Recent Advances in the Catalytic Synthesis of Arylsulfonyl Compounds

Abstract

Arylsulfonyl compounds are among the most important compounds in pharmaceutical and medicinal chemistry. Hence, a wide variety of sulfonylation methods have been reported recently. This review summarizes arylsulfonylation methodologies developed in the last 5 years and includes two major categories. The first entails direct arylsulfonylation and the second multicomponent arylsulfonylation. In direct arylsulfonylation, arylsulfonyl reagents react with C−H activated compounds, alkynes, and alkenes through coupling or addition reactions. In multicomponent reactions, arylation reagents and various substrates react with sulfur dioxide surrogates, such as DABSO, Na 2 S 2 O 5 , and K 2 S 2 O 5 . Arylsulfonyl hydrazides, aryl boronic acids, aryl silanes, and aryl halides are the most widely employed arylation reagents that react with sulfur dioxide surrogates to generate an arylsulfonyl source, and ensuing reactions proceed via pathways analogous to those of direct arylsulfonylation.

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

“…We, therefore, decided to compile a selection of relevant reaction platforms to highlight the main strategies to achieve this transformation. [263][264][265][266][267][268] Generally speaking, three mechanistic scenarios for the incorporation of SO 2 into organic molecules can be devised. On the one hand, upon photocatalyst-assisted radical generation, SO 2 acts like a radical trap, thus forming an intermediate sulfonyl radical that is then involved in addition reactions on unsaturated bonds.…”

DABSO as a SO2 gas surrogate in the synthesis of organic structures

“…This can be partially attributed to its gaseous form, notable toxicity and stinky properties that force researchers to use other available SO 2 sources. [5][6][7][8][9][10][11] There is a surge of attention paid to innovative and improved synthetic techniques for introduction of sulfur including functional groups, like sulfones and sulfonamides, in the structure of agrochemicals, medicines, and other organic materials. [12][13][14][15][16][17][18] Thus, the development of convenient and stable SO 2 surrogates is thought to be a key driver in the revitalization of sulfur-based organic synthesis research.…”

Cobalt‐Catalyzed Redox‐Neutral Sulfonylative Coupling from (Hetero)aryl Boronic Acids, Ammonium Salts and Potassium Metabisulfite

“…In response to these limitations, the use of transition-metalcatalyzed sulfonylations have been exploited as milder alternative to sulfones. [13][14][15][16][17][18][19] Boronic acids [20] combination with sulfur dioxide surrogates [21][22][23][24] transformed to a variety of valuable functional sulfones has also proved to be successful in the presence of transition-metal Au(I), [22,25] Pd(II), [26][27][28] and Ru(II), [29] Cu(I) [30][31][32] catalysts (Scheme 1a). The redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids was developed by Willis's group.…”