A Practical and General Amidation Method from Isocyanates Enabled by Flow Technology

Angewandte Chemie
Jason D WilliamsDavid M Lindsay

Abstract

The addition of carbon nucleophiles to isocyanates represents a conceptually flexible and efficient approach to the preparation of amides. This general synthetic strategy has, however, been relatively underutilized owing to narrow substrate tolerance and the requirement for less favourable reaction conditions. Herein, we disclose a high-yielding, mass-efficient, and scalable method with appreciable functional group tolerance for the formation of amides by reaction of Grignard reagents with isocyanates. Through the application of flow chemistry and the use of substoichiometric amounts of CuBr2 , this process has been developed to encompass a broad range of substrates, including reactants found to be incompatible with previously published procedures.

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Oct 27, 2018·Organic & Biomolecular Chemistry·Karen de la Vega-HernándezVittorio Pace
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Jun 18, 2021·Beilstein Journal of Organic Chemistry·Guido GambacortaIan R Baxendale
Dec 12, 2019·Journal of the American Chemical Society·Daniele FioritoClément Mazet
Jan 12, 2022·ChemSusChem·Antonella Lenia AlfanoMargherita Brindisi

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