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Urea-Catalyzed Functionalization of Unactivated C–H Bonds

submitted on 21.02.2020, 23:19 and posted on 24.02.2020, 12:22 by Alex L. Bagdasarian, Stasik Popov, Benjamin Wigman, Wenjing Wei, woojin lee, Hosea Nelson
Herein we report the 3,5bistrifluoromethylphenyl urea-catalyzed functionalization of unactivated C–H bonds. In this system, the urea catalyst mediates the formation of high-energy vinyl carbocations that undergo facile C–H insertion and Friedel–Crafts reactions. We introduce a new paradigm for these privileged scaffolds where the combination of hydrogen bonding motifs and strong bases affords highly active Lewis acid catalysts capable of ionizing strong C–O bonds. Despite the highly Lewis acidic nature of these catalysts that enables triflate abstraction from sp2 carbons, these newly found reaction conditions allow for the formation of heterocycles and tolerate highly Lewis basic heteroaromatic substrates. This strategy showcases the potential utility of dicoordinated vinyl carbocations in organic synthesis.


Email Address of Submitting Author


University of California, Los Angeles


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest.


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