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 Bu 4 NBF 4 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-(CF 3 ) 2 C 6 H 3 }- and p -NO 2 -substituted ArI(OAc) 2 by the regression analysis to achieve high selectivity.