Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation

被引：209

作者：

Dreher, Spencer D. ^{[1
,2
]}

Dormer, Peter G. ^{[1
,2
]}

Sandrock, Deidre L. ^{[3
]}

Molander, Gary A. ^{[3
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

[2] Merck & Co Inc, Catalyt React Discovery & Dev Lab, Rahway, NJ 07065 USA

[3] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 29期

关键词：

D O I：

10.1021/ja8031423

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Microscale parallel experimentation was used to discover three catalyst systems capable of coupling secondary organotrifluoroborates with sterically and electronically demanding aryl chlorides and bromides. The ensuing results represent the first comprehensive study of alkylboron coupling to aryl chlorides and, in particular, using secondary alkylboron partners. A ligand-dependent beta-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases.

引用

页码：9257 / +

页数：4

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