A Practical, One-Pot Synthesis of Sulfonylated Pyridines

Abstract

A concise and efficient one-pot synthesis of functionalized sulfonylated pyridines via an S(N)Ar reaction of readily available pyridines and sodium sulfinate salts in the presence of tetrabutylammonium chloride is presented.

Transition‐Metal‐Free Approaches to Arylsulfones using Benzylic Ammonium Salts through C−N Bond Cleavage

“…On the basis of these results and previous works, this reaction may occurs through S N mechanism instead of TM catalysis or a radical process in the presence of suitable base or additive, and the corresponding aryl alkyl sulfone were afforded releasing a molecule of trimethylamine simultaneously . More detailed mechanistic studies of this reaction are ongoing in our laboratory.…”

Transition Metal‐Free Difunctionalization of C−C Bond with Sodium Sulfinates and Water Leading to (E)‐1‐Phenyl‐4‐sulfonylbut‐1‐enes

“…Sodium sulfinates, as readily accessible salts with high activity, are widely used in organic synthesis and pharmaceutical chemistry. [11][12][13][14][15][16] Therefore, a series of interesting transformations were developed by using sodium sulfinates as the sulfonyl source or alkyl source (usually aryl groups were afforded by desulfinylation). [11] Recently, many chemists have reported sulfonylation methods for cross-coupling reactions and difunctionalization reactions by utilizing sodium sulfinates as the sulfonyl source.…”

“…[11] Recently, many chemists have reported sulfonylation methods for cross-coupling reactions and difunctionalization reactions by utilizing sodium sulfinates as the sulfonyl source. For couplings with CÀX, [12] a variety of CÀX species, such as C-halogen, CÀN 2 BF 4 , CÀOTf, CÀCOOH and CÀB(OH) 2 , have been utilized. In 2011, Maloney and co-workers [12a] reportedthe cross-coupling reaction between chloropyridines and sodium sulfinates for accessing sulfonylated pyridine moieties.…”

Sulfonylation of Benzylic C−H Bonds through the Reaction of Aryl(o‐tolyl)methanones with Sulfonyl Hydrazides or Sulfonyl Chlorides

“…However,t his method was limited, owing to the unpleasant smell of thiols and the incompatibility of sensitive functional groups under oxidative conditions. Recently,s ulfonylation reactions have been achievedm uch more conveniently from ar ange of sulfonyl precursors, such as sulfonyl hydrazides, [5] sulfonyl chlorides, [6] sulfinic acids, [7] sodium sulfonates, [8] and sulfur-dioxide surrogates. [9] Sulfonyl radicals can be generated from these precursors in the presence of am etal catalysto ru nder metal-free conditions, and this strategy has been found to be an efficient method for the generation of diverses ulfones or sulfonyl compounds.…”