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- Title
Buchwald‐Hartwig Amination of Coordinating Heterocycles Enabled by Large‐but‐Flexible Pd‐BIAN‐NHC Catalysts**.
- Authors
Li, Dong‐Hui; Lan, Xiao‐Bing; Song, A‐Xiang; Rahman, Md. Mahbubur; Xu, Chang; Huang, Fei‐Dong; Szostak, Roman; Szostak, Michal; Liu, Feng‐Shou
- Abstract
A new class of large‐but‐flexible Pd‐BIAN‐NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N‐heterocyclic carbene) has been rationally designed to enable the challenging Buchwald‐Hartwig amination of coordinating heterocycles. This robust class of BIAN‐NHC catalysts permits cross‐coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron‐deficient heterocycles containing multiple heteroatoms with BIAN‐INon (N,N′‐bis(2,6‐di(4‐heptyl)phenyl)‐7H‐acenaphtho[1,2‐d]imidazol‐8‐ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN‐NHC scaffold.
- Subjects
HETEROCYCLIC compounds; AMINATION; ELECTRONIC structure; OXAZOLES; THIAZOLES; PALLADIUM catalysts; ARYL chlorides
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 4, p1
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.202103341