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Efficient Vanadium‐Catalyzed Aerobic C−C Bond Oxidative Cleavage of Vicinal Diols
Author(s) -
Amadio Emanuele,
GonzálezFabra Joan,
Carraro Davide,
Denis William,
Gjoka Blerina,
Zonta Cristiano,
Bartik Kristin,
Cavani Fabrizio,
Solmi Stefania,
Bo Carles,
Licini Giulia
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800050
Subject(s) - chemistry , vicinal , vanadium , catalysis , chemoselectivity , bond cleavage , cleavage (geology) , oxygen , oxidative cleavage , medicinal chemistry , dehydrogenation , photochemistry , density functional theory , organic chemistry , computational chemistry , geotechnical engineering , fracture (geology) , engineering
The aerobic oxidative C−C bond cleavage of vicinal diols catalyzed by vanadium amino triphenolates is described. Our results show that C−C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or aliphatic substituents) affording the corresponding carbonyl derivatives with high chemoselectivity. Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to 4150 h −1 . A reaction mechanism, rationalized by density functional theory calculations, is also proposed.