Efficient silver-catalyzed direct sulfenylation and selenylation of rich arenes

Abstract

An efficient protocol for silver/copper-cocatalyzed direct sulfenylation and selenylation of arenes with aryl disulfides and diselenides has been developed. This strategy exhibits excellent functional group tolerance and high regioselectivity. Mono sulfenylation and selenylation products can be exclusively achieved. This reaction provides a simple and practical route to the preparation of aryl sulfides and selenides.

Triphenyltin recognition by primary structures of effector proteins and the protein network of Bacillus thuringiensis during the triphenyltin degradation process

“…1b. It is deduced that the tin atom in TPT bound to some AAs of ribosome-associated factor Y and provided more binding sites for Ag + in the solution condition because Ag + can bind to benzene rings in TPT 14 . Tin atoms and benzene rings in TPT bound to different AAs of the protein during electrophoresis, resulting in protein folding and a subsequent decrease in Ag + binding sites.…”

Iodine(III) Enabled Dehydrogenative Aryl C−S Coupling by in situ Generated Sulfenium Ion

“…(4‐Chlorophenyl)(mesityl)sulfane (3 ac) : R f =0.85 (Hexane); white solid; yield 87% (95 mg); mp 78–80 °C (lit . 74–75 °C); 1 H NMR (400 MHz, CDCl 3 ) δ 7.14 (d, J =8.6 Hz, 2H), 7.02 (s, 2H), 6.84 (d, J =8.6 Hz, 2H), 2.38 (s, 6H), 2.33 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.8, 139.7, 137.2, 130.4, 129.6, 129.1, 126.8, 126.7, 21.8, 21.3.…”

“…(4-Bromophenyl)(mesityl)sulfane (3 aa): [3] R f = 0.85 (Hexane); off white solid; yield 96% (94 mg); mp 96-100 8C; 1 Mesityl(phenyl)sulfane (3 ab): [3] R f = 0.9 (Hexane); Colourless liquid; yield 97% (120 mg); 1 H NMR (400 MHz, CDCl 3 ) (4-Chlorophenyl)(mesityl)sulfane (3 ac): [42] R f = 0.85 (Hexane); white solid; yield 87% (95 mg); mp 78-80 8C (lit. [7b]…”

Heterogeneously Catalyzed Direct CH Thiolation of Heteroarenes

“…[7] Cu, Rh, and Ru catalysts have also proven to be successful at promoting this transformation. [9] Indeed, only few examples of non-directed C À Ht hiolation exist in the literature and they usually require very specific sulfenylating agents that are not commercially available.I n 2001, Kita and co-workers reported the first sulfenylation of electron-rich (hetero)arenes through the use of aq uinonederived thiolation reagent ( Figure 2). [9] Indeed, only few examples of non-directed C À Ht hiolation exist in the literature and they usually require very specific sulfenylating agents that are not commercially available.I n 2001, Kita and co-workers reported the first sulfenylation of electron-rich (hetero)arenes through the use of aq uinonederived thiolation reagent ( Figure 2).…”

“…[5t] Nevertheless, ad irecting group free [8] general method for the direct CÀH functionalization of electron-rich heteroarenes,s uch as thiophene,b enzo[b]thiophene,o rb enzofuran, remains elusive. [9] Indeed, only few examples of non-directed C À Ht hiolation exist in the literature and they usually require very specific sulfenylating agents that are not commercially available.I n 2001, Kita and co-workers reported the first sulfenylation of electron-rich (hetero)arenes through the use of aq uinonederived thiolation reagent ( Figure 2). [10] In 2011, Yamaguchi and co-workers reported arhodium-catalyzed CÀHthiolation of heteroaromatic compounds that makes use of a-(phenylthio)ketones as the thiol source,h owever, only single examples of an electron-poor benzo[b]thiophene and thiophene were described.…”