Nano copper catalyzed synthesis of symmetrical/unsymmetrical sulfones from aryl/alkyl halides and p-toluenesulfonylmethylisocyanide: TosMIC as a tosyl source

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

“…This result indicates that TosMIC may decompose to a Ts anion and formaldehyde, possibly accompanied by the formation of a cyanide ion [ 54 ]. The previous reports on the reaction mechanism of TosMIC as a source of Ts are mainly a radical mechanism [ 19 – 23 ]. To assess the possibility of radical intermediates, a stoichiometric amount of the radical inhibitor 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) was subjected to the model reaction system, however, the reaction was not inhibited ( Scheme 6B ).…”

“…In general, TosMIC undergoes base-mediated 1,3-dipolar cycloadditions with activated alkenes to provide pyrroles as products [ 18 ] ( Scheme 1A ). Recently, alternative functionalizations using TosMIC as a tosyl source of arylalkenes or alkynes provided an attractive option for the synthesis of vinyl sulfones [ 19 – 23 ] ( Scheme 1B ). However, in contrast to the reaction of TosMIC as tosyl source with various aryl olefins, reports relating to reactions of TosMIC with electron-deficient olefins such as p -QMs for the preparation of highly valuable diarylmethyl sulfones are relatively scarce [ 24 ].…”

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

“…Cyclization strategies [35][36][37][38][39][40][41][42][43][44][45] as well as cycloaddition/cyclocondensation techniques [46][47][48][49][50][51] represent those with heteroring construction. Alternative approaches rely on a peripheral modification of various substrates, such as 3-bromoquinolines [52][53][54][55], quinoline-3-boronic acids [56], and diazonium salts [57].…”