TBAI-mediated regioselective sulfenylation of indoles with sulfonyl chlorides in one pot

Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters

“…Meanwhile, a reduced sulfide intermediate was obtained through a reduction of sulfonyl chloride. Here, the reduction of sulfonyl chloride could be mediated by Mo­(CO) 6 or promoted by ZnI 2 and H 2 O . Subsequently, a nucleophilic attack of the sulfide with an acylnickel complex gives the thioesters.…”

“…A plausible reaction mechanism was proposed based on the above results and literature (Scheme ). − First, a ligated Ni II Ln complex was formed in the presence of ligand and nickel precursors. Then, under the assistance of K 2 CO 3 , a transmetalation of phenylboronic acid with Ni II Ln provided intermediate A , which transferred to acylnickel complex B via a coordination and insertion of CO from Mo­(CO) 6 .…”

Sulfenylation of Indoles Mediated by Iodine and Its Compounds

“…Sulfenylation of indole 36 with sulfonyl chlorides 37 was also performed under the action of the TBAI/HBr system in PEG 400 at 50 °C (Scheme 19). [65] Later, such transformation was also realized with TBAI in DMF at 60 °C [66] and at 120 °C in the case of azaindole sulfenylation [67] . TBAI‐mediated sulfenylation of indole with sulfonyl hydrazides was also performed in DPDME at 100 °C [68] .…”

Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides

“…As bench-stable and readily accessible reagents, sodium sulfinates have recently emerged as promising starting materials to form a C–S bond via sulfenylation transformations . Recently, the Li and Zhou group has reported sulfenylation of imidazo­[1,2- a ]­pyridine with sodium sulfinates as the sulfur sources (Scheme d) .…”