posted on 2022-06-02, 18:09authored byYang 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.