MECHANISMS OF THE PALLADIUM-CATALYZED COUPLINGS OF ACID-CHLORIDES WITH ORGANOTIN REAGENTS
MECHANISMS OF THE PALLADIUM-CATALYZED COUPLINGS OF ACID-CHLORIDES WITH ORGANOTIN REAGENTS
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DOI：
10.1021/ja00357a026
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发表时间：
1983-01-01
影响因子：
15
通讯作者：
STILLE, JK
中科院分区：
文献类型：
--
作者：
LABADIE, JW;STILLE, JK
In the coupling reaction of benzoyl chloride with phenyltributyltin catalyzed by the introduction of benzyl-chlorobis (triphenylphosphine) palladium (II)(1), thedisappearance of 1 was observed in the 31P spectrum of the reaction mixture with the appearance of benzoylchlorobis (triphenylphosphine) palladium (II)(3); benzophenone was obtained as a product of the reaction. The reaction of 3 with phenyltributyltin also yields benzophenone and is retarded by added triphenylphosphine. The results are consistent with a catalytic cycle involving sequential fast oxidative addition of benzoyl chloride to a palladium (O) complex (generated from 1) to give 3, slow transmetalation of 3 with the tin reagent, and fast reductive elimination to regenerate the palladium (O) complex. The rates of the transmetalation reaction of unsymmetrical organotrimethyltin or organotributyltin (R'SnRj) with 3 in the catalytic reaction followed the order R'=
