(C sub(6)F sub(5)) sub(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 commer...

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Published inAngewandte Chemie Vol. 128; no. 47; pp. 15027 - 15031
Main Authors Yu, Zhunzhun, Li, Yongfeng, Shi, Jiameng, Ma, Ben, Liu, Lu, Zhang, Junliang
Format Journal Article
LanguageEnglish
Published 01.11.2016
Subjects
Catalysts
Efficiency
Phenols
Substitution reactions
Substrates
Tasks
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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 (C sub(6)F sub(5)) sub(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.Original Abstract: Herausforderung gemeistert: Kommerziell erhaeltliches (C sub(6)F sub(5)) sub(3)B als Katalysator ermoglicht die chemo- und ortho-selektive Substitution von Phenolen mit [alpha]-Aryl-[alpha]-diazoacetaten. Die Reaktion laeuft unter milden Bedingungen mit hoher Effizienz ab, zeichnet sich durch eine grose Substratbreite aus und kann leicht skaliert werden.
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201608937