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Photo‐promoted Skeletal Rearrangement of Phosphine–Borane Frustrated Lewis Pairs Involving Cleavage of Unstrained C−C σ‐Bonds
Author(s) -
Ito Tatsuyoshi,
Iwasawa Nobuharu,
Takaya Jun
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004444
Subject(s) - borane , frustrated lewis pair , phosphine , chemistry , phosphonium , cleavage (geology) , bond cleavage , rearrangement reaction , photochemistry , lewis acids and bases , medicinal chemistry , catalysis , polymer chemistry , organic chemistry , materials science , fracture (geology) , composite material
An unprecedented photo‐promoted skeletal rearrangement reaction of phosphine–borane frustrated Lewis pairs, o‐(borylaryl)phosphines, involving cleavage of an unstrained sp 2 C–sp 3 C σ‐bond is reported. The reaction realizes an efficient synthesis of cyclic phosphonium borate compounds. The reaction mechanism via a boranorcaradiene intermediate is proposed based on theoretical calculations. This work sheds light on the new photoreactivity of phosphine–borane FLPs.