General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

Yang Wang; Vladimir Gevorgyan

doi:10.1002/anie.201410375

General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

Yang Wang, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.

Original language	English (US)
Pages (from-to)	2255-2259
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	7
DOIs	https://doi.org/10.1002/anie.201410375
State	Published - Feb 9 2015
Externally published	Yes

Keywords

C-H activation
Carboxylation
Palladium
Phenols
Salicylic acids

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201410375

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abstract = "A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.",

keywords = "C-H activation, Carboxylation, Palladium, Phenols, Salicylic acids",

author = "Yang Wang and Vladimir Gevorgyan",

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AU - Wang, Yang

AU - Gevorgyan, Vladimir

PY - 2015/2/9

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N2 - A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.

AB - A silanol-directed, palladium-catalyzed C-H carboxylation reaction of phenols to give salicylic acids has been developed. This method features high efficiency and selectivity, and excellent functional-group tolerance. The generality of this method was demonstrated by the carboxylation of estrone and by the synthesis of an unsymmetrically o,o′-disubstituted phenolic compound through two sequential C-H functionalization processes.

KW - C-H activation

KW - Carboxylation

KW - Palladium

KW - Phenols

KW - Salicylic acids

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JO - Angewandte Chemie - International Edition

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IS - 7

ER -

General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

Abstract

Keywords

ASJC Scopus subject areas

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