Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 2, Pages 587-590Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610715
Keywords
benzimidazoles; cyclization; electrochemistry; heterocycles; radicals
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Funding
- MOST [2016YFA0204100]
- NSFC [21402164, 21672178, 21603227]
- Thousand Youth Talents Plan [K08004]
- XMU [X170300109]
- Fujian province [Z0230106]
- Xiamen [Z0330104]
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We report herein an atom- economical and sustainable approach to access amidinyl radical intermediates through the anodic cleavage of N-H bonds. The resulting nitrogen-centered radicals undergo cyclizations with (hetero) arenes, followed by rearomatization, to afford functionalized tetracyclic benzimidazoles in a highly straightforward and efficient manner. This metal-and reagent-free C-H/N-H cross-coupling reaction exhibits a broad substrate scope and proceeds with high chemoselectivity.
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