Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 27, Pages 9017-9021Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201904931
Keywords
benzimidazolones; benzoxazolones; cyclization; electrochemistry; radical reactions
Categories
Funding
- MOST [2016YFA0204100]
- NSFC [21672178]
- Fundamental Research Funds for the Central Universities
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Benzimidazolone and benzoxazolone moieties are important scaffolds in a variety of pharmaceutical molecules. These bicyclic heterocycles are usually prepared from a benzene derivative through the construction of an additional five-membered heterocyclic ring. We report herein a method that enables the efficient synthesis of highly substituted benzimidazolone and benzoxazolone derivatives by building both the benzene and the heterocyclic rings through a dehydrogenative cyclization cascade. Readily available arylamine-tethered 1,5-enynes undergo a biscyclization/dehydrogenation cascade to afford functionalized benzanellated heterocycles in a single step with complete control of regioselectivity. These electricity-powered oxidative transformations proceed with H-2 evolution, thus obviating the need for transition-metal-based catalysts and oxidizing reagents.
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