posted on 2023-12-28, 15:46authored byJu Hyun Youn, Su Yong Go, Hyunho Chung, Haeyeon Lee, Taek Dong Chung, Paul Ha-Yeon Cheong, Hong Geun Lee
A practical
method for C(sp3)–B bond activation
was developed. Using a combination of alkyl trifluoroborates and N-iodosuccinimide (NIS), various C(sp3)–heteroatom
bonds were readily generated in an efficient manner. Mechanistic studies
revealed the bifunctional ability of NIS: mediating the formation
of reactive halogenated intermediates and activating them via halogen
bonding. This electrophilic activation of the reaction center enables
the utilization of general heteroatom nucleophiles, which are used
in a limited capacity in traditional 1,2-metalate rearrangements.