C70 Fullerene Catalyzed Photoinduced Aerobic Oxidation of Benzylamines to Imines and Aldehydes

被引:32
|
作者
Kumar, Inder [1 ,2 ]
Kumar, Rakesh [1 ]
Gupta, Shiv Shankar [1 ,2 ]
Sharma, Upendra [1 ,2 ]
机构
[1] CSIR Inst Himalayan Bioresource & Technol, Chem Technol Div, Palampur 176061, Himachal Prades, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 09期
关键词
METAL-FREE; CARBONYL-COMPOUNDS; MESOPOROUS CARBON; HYDROGEN-PEROXIDE; SECONDARY-AMINES; ALCOHOLS; SOLVENT; PHOTOCATALYSIS; EFFICIENT; CLEAVAGE;
D O I
10.1021/acs.joc.1c00297
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-70 fullerene catalyzed photoinduced oxidation of benzylic amines at ambient conditions has been explored here. The developed strategy's main feature includes the additive/oxidant-free conversion of benzylic amine to corresponding imine and aldehydes. The reaction manifests broad substrate scope with excellent function group leniency and is applicable up to the gram scale. Further, symmetrical secondary amines can also be synthesized from benzylic amine in a one-pot two-step process. Various experiments and density functional theory studies revealed that the current reaction involves the generation of reactive oxygen species, single electron transfer reaction, and benzyl radical formation as key steps under photocatalytic conditions.
引用
收藏
页码:6449 / 6457
页数:9
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