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

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 alpha-aryl alpha-diazoacetates with commerci...

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Bibliographic Details
Published inAngewandte 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
LanguageEnglish
Published WEINHEIM Wiley 14.11.2016
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
boron catalysis
chemoselectivity
phenols
ORGANIC-SYNTHESIS
DIAZOACETATES
GOLD CATALYSIS
FRUSTRATED LEWIS PAIRS
DIAZO-COMPOUNDS
C-H functionalization
H BOND FUNCTIONALIZATION
DIAZOCARBONYL COMPOUNDS
N-TOSYLHYDRAZONES
INSERTION REACTIONS
CARBENE INSERTION
diazo compounds
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Summary: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 alpha-aryl alpha-diazoacetates with commercially available (C6F5)(3)B 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201608937