Synthesis and thermal reactions of perfluoroalkylsulphonyl substituted ylides

Synthesis of superacidic carbon acid and its derivatives

“…As the first example of such ylide synthesis, Zhu and Chen reported that the reaction of (R f SO 2 ) 2 CH 2 with ArI(OAc) 2 in CH 2 Cl 2 gives the corresponding iodonium ylides 37 in good to excellent isolated yields (Table 4) [52]. The same hypervalent iodine(III) compounds were synthesized by the Hanack's group as well [53]. A c c e p t e d M a n u s c r i p t -16-28).…”

Iodonium ylides in organic synthesis

“…26 The nonsymmetric, cyano[(perfluoroalkyl)sulfonyl]-substituted ylides 18 (Scheme 6) 25 or bis(fluorosulfonyl)(phenyliodonium)methanide, PhIC(SO 2 F) 2 , 35 were prepared from (diacetoxyiodo)benzene and appropriate bis(sulfonyl)methanes as starting materials. Scheme 6.…”

“…The relatively stable dicarbonyl derivatives, PhIC(COR) 2 , [19][20][21][22][23] and the disulfonyl derivatives, PhIC(SO 2 R) 2 , [24][25][26][27] are generally prepared by a reaction of PhI(OAc) 2 with appropriate dicarbonyl compounds or disulfones under basic conditions. In particular, phenyliodonium ylides 2 are obtained by the treatment of malonate esters 1 with (diacetoxyiodo)benzene in dichloromethane in the presence of KOH (Scheme 1).…”

Direct Cyclization of Tertiary Aryl Amines with Iodonium Ylides

“…[2] As alternative reagents to diazo compounds, ap redominant application of these ylide compounds is to generate carbene or carbenoid species under thermal, catalytic, or photochemical conditions. [3] These carbene or carbenoid intermediates can participate in ar ange of useful transformations,s uch as transylidation, [4] inter-o ri ntramolecular cyclization, [3,5] and C À Hi nsertion reactions [3,6] (Figure 1A). Iodonium ylides could also show similar reactivity to that of other ylides,s uch as sulfur and phosphorus ylides, [7] since they have been applied in transformations in which they act as nucleophiles.…”