Categories: C-S Bond Formation >
Synthesis of sulfinic acids
Decatungstate photocatalysis enables a direct conversion of strong, aliphatic C(sp3)-H bonds into the corresponding alkyl sulfinic acids . This transformation has been applied to a diverse range of C(sp3)-rich scaffolds, including natural products and approved pharmaceuticals, providing efficient access to complex sulfur-containing products.
P. J. Sarver, N. B. Bissonnette, D. W. C. MacMillan, J. Am. Chem. Soc., 2021, 143, 9737-9743.
A Pd-catalyzed coupling of aryl iodides and the sulfur dioxide surrogate DABSO provides aryl ammonium sulfinates, that can be transformed in a one-pot process to various functionalized sulfonamides by simple treatment with an aqueous solution of the relevant amine and sodium hypochlorite (bleach). A broad range of amines, including anilines, and amino acid derivatives can be used.
E. F. Flegeau, J. M. Harrison, M. C. Willis, Synlett, 2016, 27, 101-105.