Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides

Ryan A. Daley; En Chih Liu; Joseph J. Topczewski

doi:10.1021/acs.orglett.9b01620

Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides

Ryan A. Daley, En Chih Liu, Joseph J. Topczewski

Chemistry (Twin Cities)

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

16 Scopus citations

Abstract

The cross-coupling of sodium (hetero)aryl carboxylates with (hetero)aryl chlorides proceeds with 1 mol % palladium catalyst and does not require inorganic base, silver salts, or copper salts. This coupling uses two low energy partners, and the only stoichiometric byproducts are carbon dioxide and sodium chloride. The substrate scope includes less activated aryl chlorides and carboxylates (>25 examples). The palladium loading could be reduced to 0.1 mol %, and Buchwald-style precatalysts could be used.

Original language	English (US)
Pages (from-to)	4734-4738
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.9b01620
State	Published - Jun 21 2019

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Funding Information:
Financial support was provided by the University of Minnesota.

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© 2019 American Chemical Society.

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title = "Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides",

abstract = "The cross-coupling of sodium (hetero)aryl carboxylates with (hetero)aryl chlorides proceeds with 1 mol % palladium catalyst and does not require inorganic base, silver salts, or copper salts. This coupling uses two low energy partners, and the only stoichiometric byproducts are carbon dioxide and sodium chloride. The substrate scope includes less activated aryl chlorides and carboxylates (>25 examples). The palladium loading could be reduced to 0.1 mol %, and Buchwald-style precatalysts could be used.",

author = "Daley, {Ryan A.} and Liu, {En Chih} and Topczewski, {Joseph J.}",

note = "Funding Information: Financial support was provided by the University of Minnesota. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b01620",

language = "English (US)",

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AU - Daley, Ryan A.

AU - Liu, En Chih

AU - Topczewski, Joseph J.

PY - 2019/6/21

Y1 - 2019/6/21

N2 - The cross-coupling of sodium (hetero)aryl carboxylates with (hetero)aryl chlorides proceeds with 1 mol % palladium catalyst and does not require inorganic base, silver salts, or copper salts. This coupling uses two low energy partners, and the only stoichiometric byproducts are carbon dioxide and sodium chloride. The substrate scope includes less activated aryl chlorides and carboxylates (>25 examples). The palladium loading could be reduced to 0.1 mol %, and Buchwald-style precatalysts could be used.

AB - The cross-coupling of sodium (hetero)aryl carboxylates with (hetero)aryl chlorides proceeds with 1 mol % palladium catalyst and does not require inorganic base, silver salts, or copper salts. This coupling uses two low energy partners, and the only stoichiometric byproducts are carbon dioxide and sodium chloride. The substrate scope includes less activated aryl chlorides and carboxylates (>25 examples). The palladium loading could be reduced to 0.1 mol %, and Buchwald-style precatalysts could be used.

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JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides

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