ol2c03170_si_001.pdf (4.53 MB)
Formal Hydrotrimethylsilylation of Styrenes with Anti-Markovnikov Selectivity Using Hexamethyldisilane
journal contribution
posted on 2022-11-24, 20:05 authored by Xin Wang, Zhi-Xiang Yu, Wen-Bo LiuA combination
of CsF and hexamethyldisilane in DMSO enabling an
anti-Markovnikov formal hydrotrimethylsilylation of styrenes is reported.
Mechanistic investigations detail the reaction pathways, including
in situ generation of a silyl anion, the addition of this silyl anion
onto the alkene to form a carbanion, and this carbanion is then protonated
by DMSO. The choice of the solvent to match its reactivity with the
carbanion and silyl anion is key to the success of this reaction.