Title of article :
Selective copper(II)-catalyzed aerobic oxidative cleavage of aromatic gem-disubstituted alkenes to carbonyl compounds under neutral and mild conditions
Author/Authors :
Md. Munkir Hossain، نويسنده , , Shin-Guang Shyu، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2014
Pages :
5
From page :
251
To page :
255
Abstract :
Three copper(II) catalytic systems, CuCl2·2H2O, CuCl2·2H2O+phenanthroline, and [Cu(μ-Cl)Cl(phen)]2 were used to cleave alkenes to their corresponding carbonyl compounds under aerobic and neutral conditions. [Cu(μ-Cl)Cl(phen)]2 shows enhanced selectivity over the other two catalytic systems. The oxidative cleavage reactions were carried out in mixed H2O/THF solvent system under oxygen (4 atm) at 60°C. The real oxidant is 2-hydroperoxytetrahydrofuran, which is generated in situ in the process through the reaction between THF and oxygen catalyzed by copper(II). The cleavage reactions are selective for aromatic gem-disubstituted alkenes. Aromatic internal alkenes are slow to be oxidized, and both aliphatic terminal and internal alkenes are inert to oxidative cleavage. Free radical scavenger 2,2,6,6, tetramethylpiperidinyl-1-oxyl (TEMPO) deactivates the reaction indicating the involvement of free radical path in the reaction mechanism.
Keywords :
alkene , Oxidation , copper , Carbonyl , Aerobic
Journal title :
Tetrahedron
Serial Year :
2014
Journal title :
Tetrahedron
Record number :
1106639
Link To Document :
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