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

15 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

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

Access

10.1021/acs.orglett.9b01620

OpenUrl availability

Full text

Cite this

@article{9e0ecc9a76f248588a7b7e836f7aec33,

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 = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jun,

day = "21",

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

language = "English (US)",

volume = "21",

pages = "4734--4738",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides

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.

UR - http://www.scopus.com/inward/record.url?scp=85067695253&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85067695253&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b01620

DO - 10.1021/acs.orglett.9b01620

M3 - Article

C2 - 31190545

AN - SCOPUS:85067695253

SN - 1523-7060

VL - 21

SP - 4734

EP - 4738

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

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

Abstract

Bibliographical note

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this