Efficient C–N and C–S Bond Formation Using the Highly Active [Ni(allyl)Cl(IPr*OMe)] Precatalyst. Issue 15 (7th March 2014)

• Record Type: Journal Article
• Authors: Martin, Anthony R.; Nelson, David J.; Meiries, Sébastien; Slawin, Alexandra M. Z.; Nolan, Steven P.
• Is Part Of: European journal of organic chemistry. Issue 15(2014)
• Page Start: 3127
• Page End: 3131
• Publication Date: 2014-03-07
• Subjects: Nickel -- Carbene ligands -- Cross‐coupling -- Arenes -- Amination -- Sulfination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402022
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Two new [Ni(allyl)Cl(NHC)] complexes with the bulky yet flexible N‐heterocyclic carbene (NHC) ligands IPr* { N, N′ ‐bis[2, 6‐bis(diphenylmethyl)‐4‐methylphenyl]imidazole‐2‐ylidene} and IPr* OMe { N, N′ ‐bis[2, 6‐bis(diphenylmethyl)‐4‐methoxyphenyl]imidazol‐2‐ylidene} are reported. These complexes were employed in the amination and sulfination of aryl halide species and were shown to perform well in these reactions, which typically required less than half as much catalyst as previous state‐of‐the‐art nickel complexes. Abstract : In the Nick of time: Two [Ni(allyl)Cl(NHC)] complexes with the bulky yet flexible N‐heterocyclic carbene (NHC) ligands IPr* and IPr* OMe are reported. An assessment of the catalytic performance of these complexes in Buchwald–Hartwig and thiophenol arylation reactions is described, with the precatalyst [Ni(allyl)Cl(IPr* OMe )] exhibiting outstanding activity.