1-Fluoro-1-sulfonyloxylation of Alkenes by Sterically and Electronically Tuned Hypervalent Iodine: Regression Analysis toward 1,1-Heterodifunctionalization

In the heterodifunctionalization of alkenes, 1,1-regioselectivity remains elusive in sharp contrast to 1,2-regioselectivity. Herein, the 1-fluoro-1-sulfonyloxylation of styrenes with Bu4NBF4 and sulfonic acids using a hypervalent iodine ArI(OAc)2 is reported. Regression analysis of substituents on ArI(OAc)2 suggested that their electron-withdrawing ability and steric factor influence the 1,1-heterodifunctionalization. We designed o-{2,4-(CF3)2C6H3}-and p-NO2-substituted ArI(OAc)2 by the regression analysis to achieve high selectivity.