메뉴 건너뛰기




Volumn 20, Issue 41, 2014, Pages 13146-13149

Palladium-Catalyzed Cross-Coupling of Unactivated Aryl Sulfides with Arylzinc Reagents under Mild Conditions

Author keywords

C S bond activation; cross coupling; organosulfur compounds; organozinc compounds; palladium

Indexed keywords

CHEMICAL BONDS; ORGANIC COMPOUNDS; ORGANOMETALLICS; PALLADIUM; SULFUR COMPOUNDS;

EID: 84941112671     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404380     Document Type: Article
Times cited : (56)

References (140)
  • 2
    • 20544450502 scopus 로고    scopus 로고
    • (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim
    • Metal-Catalyzed Cross-Coupling Reactions (Eds.:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004;
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 3
    • 84881498225 scopus 로고    scopus 로고
    • (Ed.: Y. Nishihara), Springer, Heidelberg
    • Applied Cross-Coupling Reactions, (Ed.:, Y. Nishihara,), Springer, Heidelberg, 2013;
    • (2013) Applied Cross-Coupling Reactions
  • 112
    • 84957897182 scopus 로고    scopus 로고
    • We could reduce the amounts of the palladium catalyst and an arylzinc reagent without significant decrease of yield. For instance, the reaction of thioanisole with 4-ethoxycarbonylphenylzinc reagent (1.4 equiv) in the presence of 3 mol % of [Pd-PEPPSI-SIPr] proceed to completion in 7 h to afford 1 a in 87 % yield.
    • We could reduce the amounts of the palladium catalyst and an arylzinc reagent without significant decrease of yield. For instance, the reaction of thioanisole with 4-ethoxycarbonylphenylzinc reagent (1.4 equiv) in the presence of 3 mol % of [Pd-PEPPSI-SIPr] proceed to completion in 7 h to afford 1 a in 87 % yield.
  • 113
    • 84907458127 scopus 로고    scopus 로고
    • The success of Negishi coupling heavily depends on the nature of the organozinc species (i.e., the presence or absence of LiCl). For details, see
    • The success of Negishi coupling heavily depends on the nature of the organozinc species (i.e., the presence or absence of LiCl). For details, see:, L. C. McCann, M. G. Organ, Angew. Chem. 2014, 126, 4475;
    • (2014) Angew. Chem. , vol.126 , pp. 4475
    • McCann, L.C.1    Organ, M.G.2
  • 114
    • 84899429091 scopus 로고    scopus 로고
    • references therein.
    • Angew. Chem. Int. Ed. 2014, 53, 4386, and references therein.
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4386
  • 136
    • 84957897183 scopus 로고    scopus 로고
    • The same reaction at 20 'C was complicated due to undesired arylation at the chlorinated position.
    • The same reaction at 20 'C was complicated due to undesired arylation at the chlorinated position.
  • 137
    • 84957897184 scopus 로고    scopus 로고
    • 4-Bromothioanisole underwent arylation at the brominated carbon exclusively.
    • 4-Bromothioanisole underwent arylation at the brominated carbon exclusively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.