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- Title
Copper-Mediated Late-Stage Functionalization of Heterocycle-Containing Molecules.
- Authors
Shang, Ming; Wang, Ming‐Ming; Saint‐Denis, Tyler G.; Li, Ming‐Hong; Dai, Hui‐Xiong; Yu, Jin‐Quan
- Abstract
One long-standing issue in directed C−H functionalization is that either nitrogen or sulfur atoms present in heterocyclic substrates may bind preferentially to a transition-metal catalyst rather than to the desired directing group. This competitive binding has largely hindered the application of C−H functionalization in late-stage heterocycle drug discovery. Reported here is the use of an oxazoline-based directing group capable of overriding the poisoning effect of a wide range of heterocycle substrates. The potential use of this directing group in pharmaceutical drug discovery is illustrated by diversification of Telmisartan (an antagonist for the angiotensin II receptor) through copper-mediated C−H amination, hydroxylation, thiolation, arylation, and trifluoromethylation.
- Subjects
NITROGEN; SULFUR; METAL catalysts; HETEROCYCLIC compounds; ORGANIC cyclic compounds
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 19, p5401
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201611287