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Catalytic asymmetric C–H insertion reactions of vinyl carbocations

https://doi.org/10.1126/science.ade5320

Nistanaki, Sepand K.; Williams, Chloe G.; Wigman, Benjamin; Wong, Jonathan J.; Haas, Brittany C.; Popov, Stasik; Werth, Jacob; Sigman, Matthew S.; Houk, K. N.; Nelson, Hosea M. (December 2022, Science)

Organocatalysts impart enantiocontrol over dicoordinated vinyl carbocations in C(sp3) –H functionalization reactions.
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Ligand-Accelerated Catalysis in Scandium(III)-Catalyzed Asymmetric Spiroannulation Reactions

https://doi.org/10.1021/acscatal.1c05768

Ball-Jones, Nicolas R.; Cobo, Angel A.; Armstrong, Brittany M.; Wigman, Benjamin; Fettinger, James C.; Hein, Jason E.; Franz, Annaliese K. (March 2022, ACS Catalysis)

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Vinyl Carbocations Generated under Basic Conditions and Their Intramolecular C–H Insertion Reactions

https://doi.org/10.1021/jacs.9b02110

Wigman, Benjamin; Popov, Stasik; Bagdasarian, Alex L.; Shao, Brian; Benton, Tyler R.; Williams, Chloé G.; Fisher, Steven P.; Lavallo, Vincent; Houk, K. N.; Nelson, Hosea M. (May 2019, Journal of the American Chemical Society)

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Electrochemical Fluorination of Vinyl Boronates through Donor‐Stabilized Vinyl Carbocation Intermediates**

https://doi.org/10.1002/anie.202113972

Wigman, Benjamin; Lee, Woojin; Wei, Wenjing; Houk, Kendall N.; Nelson, Hosea M. (February 2022, Angewandte Chemie International Edition)

Abstract The electrochemical generation of vinyl carbocations from alkenyl boronic esters and boronates is reported. Using easy‐to‐handle nucleophilic fluoride reagents, these intermediates are trapped to form fully substituted vinyl fluorides. Mechanistic studies support the formation of dicoordinated carbocations through sequential single‐electron oxidation events. Notably, this electrochemical fluorination features fast reaction times and Lewis acid‐free conditions. This transformation provides a complementary method to access vinyl fluorides with simple fluoride salts such as TBAF.
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