Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides

Shuichi Oi; Shun Ichiro Watanabe; Susumu Fukita; Yoshio Inoue

doi:10.1016/j.tetlet.2003.09.151

Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides

Shuichi Oi, Shun Ichiro Watanabe, Susumu Fukita, Yoshio Inoue

Environment Conservation Center

Tohoku University

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

148 Citations (Scopus)

Abstract

Direct ortho arylation of phenols with aryl bromides catalyzed by a rhodium complex and hexamethylphosphorous triamide (HMPT) have been developed. A plausible reaction mechanism involving in situ generation of arylphosphites from phenols and HMPT, phosphorus-directed ortho metalation, and transesterification of the arylated arylphosphites with the substrate phenols is proposed.

Original language	English
Pages (from-to)	8665-8668
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2003.09.151
Publication status	Published - 2003 Nov 24

Keywords

Aryl halide
Arylation
Phenol
Rhodium catalyst

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10.1016/j.tetlet.2003.09.151

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AU - Oi, Shuichi

AU - Watanabe, Shun Ichiro

AU - Fukita, Susumu

AU - Inoue, Yoshio

PY - 2003/11/24

Y1 - 2003/11/24

N2 - Direct ortho arylation of phenols with aryl bromides catalyzed by a rhodium complex and hexamethylphosphorous triamide (HMPT) have been developed. A plausible reaction mechanism involving in situ generation of arylphosphites from phenols and HMPT, phosphorus-directed ortho metalation, and transesterification of the arylated arylphosphites with the substrate phenols is proposed.

AB - Direct ortho arylation of phenols with aryl bromides catalyzed by a rhodium complex and hexamethylphosphorous triamide (HMPT) have been developed. A plausible reaction mechanism involving in situ generation of arylphosphites from phenols and HMPT, phosphorus-directed ortho metalation, and transesterification of the arylated arylphosphites with the substrate phenols is proposed.

KW - Aryl halide

KW - Arylation

KW - Phenol

KW - Rhodium catalyst

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ER -

Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides

Abstract

Keywords

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