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

Travis A. Hammerstad, Pooja V. Hegde, Kathleen J. Wang, Courtney C. Aldrich

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2205-2212
Number of pages8
JournalSynthesis (Germany)
Volume54
Issue number9
DOIs
StatePublished - Jan 26 2022

Bibliographical note

Publisher Copyright:
© 2022 Georg Thieme Verlag. All rights reserved.

Keywords

  • amide reduction
  • chemoselectivity
  • disiloxanes
  • silanol
  • zinc catalysis

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