Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines

被引:27
作者
Ghosh, Santanu [1 ]
Jana, Chandan K. [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
关键词
AMIDE BOND FORMATION; CATALYZED CONVERSION; GOLD NANOPARTICLES; CYCLIC AMINES; OXIDATION; ALDEHYDES; AMIDATION; ARYLATION; NITRILES; ALCOHOLS;
D O I
10.1021/acs.joc.7b02630
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct oxidation of alpha-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
引用
收藏
页码:260 / 266
页数:7
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