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May 2, 20263 citations

Deoxycyanation of Alkyl Alcohols Using Photoredox Catalysis.

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CHCarla HümpelWLWilliam L. LyonRMRyan E. McNamee

Key Points

  • The aim is to develop a safer method for synthesizing alkyl nitriles through deoxycyanation of alkyl alcohols.
  • Photoredox-catalyzed reaction
  • Metal-free approach
  • Utilization of tosyl cyanide as a reagent
  • Successfully synthesized a variety of 1°, 2°, and 3° cyanides
  • Achieved rapid reaction times
  • Minimized use of toxic cyanide sources

Abstract

Cyano groups represent an important class of functional motifs in medicinal chemistry given their synthetic versatility and capacity to engage in essential interactions with biological targets. However, the synthesis of sterically hindered alkyl nitriles remains challenging, and, furthermore, traditional methods often rely on toxic cyanide sources. Herein, we report a photoredox-catalyzed, metal-free deoxycyanation of alkyl alcohols that allows rapid access to a wide array of 1°, 2°, and 3° cyanides using the easily handled, low-toxicity, tosyl cyanide reagent.

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Cite This Study

Hümpel et al. (2026) studied this question.

synapsesocial.com/papers/69f594ca71405d493afffadehttps://doi.org/10.1021/acs.orglett.6c00711
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