期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 4, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103341
关键词
Buchwald-Hartwigamination; heterocycles; N-heterocyclic carbenes; palladium
资金
- Natural Science Foundation of Guangdong Province [2018A030313296]
- Hunan Provincial Natural Science Foundation of China [2021JJ40519]
- Key Laboratory of Polymeric Composite & Functional Materials of Ministry of Education [PCFM-2017-03]
- special funds for key disciplines construction from Guangdong and Zhongshan
- Rutgers University
- NSF [CAREER CHE-1650766]
- NIH [1R35GM133326]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
A new class of large-but-flexible Pd-BIAN-NHC catalysts have been designed for the challenging Buchwald-Hartwig amination of coordinating heterocycles, enabling cross-coupling of a variety of heterocycles with different amines under practical aerobic conditions. The study on the ligand structure and electronic properties of the carbene center will facilitate the discovery of more active catalyst systems based on the unique BIAN-NHC scaffold.
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.
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