A general catalyst for the β-selective C - H bond arylation of thiophenes with iodoarenes

Kirika Ueda; Shuichi Yanagisawa; Junichiro Yamaguchi; Kenichiro Itami

doi:10.1002/anie.201005082

A general catalyst for the β-selective C - H bond arylation of thiophenes with iodoarenes

Kirika Ueda, Shuichi Yanagisawa, Junichiro Yamaguchi, Kenichiro Itami

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

192 Citations (Scopus)

Abstract

Open access: The normally less-reactive β position of thiophenes was previously inaccessible to direct functionalization. However, the β selectivity observed with the catalytic system PdCl₂/P{OCH(CF ₃)₂}₃/Ag₂CO₃ in the arylation of thiophenes with iodoarenes (see scheme) is a remarkably general phenomenon applicable to unsubstituted, monosubstituted, and disubstituted thiophene derivatives, as well as thiophene-containing fused aromatic compounds.

Original language	English
Pages (from-to)	8946-8949
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	47
DOIs	https://doi.org/10.1002/anie.201005082
Publication status	Published - 2010 Nov 15
Externally published	Yes

Keywords

C - C coupling
homogeneous catalysis
palladium
regioselectivity
thiophenes

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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abstract = "Open access: The normally less-reactive β position of thiophenes was previously inaccessible to direct functionalization. However, the β selectivity observed with the catalytic system PdCl2/P{OCH(CF 3)2}3/Ag2CO3 in the arylation of thiophenes with iodoarenes (see scheme) is a remarkably general phenomenon applicable to unsubstituted, monosubstituted, and disubstituted thiophene derivatives, as well as thiophene-containing fused aromatic compounds.",

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T1 - A general catalyst for the β-selective C - H bond arylation of thiophenes with iodoarenes

AU - Ueda, Kirika

AU - Yanagisawa, Shuichi

AU - Yamaguchi, Junichiro

AU - Itami, Kenichiro

PY - 2010/11/15

Y1 - 2010/11/15

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AB - Open access: The normally less-reactive β position of thiophenes was previously inaccessible to direct functionalization. However, the β selectivity observed with the catalytic system PdCl2/P{OCH(CF 3)2}3/Ag2CO3 in the arylation of thiophenes with iodoarenes (see scheme) is a remarkably general phenomenon applicable to unsubstituted, monosubstituted, and disubstituted thiophene derivatives, as well as thiophene-containing fused aromatic compounds.

KW - C - C coupling

KW - homogeneous catalysis

KW - palladium

KW - regioselectivity

KW - thiophenes

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