Regioselective Synthetic Approach to Higher Alkenes from Lower Alkenes with Sulfoxides in the Fe/HO System Direct Alkylation or Arylation of the Csp-H Bond on the C═C Bond of Alkenes.

The regioselective synthetic approach to higher alkenes from lower alkenes by using sulfoxides as alkyl or aryl reagents in the Fe/HO system has been developed. This reaction realized direct alkylation or arylation of alkenes. In this reaction, sulfoxides afforded one Csp or Csp atom to the C═C bond of alkenes; one new Csp-Csp bond or Csp-Csp bond was formed. Nearly 40 products including di-, tri-, and tetra-substituted products were regioselectively synthesized. Both aliphatic and aromatic alkenes could participate in this reaction. Moreover, not only dimethyl sulfoxide but also three other sulfoxides can be applied to this reaction, including diethyl, dibenzyl, and diphenyl sulfoxide. The mechanism studies showed that this reaction may experience a coupling process radical addition-elimination and the Fe/HO system made the sulfoxides offered one alkyl or aryl radical to the C═C bond of alkenes.