Mechanochemically Induced Chalcogenation of Bicyclic Arenes under Solvent‐, Ligand‐, Metal‐, and Oxidant‐Free Conditions

Abstract

A convenient method has been developed for the synthesis of biarenyl chalcogenides through the interaction of bicyclic arenes and diaryl dichalcogenides on the surface of basic alumina under ball milling without any metal catalyst or solvent. This methodology shows wide substrate scope and is of high potential in organic synthesis due to its green aspects of ease of operation, shorter reaction time, ambient conditions and high yields.

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“…Very recently, in 2020, Ranu and co-workers reported a mechanochemically mediated protocol for the selenylation of 2-naphthols 9 , employing diaryl diselenides 6 as the selenylating agent in the absence of TM-catalyst, oxidants and solvent [ 99 ]. The protocol was conducted in a five-ball reactor, operating at 600 rpm for 1 h, in the presence of basic Al 2 O 3 (washed with a 15% KOH solution and dried).…”

“…Under the optimized reaction condition, twenty 1-selenyl-2-naphthols 11 were prepared in good to excellent yields, presenting an excellent tolerance to several electron-rich and electron-deficient 2-naphthols and diaryl diselenides (Scheme 40). Very recently, in 2020, Ranu and co-workers reported a mechanochemically mediated protocol for the selenylation of 2-naphthols 9, employing diaryl diselenides 6 as the selenylating agent in the absence of TM-catalyst, oxidants and solvent [99]. The protocol was conducted in a five-ball reactor, operating at 600 rpm for 1 h, in the presence of basic Al 2 O 3 (washed with a 15% KOH solution and dried).…”

Solvent free synthesis of organoselenides under green conditions

“…Recently, Ranu and coworkers introduced a convenient metal and oxidant free protocol for the synthesis of biarenyl selenides ( 27 ) by the reaction of β-naphthols and diaryl diselenides on the surface of basic alumina under ball milling at ambient temperature (5 balls, 600 rpm) (Scheme 22). 28 This is the first example of mechanochemically induced regioselective C–H selenylation of arenes at the α-position of 2-naphthols or bicyclic (hetero) arenes in the absence of additives, ligands and solvents under an air atmosphere. Interestingly, after completion, the reaction mixture was directly subjected to column chromatography for purification without involving any conventional work-up process which minimizes the use of hazardous volatile solvents.…”

Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides

“…Many molecules containing a thioether structure have been proved to have important application values in the fields of medicine, materials, dyes, and so on . Because of the synthetic versatility of sulfur compounds in organic synthesis, chemists are continually looking for efficient preparation strategies for multifunctional sulfide compounds.…”