The Triple Role of Fluoride Ions in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unprecedented Transmetalation from [ArPdFL2] Complexes

被引：107

作者：

Amatore, Christian ^{[1
]}

Jutand, Anny ^{[1
]}

Le Duc, Gaetan ^{[1
]}

机构：

[1] UMR CNRS ENS UPMC 8640, Dept Chim, Ecole Normale Super, F-75231 Paris 5, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 06期

关键词：

aryl boronic acid; fluoride ions; palladium; reaction mechanism; Suzuki-Miyaura reactions; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; ARYL CHLORIDES; BORONIC ACID; ELIMINATION; PD(II); BASE;

D O I：

10.1002/anie.201107202

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluoride ions play three roles in the Suzuki-Miyaura reaction. They favor the reaction by formation of trans-[ArPdF(PPh 3) 2], which reacts with Ar B(OH) 2 in an unprecedented rate-determining transmetalation, and by promoting the reductive elimination from the trans-[ArPdAr (PPh 3) 2] intermediate. Conversely, F - disfavors the reaction by formation of unreactive anionic Ar B(OH) n-3F n - (n=1-3), leading to two antagonistic effects of F - in the transmetalation. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1379 / 1382

页数：4

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