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Urea-Catalyzed Functionalization of Unactivated C–H Bonds

preprint
submitted on 21.02.2020 and posted on 24.02.2020 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.

History

Email Address of Submitting Author

bwwigman@g.ucla.edu

Institution

University of California, Los Angeles

Country

United States

ORCID For Submitting Author

0000-0003-3689-8281

Declaration of Conflict of Interest

No conflict of interest.

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