Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides

Surendra Thapa, Arjun Kafle, Santosh K. Gurung, Adam Montoya, Patrick Riedel, Ramesh Giri

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.

Original languageEnglish (US)
Pages (from-to)8236-8240
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number28
DOIs
StatePublished - Jul 1 2015

Fingerprint

Iodides
Copper
Ligands
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Thapa, Surendra ; Kafle, Arjun ; Gurung, Santosh K. ; Montoya, Adam ; Riedel, Patrick ; Giri, Ramesh. / Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 28. pp. 8236-8240.
@article{b78a4c33cb2a47fbade298f67c40ef0e,
title = "Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides",
abstract = "Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.",
author = "Surendra Thapa and Arjun Kafle and Gurung, {Santosh K.} and Adam Montoya and Patrick Riedel and Ramesh Giri",
year = "2015",
month = "7",
day = "1",
doi = "10.1002/anie.201502379",
language = "English (US)",
volume = "54",
pages = "8236--8240",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "28",

}

Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides. / Thapa, Surendra; Kafle, Arjun; Gurung, Santosh K.; Montoya, Adam; Riedel, Patrick; Giri, Ramesh.

In: Angewandte Chemie - International Edition, Vol. 54, No. 28, 01.07.2015, p. 8236-8240.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides

AU - Thapa, Surendra

AU - Kafle, Arjun

AU - Gurung, Santosh K.

AU - Montoya, Adam

AU - Riedel, Patrick

AU - Giri, Ramesh

PY - 2015/7/1

Y1 - 2015/7/1

N2 - Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.

AB - Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.

UR - http://www.scopus.com/inward/record.url?scp=85027952836&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027952836&partnerID=8YFLogxK

U2 - 10.1002/anie.201502379

DO - 10.1002/anie.201502379

M3 - Article

AN - SCOPUS:85027952836

VL - 54

SP - 8236

EP - 8240

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 28

ER -