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Volumn 689, Issue 23, 2004, Pages 3820-3830

Rh-catalyzed addition of boronic acids to alkynes for the synthesis of trisubstituted alkenes in a biphasic system - Mechanistic study and recycling of the Rh/m-TPPTC catalyst

Author keywords

Arylation of alkynes; Boronic acids; Homogeneous biphasic catalysis; Rhodium; Water soluble ligand

Indexed keywords

CATALYSIS; CATALYSTS; COMPLEXATION; HYDROPHOBICITY; OLEFINS; REACTION KINETICS; RECYCLING; RHODIUM; SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TOLUENE; WATER;

EID: 12344315039     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.07.025     Document Type: Article
Times cited : (59)

References (78)
  • 8
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    • Modern Solvent in Organic Synthesis
    • P. Knochel Springer Berlin
    • D. Sinou P. Knochel Modern Solvent in Organic Synthesis Topics in Current Chemistry vol. 206 1999 Springer Berlin 41
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    • Sinou, D.1
  • 12
    • 19344371666 scopus 로고    scopus 로고
    • note
    • Abbreviations: TPPTS = trisodium salt of 3,3′,3″- phosphanetriylbenzenesulfonic acid, TPPTC = trilithium salt of 3,3′,3″-phosphanetriylbenzenecarboxylic acid, TPPDS = dipotassium salt of 4,4′-phosphanediylbenzenesulfonic acid
  • 40
    • 0041738169 scopus 로고    scopus 로고
    • For a recent review on asymmetric 1,4-addition, see: T. Hayashi, and K. Yamasaki Chem. Rev. 103 2003 2829
    • (2003) Chem. Rev. , vol.103 , pp. 2829
    • Hayashi, T.1    Yamasaki, K.2
  • 43
    • 0000604304 scopus 로고    scopus 로고
    • SDS surfactant was advocated for the arylation of pyridyl substituted alkynes: M. Lautens, and M. Yoshida Org. Lett. 4 2002 123
    • (2002) Org. Lett. , vol.4 , pp. 123
    • Lautens, M.1    Yoshida, M.2
  • 49
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    • note
    • 1H NMR analysis and gas chromatography. No traces of trimer were detected
  • 54
    • 0037243669 scopus 로고    scopus 로고
    • For a recent review on Rh-catalyzed reactions, see: K. Fagnou, and M. Lautens Chem. Rev. 103 2003 169
    • (2003) Chem. Rev. , vol.103 , pp. 169
    • Fagnou, K.1    Lautens, M.2
  • 61
    • 19344371371 scopus 로고    scopus 로고
    • The requisite substituted alkynes have been prepared by Sonogashira's cross-couplings (unpublished results)
    • The requisite substituted alkynes have been prepared by Sonogashira's cross-couplings (unpublished results)
  • 69
    • 19344371185 scopus 로고    scopus 로고
    • note
    • The hydrolysis of the vinylrhodium intermediate by the boronic acid was negligible (5% of protic source)
  • 70
    • 19344365818 scopus 로고    scopus 로고
    • note
    • 1H NMR experiments for alkenes 3a, 11a, 18a


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.