Metal-Free Iodine-Promoted Strategy for the Synthesis of C2,C3-Bissulfenylated Indoles

Abstract

An iodine-mediated synthetic approach has been developed for the synthesis of C2, C3-bissulfenyl indoles from C3 phenylthioindoles. The reaction proceeds via C–S bond cleavage of C3 phenylthioindoles to generate aryl hypoiodothioite intermediates, which subsequently react with another molecule of C3 phenylthioindole to afford the C2, C3-bissulfenylindoles. Furthermore, this methodology exhibits excellent compatibility with a variety of indole substrates, demonstrating broad functional group tolerance.