Direct Synthesis of N,N-Disubstituted Formamides by Oxidation of Imines Using an HFIP/UHP System

Natalia Llopis, Patricia Gisbert and Alejandro Baeza*

*Departamento de Quı́mica Orgánica and Instituto de Sı́ntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante. Apdo. 99, E-03080 Alicante, Spain, Email: alex.baezaua.es

N. Llopis, P. Gisbert, A. Baeza, J. Org. Chem., 2020, 85, 11072-11079.

DOI: 10.1021/acs.joc.0c01579

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Abstract

A combination of 1,1,1,3,3,3-hexafluoroispropanol (HFIP) and H₂O₂ enables a straightforward synthesis of N,N-disubstituted formamides from imines in very good yields via an oxidation-rearrangement sequence under smooth reaction conditions.

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proposed mechanism

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Key Words

oxidation, N-substitution, UHP

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ID: J42-Y2020