Direct Oxidative Disulfenylation/Cyclization of 2′‐Hydroxyacetophenones with Thiophenols for the Synthesis of 2,2‐Dithio‐Benzofuran‐3(2H)‐Ones

Abstract

A direct oxidative disulfenylation/cyclization of 2'-hydroxyacetophenones with thiophenols mediated by TBAI/K 2 S 2 O 8 has been successfully developed within this study. The reaction successfully provides an efficient method for the synthesis of functionalized 2,2-dithio-benzofuran-3(2H)-ones, which exhibits readily available starting materials, a broad substrate scope, excellent yields, and large-scale applicability. In a single step, two CÀS bonds and one CÀO bond are simultaneously built on the same sp 3 carbon atom under transitionmetal-free conditions.

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds

“…In 2019, Yu and coworkers reported a TBAI/K 2 S 2 O 8 -mediated synthesis of 2,2-dithio-benzofuran-3(2 H )-ones 22 via the direct oxidative dithiolation and intramolecular cyclization of 2′-hydroxyacetophenones 197 with aryl thiols 43 under transition-metal-free conditions (Scheme 58). 261 This protocol was groundbreaking since it simultaneously constructed two C–S bonds and one C–O bond on the same C(sp 3 ) atom in a single operation. It accommodated a variety of differently substituted 2′-hydroxyacetophenones and aryl thiols, including furan-2-ylmethanethiol and 4-mercaptophenol.…”

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

“…This protocol was also successfully applied in the synthesis of tetraaryl methane from triaryl methanol and heteroarenes such as indole and furan. In 2018, the Yan and Yu group reported an oxidative disulfenylation/cyclization reaction of 2 -hydroxyacetophenones with thiophenols mediated by TBAI/K 2 S 2 O 8 for the synthesis of functionalized 2,2-dithio-benzofuran-3(2H)-ones (Scheme 18) [37]. This protocol was featured by metal-free condition, satisfying yields and broad substrate scope.…”