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...

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Bibliographic Details
Published in:Organic letters 2023-02, Vol.25 (5), p.766-770
Main Authors: Fujie, Masaki, Mizufune, Kyohei, Nishimoto, Yoshihiro, Yasuda, Makoto
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c04235