期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 24, 页码 5721-5727出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000962
关键词
C-H functionalization; Gold; Phenothiazine; Diazo compounds; Carbenes
资金
- German Science Foundation
- Dean's Seed Fund of RWTH Aachen Foundation
- Australian Research Council [FT180100260, DP200100063]
- RWTH Aachen University
- Chinese Scholarship Council
- Projekt DEAL
- Australian Research Council [DP200100063, FT180100260] Funding Source: Australian Research Council
Phenothiazine is an important structural motif in pharmaceuticals and advanced functional organic materials. However, the C-H functionalization reaction of N-protected phenothiazine is rather unexplored and often shadowed by its chemical reactivity on the heteroatomic centers, which limits the diversity of its potential applications. This report demonstrates a straightforward approach towards the site-selective C-H functionalization of phenothiazine at the para-position of N atom via gold-catalyzed carbene transfer reactions (37 examples, up to 83% yield). The mechanism behind the regionselectivity of the C-H functionalization reaction was also elucidated by a combination of computational and experimental studies.
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