Aryl fluorosulfates: powerful and versatile partners in cross-coupling reactions

Abstract

Aryl fluorosulfates are versatile building blocks in organic synthesis and have gained increasing attention in SuFEx (Sulfur Fluoride Exchange) click chemistry.

Recent progress in reductive carboxylation of C–O bonds with CO2

“…Fluorosulfates (OFs) as a more stable and eco-friendly alternative of triflates, have recently gained increasing attention as versatile electrophilic partners in cross-coupling reactions. 36 They are easily and conveniently prepared from alcohols using sulfuryl fluoride (SO 2 F 2 ) as an inexpensive sulfonyl fluoride provider.…”

Photocatalytic iodosulfonylation of internal alkynes under green conditions

“…Methods for creating carbon-heteroatom bonds, including C-S bonds, are in high demand in modern organic chemistry. [1][2][3][4][5][6][7][8][9][10] Sulfur-containing compounds are widely used as catalysts, 11,12 reagents and synthetic intermediates, [13][14][15][16][17][18][19] as well as for the preparation of biologically active compounds 20 and functional materials. 21,22 One important class of organosulfur compounds are sulfones, especially vinyl sulfones (Scheme 1).…”

“…Methods for creating carbon–heteroatom bonds, including C–S bonds, are in high demand in modern organic chemistry. 1–10 Sulfur-containing compounds are widely used as catalysts, 11,12 reagents and synthetic intermediates, 13–19 as well as for the preparation of biologically active compounds 20 and functional materials. 21,22…”

Isolation and Reactivity of Arylnickel(II) Complexes in Nickel-Catalyzed Borylation of Aryl Fluorosulfates

“…Aryl fluorosulfates show excellent stability against hydrolysis and thermolysis when compared to sulfonyl halides . These advantages of aryl fluorosulfates have enabled their exploration as a convenient source of electrophiles within catalytic reactions. − However, there is a lack of experimental characterization of well-defined nickel complexes within catalytic cycles. Herein, we present an efficient deoxygenative borylation of aryl fluorosulfates under mild conditions, achieved through nickel-catalyzed C–O bond activation instead of the typical S–F bond cleavage in SuFEx chemistry.…”