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Copper(I) Catalyzed Differential Peroxidation of Terminal and Internal Alkenes Using TBHP
Author(s) -
Mir Bilal Ahmad,
Rajamanickam Suresh,
Begum Pakiza,
Patel Bhisma K.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901689
Subject(s) - chemistry , alkene , acetonitrile , carbonylation , tert butyl hydroperoxide , catalysis , indene , aryl , organic chemistry , medicinal chemistry , solvent , alkyl , carbon monoxide
Terminal and internal alkenes react contrarily with tert ‐butyl hydroperoxide (TBHP) giving various products. A Cu(I) catalyzed decarbonylative C–C bond formation followed by a carbonylation–peroxidation of vinyl arenes has been achieved using tert ‐butyl hydroperoxide (TBHP) as the oxidant in acetonitrile. Whereas, α‐methyl styrenes yielded aryl methyl ketones and the α‐substituted unsymmetrical internal alkenes afforded selective α‐peroxidation under the identical reaction conditions. Concurrent peroxidation–carbonylation–cycloalkylation/cycloetherifiction of internal cyclic alkene such as indene is achieved by switching the solvent system from acetonitrile to cycloalkanes/cyclic ether. All these reactions proceed via radical paths generating interesting peroxo‐compounds.