Photo‐promoted Skeletal Rearrangement of Phosphine–Borane Frustrated Lewis Pairs Involving Cleavage of Unstrained C−C σ‐Bonds

Tatsuyoshi Ito, Nobuharu Iwasawa, Jun Takaya

Angewandte Chemie International Edition · 2020 · 16 citations · 50 references

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Abstract

Abstract 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.

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