Sulfur Dioxide Insertion Reactions for Organic Synthesis

SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling

“…1 Because it has a high atom-efficiency, the insertion of a sulfur dioxide molecule upon coupling a nucleophile with an electrophile has recently emerged as a valuable route. 5 Organomagnesium, 6 organozinc 7 and organoboron 8 compounds were successively reported as nucleophiles; yet, they suffer from toxicity issues, functional group incompatibility, and/or air-sensitivity. 9 Because they are readily available, air-stable and show an improved functional-group tolerance, organosilanes were recently considered to produce sulfones from SO2 or SO2 surrogates.…”

Trifluoromethylfluorosulfonylation of Unactivated Alkenes Using Readily Available Ag(O2CCF2SO2F) and N‐Fluorobenzenesulfonimide

“…These experimental results suggest that AgCF 3 generated in situ from Ag(O 2 CCF 2 SO 2 F) may be the key CF 3 radical source. Finally, addition of the new alkyl radical, formed by addition of the CF 3 radical to the alkene, to sulfur dioxide, and subsequent reaction with NFSI generate SO 2 F groups in the desired products . It should be mentioned that Reiser et al.…”

Investigating the cheletropic reaction between sulfur dioxide and butadiene-containing linkers in UiO-66

“…As shown in Scheme 1, 1,3-butadiene, and derivatives of 1,3butadiene, have been shown to undergo a cheletropic addition of sulfur dioxide to form a butadiene sulfone (sulfolene). [43][44][45] This cheletropic reaction is known to be reversible under elevated temperature. 43,46,47 Thus, we hypothesized that incorporation of 1,3-butadiene into a highly porous structure may improve the removal of sulfur dioxide.…”