Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process

被引：23
|
作者：
Li, Ze-Lin [1 ]
Sun, Kang-Kang [1 ]
Wu, Peng-Yu [1 ]
Cai, Chun [1 ,2 ]
机构：
[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Lu, Shanghai 20032, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 11期
基金：
中国国家自然科学基金;
关键词：
PRIMARY AMINES; INTERMOLECULAR HYDROAMINOALKYLATION; REDUCTIVE AMINATION; SELECTIVE SYNTHESIS; ONE-POT; EFFICIENT; NITRILES; ALKENES; N-(CYCLOHEXYLMETHYL)-N-ALKYLAMINES; TETRACARBONYLHYDRIDOFERRATE;
D O I：
10.1021/acs.joc.9b00625
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The iron-catalyzed alpha-C-H alkylation of N-methylanilines without any directing group by cross-dehydrogenative coupling between unactivated C(sp(3))-H and C(sp(3))-H bonds has been established for the first time, which provides a good complement to C(sp(3))-H activation reactions and expands the field of Fe-catalyzed C-H functionalizations. Many different C(sp(3))-H bonds in cyclic alkanes, cyclic ethers, and toluene derivatives can be used as coupling partners. Mechanistic investigations including the radical reaction process, the main role of various reagents, and the kinetic isotope effect experiment were also described.
引用
收藏
页码：6830 / 6839
页数：10
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