» Articles » PMID: 23627776

Nickel-catalyzed Suzuki-Miyaura Coupling of Heteroaryl Ethers with Arylboronic Acids

Overview
Journal J Org Chem
Specialty Chemistry
Date 2013 May 1
PMID 23627776
Citations 11
Authors
Affiliations
Soon will be listed here.
Abstract

Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids was described. Selective activation of the phenol C-O bonds was achieved by converting them into the corresponding aryl 2,4-dimethoxy-1,3,5-triazine-6-yl ethers, in which aryl C-O bond could be selectively cleaved with inexpensive, air-stable NiCl2(dppf) as a catalyst. Coupling of these readily accessible heteroaryl ethers proved tolerant of extensive functional groups.

Citing Articles

Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki-Miyaura and Related C-C Couplings.

Perney J, Humblot-Negri A, Vaca-Garcia C, Lemouzy S, Urrutigoity M Molecules. 2025; 30(1.

PMID: 39795108 PMC: 11721199. DOI: 10.3390/molecules30010051.


Transition metal-catalysed A-ring C-H activations and C(sp)-C(sp) couplings in the 13α-oestrone series and evaluation of antiproliferative properties.

Traj P, Abdolkhaliq A, Nemeth A, Dajcs S, Tomosi F, Lanisnik-Rizner T J Enzyme Inhib Med Chem. 2021; 36(1):895-902.

PMID: 33771084 PMC: 8008932. DOI: 10.1080/14756366.2021.1900165.


Small Phosphine Ligands Enable Selective Oxidative Addition of Ar-O over Ar-Cl Bonds at Nickel(0).

Entz E, Russell J, Hooker L, Neufeldt S J Am Chem Soc. 2020; 142(36):15454-15463.

PMID: 32805116 PMC: 8082739. DOI: 10.1021/jacs.0c06995.


Nickel(II) Nanoparticles Immobilized on EDTA-Modified FeO@SiO Nanospheres as Efficient and Recyclable Catalysts for Ligand-Free Suzuki-Miyaura Coupling of Aryl Carbamates and Sulfamates.

Inaloo I, Majnooni S, Eslahi H, Esmaeilpour M ACS Omega. 2020; 5(13):7406-7417.

PMID: 32280882 PMC: 7144170. DOI: 10.1021/acsomega.9b04450.


Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles.

Russell J, Entz E, Joyce I, Neufeldt S ACS Catal. 2019; 9(4):3304-3310.

PMID: 31057986 PMC: 6497415. DOI: 10.1021/acscatal.9b00744.