Alkoxyphosphorane/Borane Cooperative Alkylations: A Frustrated Lewis Pair Version of the Mitsunobu Reaction.
Ting ChenYanbo MeiLiu Leo LiuYufen ZhaoYile WuDouglas W StephanPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2023)
The combination of the alkoxyphosphoranes, Ph 2 P(OR)(O 2 C 6 Cl 4 ) and the borane B(C 6 F 5 ) 3 generates the zwitterions 3 which act as FLP to effect the alkylation of several nucleophiles affording C-C, C-N, C-H and C-Cl coupling products. A DFT study shows the reaction proceeds via an FLP activation pathway generating an alkoxyphosphonium intermediate which effects the alkylation of the nucleophiles, akin to the Mitsunobu reaction.