Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

Wing Yiu Yu; Wing Nga Sit; Zhongyuan Zhou; Albert S.C. Chan

doi:10.1021/ol900756g

Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

Wing Yiu Yu, Wing Nga Sit, Zhongyuan Zhou, Albert S.C. Chan

Research output: Journal article publication › Journal article › Academic research › peer-review

179 Citations (Scopus)

Abstract

A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

Original language	English
Pages (from-to)	3174-3177
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	15
DOIs	https://doi.org/10.1021/ol900756g
Publication status	Published - 6 Aug 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol900756g

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abstract = "A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.",

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AU - Sit, Wing Nga

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AU - Chan, Albert S.C.

PY - 2009/8/6

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N2 - A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

AB - A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

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DO - 10.1021/ol900756g

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Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

Abstract

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