NHC/Phosphite Nickel(II) Precatalysts for the C-N Cross-Coupling of (Hetero)Aryl Chlorides under Mild Conditions

TitleNHC/Phosphite Nickel(II) Precatalysts for the C-N Cross-Coupling of (Hetero)Aryl Chlorides under Mild Conditions
Publication TypeJournal Article
Year of Publication2025
AuthorsDarandale, NR, John, ME, Moggach, SA, Sawant, DN, Koutsantonis, GA, Dorta, R, Stewart, SG
JournalORGANIC LETTERS
Volume27
Issue37
Pagination10526-10531
Date PublishedSEP
Type of ArticleArticle
ISSN1523-7060
Abstract

We report the synthesis of three nickel complexes based on Ni(NHC)[P(OR)3](Ar)Cl and their application in C(sp 2)-N cross-coupling reactions. Reactions involving secondary amines proceeded at room temperature, while anilines and primary alkyl amines coupled under mild heating. The reported complexes are air-stable as solids, operate at low catalytic loading, and do not require an exogenous ligand. Mechanistic studies suggest both free and Ni-bound phosphite are present during the reaction and that an isolated [Ni(NHC)(amine)(Ar)Cl] complex could be an on-cycle, catalytically active species.

DOI10.1021/acs.orglett.5c03230
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.6

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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