Synthesis
DOI: 10.1055/a-1709-3426
paper

Chemoselective reduction of tertiary amides by 1,3-diphenyldisiloxane (DPDS)

Travis Hammerstad
1  Chemistry, University of Minnesota, Minneapolis, United States
,
Pooja V. Hegde
2  Medicinal Chemistry, University of Minnesota, Minneapolis, United States
,
Kathleen J. Wang
1  Chemistry, University of Minnesota, Minneapolis, United States
,
3  Medicinal Chemistry, University of Minnesota, Minneapolis, United States
› Author Affiliations

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) has been developed. The reaction conditions are tolerant of a great 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 set up and broad chemoselectivity make this method attractive for organic synthesis. These results further demonstrate the utility of DPDS as a selective reducing agent.



Publication History

Received: 16 October 2021

Accepted after revision: 30 November 2021

Publication Date:
30 November 2021 (online)

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