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Dichalcogenides/Oxone ® ‐Mediated Cyclization of ( Z )‐Chalcogenoenynes under Ultrasound Irradiation
Author(s) -
Soares Liane K.,
Barcellos Angelita M.,
Neto José S. S.,
Alves Diego,
Lenardão Eder J.,
Rosati Ornelio,
Santi Claudio,
Perin Gelson
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002252
Subject(s) - chemistry , electrophile , yield (engineering) , diselenide , solvent , medicinal chemistry , oxidative cleavage , bond cleavage , ethanol , diphenyl diselenide , nuclear chemistry , organic chemistry , selenium , catalysis , materials science , metallurgy
3‐Selanyl‐ and 3‐tellanylchalcogenophenes were prepared by the electrophilic cyclization of ( Z )‐chalcogenoenynes under ultrasound irradiation conditions. This green procedure was carried out using Oxone ® as an inexpensive and non‐toxic oxidant agent to promote the oxidative cleavage of Se−Se and Te−Te bonds. The electrophilic cyclization of ( Z )‐1‐propylthio‐ and ( Z )‐1‐butylselen‐1‐en‐3‐ynes was performed using the diaryl diselenide or ditelluride/Oxone ® /ethanol system. The respective 3‐arylselanyl and 3‐aryltellanylthiophenes and selenophenes were obtained in 40 % to 87 % yield (16 examples). Similarly, 3‐arylselanyl and 3‐aryltellanyltellurophenes were synthesized by the cyclization of ( Z )‐1‐butyltelluro‐1‐en‐3‐ynes, using glycerol as the solvent instead ethanol (5 examples; 28 % to 65 % yield). For the first time, Oxone ® was used in the selective oxidative cleavage of the Te−Te bond in cyclization reactions.