title: Highly efficient oxidation of amines to imines by singlet oxygen and its application in Ugi-type reactions.
abstract: A variety of secondary benzylic amines were oxidized to imines in 90% to >99% yields by singlet oxygen generated from oxygen and a porphyrin photosensitizer. On the basis of these reactions, a protocol was developed for oxidative Ugi-type reactions with singlet oxygen as the oxidant. This protocol has been used to synthesize C1- and N-functionalized benzylic amines in up to 96% yields.
authors.affiliation: Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China.
authors.forename: Gaoxi
authors.initials: G
authors.lastname: Jiang
authors.forename: Jian
authors.initials: J
authors.lastname: Chen
authors.forename: Jie-Sheng
authors.initials: JS
authors.lastname: Huang
authors.forename: Chi-Ming
authors.initials: CM
authors.lastname: Che
mesh_terms: D000588:Amines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D010084:Oxidation-Reduction; D026082:Singlet Oxygen / Q000737:chemistry*
chemical_list: D000588:Amines; D007097:Imines; D026082:Singlet Oxygen