An Efficient One-Pot Synthesis of Symmetrical Diselenides or Ditellurides from Halides with CuO Nanopowder/Se⁰ or Te⁰/Base

Abstract

A CuO nanopowder-catalyzed coupling reaction of aryl, alkyl, and heteroaryl iodides with elemental selenium and tellurium takes place in the presence of KOH at 90 degrees C in DMSO. A wide range of substituted symmetrical diselenides and ditellurides were afforded with good to excellent yields.

Copper‐Mediated One‐Pot Transformation of 2‐N‐Sulfonyl‐ aminoaryl Diselenides into Benzo[b][1,4]selenazines

“…[10] However, reacting 4 with 1 equivalent of Et 3 N and 2 equivalents of styrene 6a, as suitable trapping electron-rich dienophile, in CHCl 3 at 60 8C, i.e., under the reaction conditions that we found to be effective for the generation of o-imonothioquinones, [5] no reaction occurred and the starting diselenide 4 was recovered almost quantitatively after an acid work-up. Thus, although the pK a values indicated that the selenolate ion should be a better leaving group than the phthalimide anion, the Se À Se bond in 4 was not broken under the reaction conditions tested.…”

Asymmetric Methoxyselenenylations with Chiral Selenium Electrophiles

“…The starting material for the one-step synthesis is bis(2-hydroxyphenyl) diselenide (6), which is easily prepared from 2-bromophenol (5). [9] A subsequent Mitsunobu reaction can be successfully used with different chiral alcohols 7 under very mild conditions to generate the required diselenides 8 in high yields (Scheme 2). This reaction proceeds with clean inversion of the stereocenter, as no diastereomeric diselenide was detected by NMR spectroscopy.…”

Microwave-assisted one-pot synthesis of symmetrical dichalcogenides catalyzed by CuO nanopowder

“…2 Recently we developed a new methodology to synthesis a wide range of organodiselenides and ditelurides, through cross-coupling reaction of selenium or tellurium and aryl halides using CuO nanopowder as catalyst. 3 So we describe here an improved microwaveassisted method to prepare organodiselenides, ditelurides and disulfides using CuO nanoparticles as catalyst.…”