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Volumn 132, Issue 20, 2010, Pages 6910-6911

Rhodium(III)-catalyzed intermolecular hydroarylation of alkynes

Author keywords

[No Author keywords available]

Indexed keywords

GOOD YIELD; HYDROARYLATION; INTERMOLECULAR REACTIVITY; INTERNAL ALKYNES; METALATIONS; RHODIUM CATALYSTS;

EID: 77952573385     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103080d     Document Type: Article
Times cited : (284)

References (46)
  • 26
    • 0034677867 scopus 로고    scopus 로고
    • Fujiwara reported the first hydroarylation, which was initially thought to proceed through arene metallation. See
    • Fujiwara reported the first hydroarylation, which was initially thought to proceed through arene metallation. See: Jia, C., Piao, D., Oyamada, J., Lu, W., Kitamura, T., and Fujiwara, Y. Science 2000, 287, 1992
    • (2000) Science , vol.287 , pp. 1992
    • Jia, C.1    Piao, D.2    Oyamada, J.3    Lu, W.4    Kitamura, T.5    Fujiwara, Y.6
  • 27
    • 0034596339 scopus 로고    scopus 로고
    • However, futher mechanistic studies have suggested that the reaction proceeds through a Friedel-Crafts-type reaction of a metal-activated alkyne. See: Organometallics 2005, 24, 6440
    • Jia, C., Lu, W., Oyamada, J., Kitamura, T., Matsuda, K., Irie, M., and Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252 However, futher mechanistic studies have suggested that the reaction proceeds through a Friedel-Crafts-type reaction of a metal-activated alkyne. See: Tunge, J. A. and Foresee, L. N. Organometallics 2005, 24, 6440
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7252
    • Jia, C.1    Lu, W.2    Oyamada, J.3    Kitamura, T.4    Matsuda, K.5    Irie, M.6    Fujiwara, Y.7    Tunge, J.A.8    Foresee, L.N.9
  • 34
    • 77952573351 scopus 로고    scopus 로고
    • For a screen of indole protecting groups, see the Supporting Information
    • For a screen of indole protecting groups, see the Supporting Information.
  • 38
    • 77952565354 scopus 로고    scopus 로고
    • Use of the dimethylcarbamoyl protecting group in this case led to poor conversion to product
    • Use of the dimethylcarbamoyl protecting group in this case led to poor conversion to product.
  • 39
    • 77952555338 scopus 로고    scopus 로고
    • Under the standard reaction conditions, terminal and dialkyl alkynes afforded only trace amounts of product
    • Under the standard reaction conditions, terminal and dialkyl alkynes afforded only trace amounts of product.
  • 40
    • 77952559436 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details
  • 41
    • 77952560621 scopus 로고    scopus 로고
    • Under the same reaction conditions, using 1a and PivOD resulted in deuterium incorporation at the alkene position. A control experiment revealed no H/D exchange at the alkene of 3a under the reaction conditions
    • Under the same reaction conditions, using 1a and PivOD resulted in deuterium incorporation at the alkene position. A control experiment revealed no H/D exchange at the alkene of 3a under the reaction conditions.
  • 42
    • 77952560096 scopus 로고    scopus 로고
    • Under the standard reaction conditions in the absence of catalyst, no deuterium loss was observed
    • Under the standard reaction conditions in the absence of catalyst, no deuterium loss was observed.
  • 43
    • 0000663764 scopus 로고
    • For an example of reactivity of a cationic metal with alkynes, see
    • For an example of reactivity of a cationic metal with alkynes, see: Burns, R. M. and Hubbard, J. L. J. Am. Chem. Soc. 1994, 116, 9514
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9514
    • Burns, R.M.1    Hubbard, J.L.2
  • 44
    • 67449127136 scopus 로고    scopus 로고
    • A competition between methoxyindole 1b and nitroindole 1c revealed a preference for the more electron-rich arene (4:1 ratio), which is consistent with C-H bond cleavage via electrophilic activation, as previously demonstrated for related systems. See
    • A competition between methoxyindole 1b and nitroindole 1c revealed a preference for the more electron-rich arene (4:1 ratio), which is consistent with C-H bond cleavage via electrophilic activation, as previously demonstrated for related systems. See: Li, L., Brennessel, W. W., and Jones, W. D. Organometallics 2009, 28, 3492
    • (2009) Organometallics , vol.28 , pp. 3492
    • Li, L.1    Brennessel, W.W.2    Jones, W.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.