Yingying Meng, Ming Wang, Xuefeng Jiang
Oct 31, 2019
Citations
0
Influential Citations
99
Citations
Quality indicators
Journal
Angewandte Chemie
Abstract
Sulfone motifs have attracted considerable interest due to their extensive applications in pharmaceuticals and organic photoconducting materials. Conventionally, sulfones are prepared via the oxidation of sulfides with strong oxidants, which has low functional group compatibility. Herein, a multicomponent reductive cross-coupling involving an inorganic salt ( sodium metabisulfite) for the straightforward construction of sulfones is disclosed. Both intramolecular and intermolecular reductive cross-couplings were comprehensively explored, and diverse sulfones were accessible from the corresponding alkyl and aryl halide s. Intramolecular cyclic sulfones were systematically obtained from five- to twelve-membered rings . Naturally occurring aliphatic systems , such as steroids, saccharides and amino acids, were highly compatible with the SO 2 -insertion reductive cross-coupling . Four clinically applied drug molecules, which include multiple heteroatoms and functional groups with active hydrogens, were successfully prepared via a late-stage SO 2 insertion. Mechanistic studies demonstrated that alkyl radicals and sulfonyl radicals were both involved as intermediates in this transformation.