American Chemical Society
cs2c00614_si_001.pdf (3.5 MB)

(CAAC)Copper Catalysis Enables Regioselective Three-Component Carboboration of Terminal Alkynes

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journal contribution
posted on 2022-06-02, 18:09 authored by Yang Gao, Nana Kim, Skyler D. Mendoza, Sima Yazdani, Andre Faria Vieira, Mingyu Liu, Aaron Kendrick, Douglas B. Grotjahn, Guy Bertrand, Rodolphe Jazzar, Keary M. Engle
Cyclic­(alkyl)­(amino)­carbene (CAAC) ligands are found to perturb regioselectivity of the copper-catalyzed carboboration of terminal alkynes, favoring the less commonly observed internal alkenylboron regiosomer through an α-selective borylcupration step. A variety of carbon electrophiles participate in the reaction, including allyl alcohol derivatives and alkyl halides. The method provides a straightforward and selective route to versatile trisubstituted alkenylboron compounds that are otherwise challenging to access.