Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

Christian A. Malapit; Naoko Ichiishi; Melanie S. Sanford

doi:10.1021/acs.orglett.7b02024

Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

Christian A. Malapit, Naoko Ichiishi, Melanie S. Sanford^*

^*Corresponding author for this work

Chemistry

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

78 Scopus citations

Abstract

This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd⁰/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

Original language	English (US)
Pages (from-to)	4142-4145
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.7b02024
State	Published - Aug 4 2017

Funding

We acknowledge financial support from NIH NIGMS (GM073836) and the Danish National Research Foundation (Carbon Dioxide Activation Center; CADIAC) for support. We also thank James Bour (University of Michigan) for helpful discussions.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides",

abstract = "This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.",

author = "Malapit, \{Christian A.\} and Naoko Ichiishi and Sanford, \{Melanie S.\}",

note = "Funding Information: We acknowledge financial support from NIH NIGMS (GM073836) and the Danish National Research Foundation (Carbon Dioxide Activation Center; CADIAC) for support. We also thank James Bour (University of Michigan) for helpful discussions. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b02024",

language = "English (US)",

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T1 - Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

AU - Malapit, Christian A.

AU - Ichiishi, Naoko

AU - Sanford, Melanie S.

N1 - Funding Information: We acknowledge financial support from NIH NIGMS (GM073836) and the Danish National Research Foundation (Carbon Dioxide Activation Center; CADIAC) for support. We also thank James Bour (University of Michigan) for helpful discussions. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/8/4

Y1 - 2017/8/4

N2 - This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

AB - This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

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Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

Abstract

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ASJC Scopus subject areas

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