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

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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)4734-4738
Number of pages5
JournalOrganic Letters
Volume21
Issue number12
DOIs
StatePublished - Jun 21 2019

Fingerprint

cross coupling
Palladium
Chlorides
palladium
Salts
chlorides
carboxylates
Silver
Carbon Dioxide
Sodium Chloride
salts
Byproducts
Copper
Sodium
sodium chlorides
Catalysts
carbon dioxide
Substrates
silver
sodium

PubMed: MeSH publication types

  • Journal Article

Cite this

Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides. / Daley, Ryan A.; Liu, En Chih; Topczewski, Joseph J.

In: Organic Letters, Vol. 21, No. 12, 21.06.2019, p. 4734-4738.

Research output: Contribution to journalArticle

@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}",
year = "2019",
month = "6",
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

VL - 21

SP - 4734

EP - 4738

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 12

ER -