铜催化未活化C(sp³)-H键的分子内酰胺化反应合成N-取代吲哚啉
Cu-Catalyzed Intramolecular Amidation of Unactivated C(sp(3) )-H Bonds To Synthesize N-Substituted Indolines.
作者信息
Pan Fei, Wu Bin, Shi Zhang-Jie
机构信息
Beijing National Laboratory of Molecular Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, P. R. China.
State Key Laboratory of Organometallic Chemistry, CAS, Shanghai, 200032, P. R. China.
出版信息
Chemistry. 2016 May 4;22(19):6487-90. doi: 10.1002/chem.201600680. Epub 2016 Mar 24.
A copper-catalyzed intramolecular amidation of unactivated C(sp(3) )-H bonds to construct indoline derivatives has been developed. Such an amidation proceeded well at primary C-H bonds preferred to secondary C-H bonds. The transformation owned a broad substrate scope. The corresponding indolines were obtained in good to excellent yields. N-Formal and other carbonyl groups were suitable and were easily deprotected and transformed into methyl or long-chained alkyl groups. Preliminary mechanistic studies suggested a radical pathway.
已开发出一种铜催化的未活化C(sp(3) )-H键的分子内酰胺化反应，用于构建二氢吲哚衍生物。这种酰胺化反应在伯C-H键上比仲C-H键上进行得更好。该转化反应具有广泛的底物范围。相应的二氢吲哚以良好至优异的产率得到。N-甲酰基和其他羰基是合适的，并且易于脱保护并转化为甲基或长链烷基。初步机理研究表明是自由基途径。
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