SYNTHESIS Best Paper Award 2020: A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols
M. Kanai, K. Oisaki and K. Sakai talk about their award-winning paper on a new bond-weakening borinate catalyst.
The award-winning papers describes the use of a new bond-weakening borinate catalyst that improves the scope of the photoredox α-C–H alkylation of alcohols. Professor Motomu Kanai, Dr. Kounosuke Oisaki and Mr. Kentaro Sakai from The University of Tokyo (Japan) discuss some of the difficulties with known photoredox catalysis/hydrogen atom transfer catalysis (PC-HAT) systems regarding site-selectivity.
In their current study, they conducted DFT-guided screenings of bond-weakening catalysts, which lowered the bond-dissociation energy of alcoholic α-C(sp3)–H bonds via selective recognition. A novel electron-deficient borinate catalyst combined with a PC-HAT system was identified. The ternary hybrid catalysis promoted the α-alkylation of alcohols containing various functional groups and innately weaker C–H bonds covering a large substrate scope from simple primary and secondary alcohols to more complex serine derivatives and a homoserine-containing dipeptide.