Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis

Abstract

Sulfones are common, readily available reagents that have recently attracted attention as versatile reagents for cross-coupling reactions. This Review summarizes advances in desulfonylative transformations of sulfones affected by molecular catalysis, including transition-metal catalysts, photocatalysts, and organocatalysts. In addition to catalyst choice, the design of the sulfonyl group is a critical factor to control reactivity. The concepts presented herein will provide new strategies to construct diverse molecules with high efficiency and modularity.

Ni-catalyzed C–S bond construction and cleavage

“…Since Wenkert's group first realized nickel-catalyzed C-S bond cleavage of sulfones in 1979, 89 this strategy has been widely explored and applied. 90 In 2012, Li's research group developed the cross-coupling of Ts-alkanes and Grignard reagents by means of Kumada coupling (Scheme 55). 91 A series of alkenes and aryl ketones were successfully synthesized using this strategy.…”

Designing Photothermal Superhydrophobic PET Fabrics via In Situ Polymerization and 1,4-Conjugation Addition Reaction

“…Solar energy is considered to be a clean and renewable energy source and can be utilized through photocatalysis, − photothermal conversion, − photovoltaic, − and so on. Among them, photothermal conversion technology is the most direct application of solar energy.…”

Desulfonylative Coupling of Alkylsulfones with gem-Difluoroalkenes by Visible-Light Photoredox Catalysis

“…Building on the work of our group and others with regards to the application of sulfones in catalysis, − we show that visible-light photoredox catalysts − can be employed to promote the reductive desulfonylation of tertiary alkylsulfones and their reaction with gem -difluoroalkenes (Scheme c). Previous reports from our group, the Sengoku/Yoda group, and the Chatterjee group have shown that carbon radicals can be generated from alkylsulfones either through single electron reduction promoted by Zn and 1,10-phenanthroline (phen) or visible-light-induced reduction.…”