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P(III)‐Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
Author(s) -
Meng Haiwen,
Sun Kunhui,
Xu Zhimin,
Tian Lifang,
Wang Yahui
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100113
Subject(s) - chemistry , isocyanate , electrochemistry , phosphine , nucleophile , hydroxamic acid , phosphine oxide , combinatorial chemistry , organic chemistry , polymer chemistry , electrode , catalysis , polyurethane
An external oxidant‐free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri‐substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N‐based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.