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Volumn 46, Issue 12, 2007, Pages 2086-2089

Copper-catalyzed cross-coupling reaction of Grignard reagents with primary-alkyl halides: Remarkable effect of 1-phenylpropyne

Author keywords

Alkynes; Copper; Cross coupling; Grignard reagents

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COPPER; HALOGEN COMPOUNDS;

EID: 34250863375     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603451     Document Type: Article
Times cited : (191)

References (42)
  • 1
    • 34250887174 scopus 로고
    • Ed, L. A. Paquette, Wiley, New York
    • B. H. Lipshutz, S. Sengupta, Organic Reactions, Vol. 41 (Ed.: L. A. Paquette), Wiley, New York, 1992, p. 149.
    • (1992) Organic Reactions , vol.41 , pp. 149
    • Lipshutz, B.H.1    Sengupta, S.2
  • 2
    • 0000571094 scopus 로고    scopus 로고
    • For recent reviews on transition-metal-catalyzed cross-coupling reactions using alkyl halides, see: a
    • For recent reviews on transition-metal-catalyzed cross-coupling reactions using alkyl halides, see: a) D. J. Cárdenas, Angew. Chem. 1999, 111, 3201;
    • (1999) Angew. Chem , vol.111 , pp. 3201
    • Cárdenas, D.J.1
  • 3
  • 10
  • 13
    • 0037165715 scopus 로고    scopus 로고
    • For transition-metal-catalyzed cross-coupling reactions using alkyl chlorides, see a
    • For transition-metal-catalyzed cross-coupling reactions using alkyl chlorides, see a) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222;
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 4222
    • Terao, J.1    Watanabe, H.2    Ikumi, A.3    Kuniyasu, H.4    Kambe, N.5
  • 15
    • 85007271082 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 1945;
    • (2002) Chem. Int. Ed , vol.41 , pp. 1945
    • Angew1
  • 17
  • 21
    • 0001080590 scopus 로고    scopus 로고
    • 3 react with alkyl chlorides and fluorides, see E. C. Ashby, J. J. Lin, J. Org. Chem. 1977, 42, 2805.
    • 3 react with alkyl chlorides and fluorides, see E. C. Ashby, J. J. Lin, J. Org. Chem. 1977, 42, 2805.
  • 22
    • 34250844655 scopus 로고    scopus 로고
    • In this reaction, 0.09 mmol of 1-phenylpropyne was recovered and a trace amount of PhCH=C(Me)nBu (< 0.01 mmol) was formed, probably from a Cu-catalyzed carbomagnezation of 1-phenylpropyne with nBuMgCl.
    • In this reaction, 0.09 mmol of 1-phenylpropyne was recovered and a trace amount of PhCH=C(Me)nBu (< 0.01 mmol) was formed, probably from a Cu-catalyzed carbomagnezation of 1-phenylpropyne with nBuMgCl.
  • 23
    • 0030964143 scopus 로고    scopus 로고
    • Two examples of Cu-catalyzed cross-coupling reactions using sec-alkyl mesylates have been reported, see D. H. Burns, J. D. Miller, H. K. Chan, M. O. Delaney, J. Am. Chem. Soc. 1997, 119, 2125.
    • Two examples of Cu-catalyzed cross-coupling reactions using sec-alkyl mesylates have been reported, see D. H. Burns, J. D. Miller, H. K. Chan, M. O. Delaney, J. Am. Chem. Soc. 1997, 119, 2125.
  • 24
    • 34250801220 scopus 로고    scopus 로고
    • -1, respectively), thus indicating that the reaction of alkyl fluorides is not disfavored energetically.
    • -1, respectively), thus indicating that the reaction of alkyl fluorides is not disfavored energetically.
  • 25
    • 34250846100 scopus 로고    scopus 로고
    • A theoretical study led to a proposed cyclic transition state with an RX-Li interaction, which facilitates cleavage of the R-X bond in the rate-determining step: E. Nakamura, S. Mori, K. Morokuma, J. Am. Chem. Soc. 2000, 122, 7294.
    • A theoretical study led to a proposed cyclic transition state with an RX-Li interaction, which facilitates cleavage of the R-X bond in the rate-determining step: E. Nakamura, S. Mori, K. Morokuma, J. Am. Chem. Soc. 2000, 122, 7294.
  • 28
    • 34250898828 scopus 로고    scopus 로고
    • -1 (at 25°C) for the isomerization of the 5-hexenyl radical to the cyclopentylmethyl radical has been reported, see A. Citterio, F. Minisci, J. Am. Chem. Soc. 1974, 96, 6355.
    • -1 (at 25°C) for the isomerization of the 5-hexenyl radical to the cyclopentylmethyl radical has been reported, see A. Citterio, F. Minisci, J. Am. Chem. Soc. 1974, 96, 6355.
  • 29
    • 0001304781 scopus 로고    scopus 로고
    • -1 (at 25°C) for the isomerization of the cyclopropylmethyl radical to the butenyl radical has been reported, see B. Maillard, D. Forrest, U. K. Ingold, J. Am. Chem. Soc. 1976, 98, 7024.
    • -1 (at 25°C) for the isomerization of the cyclopropylmethyl radical to the butenyl radical has been reported, see B. Maillard, D. Forrest, U. K. Ingold, J. Am. Chem. Soc. 1976, 98, 7024.
  • 36
    • 0001573925 scopus 로고    scopus 로고
    • 2 on reaction with alkyl Grignard reagents, see M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205.
    • 2 on reaction with alkyl Grignard reagents, see M. Tamura, J. K. Kochi, J. Organomet. Chem. 1972, 42, 205.
  • 37
    • 34250808091 scopus 로고    scopus 로고
    • For thermal stabilities of alkylcopper(I) complexes, see A. Miyashita, T. Yamamoto, A. Yamamoto, Bull. Chem. Soc. Jpn. 1977, 50, 1109, and references therein.
    • For thermal stabilities of alkylcopper(I) complexes, see A. Miyashita, T. Yamamoto, A. Yamamoto, Bull. Chem. Soc. Jpn. 1977, 50, 1109, and references therein.
  • 38
    • 0001656392 scopus 로고    scopus 로고
    • For alkynecopper(I) complexes, see P. Schulte, U. Behrens, J. Organomet. Chem. 1998, 563, 235, and references therein.
    • For alkynecopper(I) complexes, see P. Schulte, U. Behrens, J. Organomet. Chem. 1998, 563, 235, and references therein.
  • 42
    • 0034251074 scopus 로고    scopus 로고
    • For bis(alkyne)copper(I) complexes, see G. Gröger, U. Behrens, F. Olbrich, Organometallics 2000, 19, 3354.
    • For bis(alkyne)copper(I) complexes, see G. Gröger, U. Behrens, F. Olbrich, Organometallics 2000, 19, 3354.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.