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

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35 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2255-2259
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number7
DOIs
StatePublished - Feb 9 2015
Externally publishedYes

Fingerprint

Carboxylation
Salicylic acid
Salicylates
Phenols
Palladium
Estrone
Functional groups
silanol

Keywords

  • C-H activation
  • Carboxylation
  • Palladium
  • Phenols
  • Salicylic acids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

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title = "General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation",
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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T1 - General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation

AU - Wang, Yang

AU - Gevorgyan, Vladimir

PY - 2015/2/9

Y1 - 2015/2/9

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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DO - 10.1002/anie.201410375

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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