Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 19, Pages 12963-12974Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01519
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Funding
- National Natural Science Foundation of China [22001272, 31902419]
- Science and Technology Research Project of Henan Province [222102110165]
- Young and Middle-Aged Backbone Teachers of Zhoukou Normal University, Science and Technology Leader of Zhoukou Normal University
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This study reports a new method for N-2-selective beta-thioalkylation of benzotriazoles with unactivated alkenes and styrenes, which exhibits excellent stereospecificity, simple mild conditions, and high functional group tolerance.
Herein, N-2-selective beta-thioalkylation of benzotriazoles with unactivated alkenes and styrenes is reported. The N-2-selective beta-thioalkylation of benzotriazoles is highly stereospecific and works under simple and mild conditions, exhibiting excellent functional group tolerance. The high N-2-selectivity is a consequence of the combination of hydroen bonding and Lewis acid/base activation, which reverses the N-2-position to be favored for alkylation.
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