Benzylic intermolecular carbon-carbon bond formation by selective anodic oxidation of dithioacetals.
[reaction: see text]. Novel anodic intermolecular carbon-carbon bond formation has been accomplished by the oxidative carbon-sulfur bond fission of benzylic dithioacetals to give a wide variety of aromatic compounds. The substitution reaction successfully took place by the selective anodic oxidation of a sulfur atom of a dithioacetal. Stepwise double-substitution reactions were also achieved by the regulation of oxidation potential.
Chiba
K
K
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan. chiba@cc.tuat.ac.jp
Uchiyama
R
R
Kim
S
S
Kitano
Y
Y
Tada
M
M
D000080:Acetals / Q000378:metabolism*; D000475:Alkenes / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry*
D000080:Acetals; D000475:Alkenes; D002244:Carbon; D001554:Benzene; D010100:Oxygen