(C6F5)3B Catalyzed Chemoselective and ortho-Selective Substitution of Phenols with α-Aryl α-Diazoesters

• Published in: Angewandte Chemie International Edition Vol. 55; no. 47; pp. 14807 - 14811
• Main Authors: Yu, Zhunzhun, Li, Yongfeng, Shi, Jiameng, Ma, Ben, Liu, Lu, Zhang, Junliang
• Format: Journal Article
• Language: English
• Published: Blackwell Publishing Ltd 14-11-2016
• Subjects: boron catalysis; chemoselectivity; C−H functionalization; diazo compounds; phenols
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201608937

The development of an efficient method for the site‐selective substitution of unprotected phenols has long been considered as an attractive but challenging task. Herein, we describe a highly chemo‐ and ortho‐selective substitution reaction of phenols with α‐aryl α‐diazoacetates with commercially available (C6F5)3B as the catalyst. This reaction proceeds under simple and mild conditions with high efficiency, it features a wide substrate scope and can be easily scaled up.
Commercially available (C6F5)3B as the catalyst enables the highly chemo‐ and ortho‐selective substitution of phenols with α‐aryl α‐diazoacetates. This reaction proceeds under simple and mild conditions with high efficiency, features a wide substrate scope, and can be easily scaled up.