S. L.; Whitman, G. M. J. Am. Chem. Soc. 1954, 76, 1899-1902.
    • (1985) Pure Appl. Chem. , vol.57 , pp. 1917-1926
    • Pez, G.P.1    Galle, J.E.2
  • 12
    • 0000324064 scopus 로고
    • For hydroamination of olefins using alkali metals at high temperatures and pressures, see; (a) Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917-1926. (b) Howk, B. W.; Little, E. L.; Scott, S. L.; Whitman, G. M. J. Am. Chem. Soc. 1954, 76, 1899-1902.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 1899-1902
    • Howk, B.W.1    Little, E.L.2    Scott, S.L.3    Whitman, G.M.4
  • 13
    • 0027740087 scopus 로고
    • For recent examples of hydroamination mediated by early transition metals, see: (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (c) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723. (d) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324. (e) Walsh, P. J.; Baranger, A. M.; Bergman, E. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. This article begins with a review of conventional hydroamination processes for unsaturated carbon-carbon bonds.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11485-11489
    • McGrane, P.L.1    Livinghouse, T.2
  • 14
    • 0000959461 scopus 로고
    • For recent examples of hydroamination mediated by early transition metals, see: (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (c) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723. (d) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324. (e) Walsh, P. J.; Baranger, A. M.; Bergman, E. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. This article begins with a review of conventional hydroamination processes for unsaturated carbon-carbon bonds.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2753-2763
    • Baranger, A.M.1    Walsh, P.J.2    Bergman, R.G.3
  • 15
    • 0000694603 scopus 로고
    • For recent examples of hydroamination mediated by early transition metals, see: (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (c) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723. (d) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324. (e) Walsh, P. J.; Baranger, A. M.; Bergman, E. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. This article begins with a review of conventional hydroamination processes for unsaturated carbon-carbon bonds.
    • (1993) Organometallics , vol.12 , pp. 3705-3723
    • Walsh, P.J.1    Hollander, F.J.2    Bergman, R.G.3
  • 16
    • 33751391914 scopus 로고
    • For recent examples of hydroamination mediated by early transition metals, see: (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (c) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723. (d) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324. (e) Walsh, P. J.; Baranger, A. M.; Bergman, E. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. This article begins with a review of conventional hydroamination processes for unsaturated carbon-carbon bonds.
    • (1992) J. Org. Chem. , vol.57 , pp. 1323-1324
    • McGrane, P.L.1    Livinghouse, T.2
  • 17
    • 0000239830 scopus 로고
    • For recent examples of hydroamination mediated by early transition metals, see: (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (b) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763. (c) Walsh, P. J.; Hollander, F. J.; Bergman, R. G. Organometallics 1993, 12, 3705-3723. (d) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323-1324. (e) Walsh, P. J.; Baranger, A. M.; Bergman, E. G. J. Am. Chem. Soc. 1992, 114, 1708-1719. This article begins with a review of conventional hydroamination processes for unsaturated carbon-carbon bonds.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1708-1719
    • Walsh, P.J.1    Baranger, A.M.2    Bergman, E.G.3
  • 18
    • 0027232637 scopus 로고
    • For recent examples of hydroamination mediated by middle and late transition metals, see: (a) Brunet, J.-J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1993, 34, 3877-3880. (b) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-I. J. Am. Chem. Soc. 1988, 110, 3994-4002 and references therein. These authors begin by summarizing the strengths and weaknesses of platinum metal-catalyzed transformations. (c) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (d) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297-300.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3877-3880
    • Brunet, J.-J.1    Neibecker, D.2    Philippot, K.3
  • 19
    • 33845280828 scopus 로고
    • and references therein
    • For recent examples of hydroamination mediated by middle and late transition metals, see: (a) Brunet, J.-J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1993, 34, 3877-3880. (b) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-I. J. Am. Chem. Soc. 1988, 110, 3994-4002 and references therein. These authors begin by summarizing the strengths and weaknesses of platinum metal-catalyzed transformations. (c) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (d) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297-300.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3994-4002
    • Tamaru, Y.1    Hojo, M.2    Higashimura, H.3    Yoshida, Z.-I.4
  • 20
    • 33845280868 scopus 로고
    • For recent examples of hydroamination mediated by middle and late transition metals, see: (a) Brunet, J.-J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1993, 34, 3877-3880. (b) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-I. J. Am. Chem. Soc. 1988, 110, 3994-4002 and references therein. These authors begin by summarizing the strengths and weaknesses of platinum metal-catalyzed transformations. (c) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (d) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297-300.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6738-6744
    • Casalnuovo, A.L.1    Calabrese, J.C.2    Milstein, D.3
  • 21
    • 0002913891 scopus 로고
    • For recent examples of hydroamination mediated by middle and late transition metals, see: (a) Brunet, J.-J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1993, 34, 3877-3880. (b) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-I. J. Am. Chem. Soc. 1988, 110, 3994-4002 and references therein. These authors begin by summarizing the strengths and weaknesses of platinum metal-catalyzed transformations. (c) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (d) Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297-300.
    • (1987) Heterocycles , vol.25 , pp. 297-300
    • Fukuda, Y.1    Utimoto, K.2    Nozaki, H.3
  • 22
    • 2742575992 scopus 로고
    • Abstracts of Papers Anaheim, CA, American Chemical Society: Washington, DC, 1995; INOR 012
    • Communicated in part: (a) Li, Y.; Marks, T. J. Abstracts of Papers. 209th National Meeting of the American Chemical Society, Anaheim, CA, 1995; American Chemical Society: Washington, DC, 1995; INOR 012. (b) Li, Y.; Marks, T. J. Presented at the 34th National Organic Symposium of the American Chemical Society, Williamsburg, VA, 1995; Abstract 44.
    • (1995) 209th National Meeting of the American Chemical Society
    • Li, Y.1    Marks, T.J.2
  • 23
    • 85033856415 scopus 로고
    • Williamsburg, VA, Abstract 44
    • Communicated in part: (a) Li, Y.; Marks, T. J. Abstracts of Papers. 209th National Meeting of the American Chemical Society, Anaheim, CA, 1995; American Chemical Society: Washington, DC, 1995; INOR 012. (b) Li, Y.; Marks, T. J. Presented at the 34th National Organic Symposium of the American Chemical Society, Williamsburg, VA, 1995; Abstract 44.
    • (1995) 34th National Organic Symposium of the American Chemical Society
    • Li, Y.1    Marks, T.J.2
  • 27
    • 85033861701 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for full synthetic details, characterization of new compounds, and kinetic plots.
  • 30
    • 85033861039 scopus 로고    scopus 로고
    • note
    • +), m l e 185.1600; found, m l e 185.1602.
  • 32
  • 35
    • 85033860105 scopus 로고
    • Jones, N. D., Ed.; Pergamon Press: Oxford, U.K., Chapter 13
    • (b) Fleming, I. In Comprehensive Organic Chemistry; Jones, N. D., Ed.; Pergamon Press: Oxford, U.K., 1979; Chapter 13.
    • (1979) Comprehensive Organic Chemistry
    • Fleming, I.1
  • 41
  • 45


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.