Regioselectivity of the rhodium-catalyzed hydroboration of vinyl arenes: Electronic twists and mechanistic shifts

被引：54

作者：

Edwards, David R.

Hleba, Yonek B.

Lata, Christopher J.

Calhoun, Larry A.

Crudden, Cathleen M. ^{[1
]}

机构：

[1] Queens Univ, Kingston, ON K7L 3N6, Canada

[2] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5E2, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 41期

关键词：

Hammett substituent parameter; hydroboration; kinetic isotope effect; rhodium; vinyl arenes;

D O I：

10.1002/anie.200702563

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Any substituent does it: The hydroboration of vinyl arenes with pinacol borane (HBPin) and cationic rhodium complexes selectively placed the boron proximal to the aryl rather than phenyl ring, regardless of whether this ring bears electron-donating or electron-withdrawing substituents. In competition experiments between styrene and various vinyl arenes, preferential hydroboration also occured at the substituted arene (see scheme). Hammett plots indicate a break in the mechanism. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7799 / 7802

页数：4

共 47 条

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