Regiocontrolled carbonylsulfanylations at ortho-position of phenols and at α-position of ketones using chlorocarbonylsulfenyl chloride

Article abstract of DOI:10.3987/com-98-s(h)23

Bu₃N/AlCl₃-promoted [3+2] cyclocondensation between phenols and chlorocarbonylsulfenyl chloride (CCSC; 3) gave 1,3-benzoxathiol-2-ones (2), wherein the acylation of phenols with CCSC (3) and the intramolecular and regioselective ortho-sulfenylation successively proceeded in a one-pot manner. 2-Sulfanylphenols (1) were produced from 2 by mild hydrolysis using NaOH. An analogous Bu3N-promoted [3+2] cyclocondensation between ketones and 3 gave 1,3-oxathioles (7), wherein the α-CH₂- position of the ketones was regioselectively sulfenylated.