Synthesis 2022; 54(09): 2205-2212
DOI: 10.1055/a-1709-3426
paper

Chemoselective Reduction of Tertiary Amides by 1,3-Diphenyl­disiloxane (DPDS)

Travis A. Hammerstad
a   Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, USA
,
Pooja V. Hegde
b   Department of Medicinal Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, USA
,
Kathleen J. Wang
a   Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, USA
,
b   Department of Medicinal Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, USA
› Institutsangaben


Abstract

A convenient procedure for the chemoselective reduction of tertiary amides at room temperature in the presence of air and moisture using 1,3-diphenyldisiloxane (DPDS) is developed. The reaction conditions tolerate a significant number of functional groups including esters, nitriles, secondary amides, carbamates, sulfoxides, sulfones, sulfonyl fluorides, halogens, aryl-nitro groups, and arylamines. The conditions reported are the mildest to date and utilize EtOAc, a preferred solvent given its excellent safety profile and lower environmental impact. The ease of setup and broad chemoselectivity make this method attractive for organic synthesis, and the results further demonstrate the utility of DPDS as a selective reducing agent.

Supporting Information



Publikationsverlauf

Eingereicht: 16. Oktober 2021

Angenommen nach Revision: 30. November 2021

Publikationsdatum:
30. November 2021 (online)

© 2021. Thieme. All rights reserved

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