Control of reactive site in palladium-catalyzed Grignard cross-coupling of arenes containing both bromide and triflate

被引:83
作者
Kamikawa, T [1 ]
Hayashi, T [1 ]
机构
[1] KYOTO UNIV,FAC SCI,DEPT CHEM,SAKYO KU,KYOTO 60601,JAPAN
关键词
D O I
10.1016/S0040-4039(97)01655-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of 4-bromophenyl triflate (1) with phenylmagnesium bromide in the presence of 5 mol % of PdCl2(dppp) gave 97% yield of 4-bromobiphenyl (2a), which was formed by selective replacement of triflate in 1 by phenyl. On the other hand, bromide in 1 was substituted with the phenyl Grignard reagent selectively by use of PdCl2(meo-mop)(2) to give 4-biphenyl triflate (3a) in high yield. The selective substitution was demonstrated to take place at the oxidative addition step to a palladium(0) species in a stoichiometric reaction of 1 with palladium(0) phosphine complexes. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7087 / 7090
页数:4
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