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Strong Bases and Weak Anions in Catalytic C–H Insertion Reactions of Vinyl Carbocations

preprint
submitted on 12.12.2018 and posted on 12.12.2018 by Benjamin Wigman, Stasik Popov, Alex L. Bagdasarian, Brian Shao, Tyler R. Benton, Chloé G. Williams, Steven P. Fisher, Vincent LaVallo, Kendall N. Houk, Hosea Nelson

Here we report the surprising discovery that high-energy vinyl carbocations can be generated under strongly basic conditions, and that they engage in intramolecular sp3 C–H insertion reactions through the catalysis of commercially available weakly coordinating anion salts. This approach relies on the unconventional combination of lithium hexamethyldisilazide base and the commercially available catalyst, triphenylmethylium tetrakis(pentafluorophenyl)borate. These reagents form a catalytically active lithium species that enables the application of vinyl cation C–H insertion reactions to heteroatomcontaining substrates.

Funding

R35 GM128936

History

Email Address of Submitting Author

hosea@chem.ucla.edu

Institution

UCLA

Country

USA

ORCID For Submitting Author

0000-0002-4666-2793

Declaration of Conflict of Interest

no conflict of interest

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