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Deaminative Functionalization of Primary Sulfonamides
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Abstract
This chapter presents step by step procedure for deaminative functionalization of primary sulfonamides. The procedures in organic syntheses are intended for use only by persons with proper training in experimental organic chemistry. Sulfonamides and related sulfonyl compounds are pervasive in drug discovery and development. Yet, no methods existed for the mild, late‐stage transformation of sulfonamides to other valuable pharmacophores. The reactions occur under mildly basic conditions in the presence of an NHC catalyst, and benzaldehyde acts as the terminal reductant, forming benzonitrile as the stoichiometric by product. The sulfinate esters that are formed as the immediate products can be derivatized in the same reaction vessel to sulfones, other sulfonamides, sulfonic acids, as well as non‐sulfur containing products through radical desulfonylation or Pd‐catalyzed desulfonylative cross‐coupling.
Title: Deaminative Functionalization of Primary Sulfonamides
Description:
Abstract
This chapter presents step by step procedure for deaminative functionalization of primary sulfonamides.
The procedures in organic syntheses are intended for use only by persons with proper training in experimental organic chemistry.
Sulfonamides and related sulfonyl compounds are pervasive in drug discovery and development.
Yet, no methods existed for the mild, late‐stage transformation of sulfonamides to other valuable pharmacophores.
The reactions occur under mildly basic conditions in the presence of an NHC catalyst, and benzaldehyde acts as the terminal reductant, forming benzonitrile as the stoichiometric by product.
The sulfinate esters that are formed as the immediate products can be derivatized in the same reaction vessel to sulfones, other sulfonamides, sulfonic acids, as well as non‐sulfur containing products through radical desulfonylation or Pd‐catalyzed desulfonylative cross‐coupling.
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