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Volumn 133, Issue 7, 2011, Pages 2116-2119

Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLVENTS; ARYLBORONIC ACIDS; BORONIC ACID; CATALYTIC PROCESS; HALIDE COMPLEXES; HYDROXO COMPLEXES; ORGANOBORON; REACTION PATHWAYS; RELATIVE RATES; STOICHIOMETRIC REACTION; SUZUKI-MIYAURA REACTION; SYSTEMATIC STUDY; TRANSMETALATION; WEAK BASE;

EID: 79951832916     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1108326     Document Type: Article
Times cited : (369)

References (32)
  • 1
    • 0036643464 scopus 로고    scopus 로고
    • For a summation of studies of transmetalation in the Suzuki-Miyaura reaction, see
    • For a summation of studies of transmetalation in the Suzuki-Miyaura reaction, see: Miyaura, N. J. Organomet. Chem. 2002, 653, 54-57.
    • (2002) J. Organomet. Chem. , vol.653 , pp. 54-57
    • Miyaura, N.1
  • 9
    • 33745755372 scopus 로고    scopus 로고
    • For data that are consistent with transmetalation by a mechanism involving reaction of a boronic acid with a palladium hydroxide, see: (a)
    • For data that are consistent with transmetalation by a mechanism involving reaction of a boronic acid with a palladium hydroxide, see: (a) Suzaki, Y.; Osakada, K. Organometallics 2006, 25, 3251-3258.
    • (2006) Organometallics , vol.25 , pp. 3251-3258
    • Suzaki, Y.1    Osakada, K.2
  • 13
    • 34247477344 scopus 로고    scopus 로고
    • For studies that highlight the frequent ambiguity of the turnoverlimiting step of the Suzuki-Miyaura reaction, see: (a)
    • For studies that highlight the frequent ambiguity of the turnoverlimiting step of the Suzuki-Miyaura reaction, see: (a) Espino, G.; Kurbangalieva, A.; Brown, J. M. Chem. Commun. 2007, 1742-1744.
    • (2007) Chem. Commun. , pp. 1742-1744
    • Espino, G.1    Kurbangalieva, A.2    Brown, J.M.3
  • 20
    • 79951830779 scopus 로고    scopus 로고
    • note
    • Yields for organic products were determined by GC analysis versus n-tetradecane as internal standard.
  • 21
    • 79951819025 scopus 로고    scopus 로고
    • note
    • A similar reaction was reported previously with no experimental details in reviews by Suzuki and Miyaura. See ref 9.
  • 23
    • 0002812967 scopus 로고    scopus 로고
    • Miyaura, N., Ed.; Springer: Berlin/Heidelberg
    • (b) Miyaura, N. In Cross-Coupling Reactions; Miyaura, N., Ed.; Springer: Berlin/Heidelberg: 2002; Vol. 219, p 11-59.
    • (2002) Cross-Coupling Reactions , vol.219 , pp. 11-59
    • Miyaura, N.1
  • 24
    • 79951830183 scopus 로고    scopus 로고
    • note
    • Aqueous THF mixtures are biphasic in the presence of inorganic base, whereas aqueous acetone mixtures remain homogeneous.
  • 26
    • 79951848285 scopus 로고    scopus 로고
    • note
    • Lloyd-Jones et al. also reported that the population of free boronic acid increases when the concentration of water is decreased.
  • 32
    • 79951819024 scopus 로고    scopus 로고
    • note
    • 3)4 upon warming.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.