Ruthenium(II)‐Catalyzed C−H Chalcogenation of Anilides

Abstract

Ruthenium-catalyzed CÀH chalcogenations of anilides with readily available diselenides and disulfides have been achieved. Our strategy features ample substrate scope, affording the mono-ortho selenylated and thiolated anilides with complete site selectivity control and high catalytic efficacy. Detailed mechanistic studies provide strong support for a facile base-assisted internal electrophilic substitution (BIES) metalation event.

Nickel-Catalyzed Regioselective Thiolation of Anilides with Thiols

“…Although the exact mechanism remains unclear, based on the above results and the Ni-mediated C–H thiolation reactions in previous reports, 19a 21 a plausible mechanism for the reaction is shown in Scheme 6 . Under Nickel catalysis, the first step is Ni catalyzed C–H activation via metalation-deprotonation to generate the Ni(II)-intermediate A .…”

Ligand‐Free Palladium(II)‐Catalyzed ortho‐C–H Chalcogenations of N‐Arylsulfonamide via Weak Coordination

“…The chelation‐assisted Pd(II)‐catalyzed C–H chalcogenation of arenes has been successively reported by the Nishihara and Kambegroups. Moreover, we established an efficient ruthenium catalyzed C–H chalcogenation of anilides by weak coordination (Scheme c) . Based on the pioneering work in the transition metal catalyzed C–H chalcogenations, herein, we report the first example of Pd‐catalyzed direct expedient ortho ‐C–H chalcogenations of sulfonamides via weak coordination under mild conditions using readily available diselenides and disulfides, respectively (Scheme d).…”

PIDA‐Promoted Selective C5 C−H Selenylations of Indolines via Weak Interactions

“…Inspired by these reports and our interest on the research of diaryl selenides synthesis, [14] we herein report the first example of PIDA-promoted direct selective C 5 -selenylations of indolines with readily available diselenides via radical process to access diversely selenylated indoline derivatives. (Scheme 1d).…”