Metal- and Base-Free C(sp2)-H Arylsulfonylation of Enamides for Synthesis of (E)-β-Amidovinyl Sulfones via the Insertion of Sulfur Dioxide.

Organic Letters
Lei ChenZhong Lian

Abstract

A metal- and base-free C(sp2)-H direct arylsulfonylation of secondary and tertiary enamides with aryldiazonium salts and ex situ generated SO2 (from SOgen) is presented. This method runs smoothly to produce β-amidovinyl sulfones with excellent stereoselectivities in moderate to excellent yields. Moreover, this strategy features good functional group tolerance and environmentally benign reaction conditions. Mechanistic experiments indicate that this sulfonylation may proceed in a radical pathway.

References

Oct 30, 2010·Journal of the American Chemical Society·Bao NguyenMichael C Willis
Dec 7, 2010·Bioorganic & Medicinal Chemistry Letters·Micheal NottinghamJohn D Buynak
Jan 10, 2018·Chemistry : a European Journal·Kamil HofmanGeorg Manolikakes
May 21, 2019·Organic & Biomolecular Chemistry·Philipp KramerGeorg Manolikakes
Jan 24, 2020·Organic & Biomolecular Chemistry·Tonghao ZhuJie Wu

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