Chemoselective one-pot synthesis of β-keto sulfones from ketones

Abstract

A practical method to synthesize substituted b-keto sulfones directly from ketones at room temperature has been developed. This method involves the nucleophilic addition of a base generated enolate to sulfonyl iodide. The reaction shows high chemoselectivity for the addition of a sulfonyl group to an a-carbon over a hydroxyl group. In addition, the given protocol provides good to excellent yields of b-keto sulfones under mild reaction conditions. Moreover, the regiochemical aspect of the protocol is also explored.

Aerobic α‐Sulfonylation of Ketones with Zinc Sulfinates in Aqueous Micellar Media: Highly Selective Access to β‐Keto Sulfones

“…Later in 2014, Sreedhar et al. disclosed a convenient procedure for syntheses of β‐keto sulfones via nucleophilic addition of the in situ generated enolates to sulfonyl iodides . Shortly afterwards, a mild CuBr 2 /DBU catalyzed cross‐coupling reactions between aryl ketones and sodium sulfinates at room temperature was reported .…”

“…Later in 2014, Sreedhar et al disclosed a convenient procedure for syntheses of β-keto sulfones via nucleophilic addition of the in situ generated enolates to sulfonyl iodides. [17] Shortly afterwards, a mild CuBr 2 /DBU catalyzed cross-coupling reactions between aryl ketones and sodium sulfinates at room temperature was reported. [18] Most recently, Tang group described a convenient oxidative sulfonylation of aryl ketones employing sodium sulfinates as the sulfone source and DMSO as the oxidant.…”

Cu-doped zeolitic imidazolate framework catalysed highly selective conversion of alkynes to $$\upbeta $$ β -keto and vinyl sulfones using sodium sulfinates

“…19 Over the years, a number of procedures were made available for the preparation of vinyl and β-keto sulfones. [20][21][22][23][24][25][26][27][28] However, the major drawbacks of some of these methods include longer reaction periods, high temperatures and the formation of side products. Hence, the development of a new protocol for the synthesis of vinyl and β-keto sulfones using reusable heterogeneous catalyst is highly beneficial.…”

Novel 4‐Heteroaryl‐antipyrines: Synthesis, Molecular Docking, and Evaluation as Potential Anti‐breast Cancer Agents

“…Sulfone derivatives have attracted considerable attention due to their broad spectrum of biological activities and their great importance in organic chemistry . Among the derivatives of sulfones, special attention has been drawn to the construction and reactivity of β‐keto sulfones . Some β‐keto sulfones have been reported as effective antimicrobial agents .…”