Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides

被引：106
|
作者：
Dreher, Spencer D. [1 ,2 ,3 ]
Lim, Siang-Ee [4 ]
Sandrock, Deidre L. [4 ]
Molander, Gary A. [4 ]
机构：
[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
[2] Merck & Co Inc, Catalyt React Discovery, Rahway, NJ 07065 USA
[3] Merck & Co Inc, Dev Lab, Rahway, NJ 07065 USA
[4] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 10期
关键词：
PALLADIUM CATALYSTS; BORONIC ACIDS; HALIDES; DERIVATIVES; ESTERS;
D O I：
10.1021/jo900152n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Parallel microscale experimentation was used to develop general conditions for the Suzuki-Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. These conditions were found to be amenable to coupling with aryl bromides, iodides, and triflates as well. The conditions that were previously identified through similar techniques to promote the cross-coupling of secondary alkyltrifluoroborates with aryl chlorides were not optimal for the primary alkyltrifluoroborates, thus demonstrating the value of parallel experimentation to develop novel, substrate specific results.
引用
收藏
页码：3626 / 3631
页数：6
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