Carbonyl-Assisted Iridium-Catalyzed C–H Amination Using 2,2,2-Trichloroethoxycarbonyl Azide

The carbonyl-directed, mono C–H amination of arenes has been achieved using [Cp*Ir­(III)­Cl2]2 as the catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating reagent. The amination proceeds smoothly with a variety of arylcarbonyl compounds, including alkyl and vinyl arylketones, seco...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (21), p.13990-14004
Main Authors: Dong, Xunqing, Shang, Mingzhou, Chen, Shuguang, Zhang, Tao, Jalani, Hitesh B., Lu, Hongjian
Format: Article
Language:English
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Summary:The carbonyl-directed, mono C–H amination of arenes has been achieved using [Cp*Ir­(III)­Cl2]2 as the catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating reagent. The amination proceeds smoothly with a variety of arylcarbonyl compounds, including alkyl and vinyl arylketones, secondary and tertiary aryl amides, and acetyl indoles. The resulting ortho-TrocNH arylcarbonyl compounds are easily transformed to the corresponding free arylamines, aryl carbamates, or aryl ureas. Taking advantage of the electrophilic nature of both Troc and carbonyl groups in ortho-TrocNH arylcarbonyl compounds, the subsequent cyclization with dinucleophilic reagents has also been demonstrated. This provides an efficient strategy for the construction of aryl-fused N-heterocycles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01636