Ligand-accelerated ortho -C-H alkylation of arylcarboxylic acids using alkyl boron reagents

Peter S. Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin Quan Yu

doi:10.1021/ja409014v

Ligand-accelerated ortho -C-H alkylation of arylcarboxylic acids using alkyl boron reagents

Peter S. Thuy-Boun, Giorgio Villa, Devin Dang, Paul Richardson, Shun Su, Jin Quan Yu

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

131 Scopus citations

Abstract

A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.

Original language	English
Pages (from-to)	17508-17513
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	135
Issue number	46
DOIs	https://doi.org/10.1021/ja409014v
State	Published - 20 Nov 2013
Externally published	Yes

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10.1021/ja409014v

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title = "Ligand-accelerated ortho -C-H alkylation of arylcarboxylic acids using alkyl boron reagents",

abstract = "A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.",

author = "Thuy-Boun, {Peter S.} and Giorgio Villa and Devin Dang and Paul Richardson and Shun Su and Yu, {Jin Quan}",

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T1 - Ligand-accelerated ortho -C-H alkylation of arylcarboxylic acids using alkyl boron reagents

AU - Thuy-Boun, Peter S.

AU - Villa, Giorgio

AU - Dang, Devin

AU - Richardson, Paul

AU - Su, Shun

AU - Yu, Jin Quan

PY - 2013/11/20

Y1 - 2013/11/20

N2 - A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.

AB - A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.

UR - http://www.scopus.com/inward/record.url?scp=84888387927&partnerID=8YFLogxK

U2 - 10.1021/ja409014v

DO - 10.1021/ja409014v

M3 - Article

C2 - 24124892

AN - SCOPUS:84888387927

SN - 0002-7863

VL - 135

SP - 17508

EP - 17513

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 46

ER -

Ligand-accelerated ortho -C-H alkylation of arylcarboxylic acids using alkyl boron reagents

Abstract

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