Arylselenyl Radical-Mediated Cyclization of N-(2-Alkynyl)anilines: Access to 3-Selenylquinolines

Abstract

An efficient and novel approach to accessing 3-selenylquinolines from diaryl diselenides and acyclic, selenium-free substrates is described. Preliminary mechanistic studies indicate that the combination of CuCl2 and air affords an appropriate environment for producing arylselenyl radicals that initiate the cascade cyclization of N-(2-alkynyl)­anilines, forming key Se–C and C–C bonds in a single step. Using this chemistry, a wide variety of 3-selenylquinolines were produced in moderate to excellent yield under mild conditions, highlighting the versatility and usefulness of this new method.

N-Fluorobenzenesulfonimide-Mediated Intermolecular Carboselenenylation of Olefins with Aromatics and Diselenides

“…13 C{ 1 H} NMR (100 MHz, CDCl 3 ): 143.1, 141.6, 140.4, 132.5, 131.6, 129.4, 129.3, 128.6, 128.3, 128.0, 127.5, 127.3, 127.2, 122.6. The data are in accordance with the literature …”

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

“…In this reaction, CuCl 2 was used to generate organoselenyl radical, which promoted the cyclization of the corresponding amines (Scheme 51). [82] Alkynamides can be efficiently cyclized to quinolinone derivatives using diorganyl diselenides under ionic or radical conditions. In 2014, we described an ionic pathway for the synthesis of 3-organoselenyl quinolinones 51 by the reaction of N-arylpropiolamides and diorganyl diselenides in the presence of iron(III) chloride (Scheme 52).…”

“…In this reaction, CuCl 2 was used to generate organoselenyl radical, which promoted the cyclization of the corresponding amines (Scheme 51). [82] …”

Electricity-driven, oxidative C–H selenylative and tellurylative annulation of N-(2-alkynyl)anilines: sustainable synthesis of 3-selanyl/tellanylquinolines

“…amounts and hazardous chlorinated solvent, DCM (Scheme 1C). 10 Despite notable advancement, the developed methods suffered from several serious limitations, such as (a) the requirement of hazardous PhSeBr or metallic reagents in over stoichiometric amounts, (b) limited substrate scope, (c) poor yield of products, (d) poor atom economy, (e) generation of Se- and/or Fe- and Cu-based stoichiometric waste. Moreover, these protocols were hardly employed for the tellurylative annulations and were only limited to synthesizing 3-selanylquinolines.…”