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

189 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

More information

10.1021/ol900756g

Cite this

@article{5cac7cc6dfc5448e9aa028989dd0c0d1,

title = "Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides",

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.",

author = "Yu, \{Wing Yiu\} and Sit, \{Wing Nga\} and Zhongyuan Zhou and Chan, \{Albert S.C.\}",

year = "2009",

month = aug,

day = "6",

doi = "10.1021/ol900756g",

language = "English",

volume = "11",

pages = "3174--3177",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

AU - Yu, Wing Yiu

AU - Sit, Wing Nga

AU - Zhou, Zhongyuan

AU - Chan, Albert S.C.

PY - 2009/8/6

Y1 - 2009/8/6

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.

UR - https://www.scopus.com/pages/publications/68149126733

U2 - 10.1021/ol900756g

DO - 10.1021/ol900756g

M3 - Journal article

C2 - 19583200

SN - 1523-7060

VL - 11

SP - 3174

EP - 3177

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

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

Abstract

ASJC Scopus subject areas

More information

Other files and links

Fingerprint

Cite this