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P(III)‐Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
Ist Teil von
European journal of organic chemistry, 2021-03, Vol.2021 (11), p.1768-1772
Ort / Verlag
Weinheim: Wiley Subscription Services, Inc
Erscheinungsjahr
2021
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
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.
P(III)‐assisted electrochemical generation of isocyanates from hydroxamic acids was successfully applied in the synthesis of ureas. Hydroxamic acids were directly used without pre‐activation, and the reaction was found not sensitive to water or air. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with trivalent phosphine to form corresponding alkoxyphosphoniums, and subsequent rearrangement to give isocyanates.