Highly efficient oxidation of amines to imines by singlet oxygen and its application in Ugi-type reactions.
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.
Jiang
Gaoxi
G
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.
Chen
Jian
J
Huang
Jie-Sheng
JS
Che
Chi-Ming
CM
D000588:Amines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D010084:Oxidation-Reduction; D026082:Singlet Oxygen / Q000737:chemistry*
D000588:Amines; D007097:Imines; D026082:Singlet Oxygen