Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 5, Pages 1117-1123Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801303
Keywords
benzotriazoles; N-2-olefination; alkenes; N-iodosuccinimide; transition-metal-free
Categories
Funding
- National Natural Science Foundation of China [21702105]
- Natural Science Foundation of Jiangsu Province, China [BK20170981]
- Nanjing Tech University
- SICAM Fellowship by Jiangsu National Synergetic Innovation Center for Advanced Materials
- Science and Technology Research Project of Henan Province [162300410197, 182102310623]
- Scientific Research Innovation Foundation of Zhoukou Normal University [ZKNUA201802, ZKNUA201701]
Ask authors/readers for more resources
Herein, we describe a zinc-catalysed N-2-selective olefination of benzotriazoles with unactivated alkenes and styrenes. The transformation is achieved by a N-iodosuccinimide (NIS)-mediated two-step, one-pot approach, proceeding through sequential regioselective -iodoalkylation of benzotriazoles with alkenes and a subsequent base-promoted 1,2-elimination. The N-2-selective -iodoalkylation of benzotriazoles is highly stereospecific and works under very simple and mild conditions, exhibiting excellent functional group tolerance. The high N-2-selectivity is attributed to intermolecular hydrogen bonding between the N-iodosuccinimide and the NH hydrogen bond donor at the 1-position of the benzotriazoles. This scalable process, serving as an efficient method for modular assembly of structurally diverse N-2-olefinated benzotriazoles, will significantly contribute to the chemistry of N-2-functionization of benzotriazoles.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available