Direct C-H Methylsulfonylation of Alkenes with the Insertion of Sulfur Dioxide

Fu-Sheng He; Xinxing Gong; Pornchai Rojsitthisak; Jie Wu

doi:10.1021/acs.joc.9b01729

Direct C-H Methylsulfonylation of Alkenes with the Insertion of Sulfur Dioxide

J Org Chem. 2019 Oct 18;84(20):13159-13163. doi: 10.1021/acs.joc.9b01729. Epub 2019 Sep 12.

Authors

Fu-Sheng He¹, Xinxing Gong², Pornchai Rojsitthisak³, Jie Wu^{1

2

4}

Affiliations

¹ School of Pharmaceutical and Materials Engineering and Institute for Advanced Studies , Taizhou University , 1139 Shifu Avenue , Taizhou 318000 , China.
² Department of Chemistry , Fudan University , 2005 Songhu Road , Shanghai 200438 , China.
³ Department of Food and Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences , Chulalongkorn University , 254 Phayathai Road, Patumwan , Bangkok 10330 , Thailand.
⁴ State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

PMID: 31512476
DOI: 10.1021/acs.joc.9b01729

Abstract

The direct C-H methylsulfonylation of alkenes using inorganic sodium metabisulfite as the sulfur dioxide surrogate is described. This method provides convenient access to (E)-2-methyl styrenyl sulfones in good yields. In general, the in situ generated methyl radical from di-tert-butyl peroxide undergoes a methylsulfonylation process with the combination of sulfur dioxide.