Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air

被引:76
作者
Matoba, K [1 ]
Motofusa, S [1 ]
Cho, CS [1 ]
Ohe, K [1 ]
Uemura, S [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan
关键词
antimony; palladium; oxygen; Heck reaction;
D O I
10.1016/S0022-328X(98)00974-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diphenylantimony chloride and phenylantimony dichloride, mainly the former, react smoothly with alkenes in acetonitrile at r.t. in the presence of a catalytic amount of Pd(OAc)(2) under air to afford the corresponding phenylated alkenes (Heck-type reaction). The addition of AgOAc as reoxidant is not necessary for this reaction in sharp contrast to similar reactions using triarylstibines. The oxygen absorption is confirmed in this catalytic reaction and the reaction does not proceed catalytically in palladium(II) under inert gases, such as nitrogen or argon. Even under air the addition of a radical scavenger stopped the reaction. The regeneration of PhPdOAc species from Ph2SbCl, HPdOAc species and oxygen is proposed as a key step in the catalytic cycle where oxygen-containing radical species might be present as intermediates. (C) 1999 Elsevier Science S.A. All rights reserved.
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页码:3 / 10
页数:8
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