Cp*Co(iii)-catalyzed N-alkylation of amines with secondary alcohols

被引:52
作者
Emayavaramban, Balakumar [1 ]
Chakraborty, Priyanka [1 ]
Manoury, Eric [2 ]
Poli, Rinaldo [2 ]
Sundararaju, Basker [1 ]
机构
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[2] Univ Toulouse, UPS, INPT, Fine CNRS,LCC, 205 Route Narbonne, F-31077 Toulouse 4, France
关键词
H BOND FUNCTIONALIZATION; IRIDIUM-CATALYZED ALKYLATION; ASTERISK-IR COMPLEX; ONE-POT SYNTHESIS; C-H; REDUCTIVE AMINATION; EFFICIENT CATALYSTS; AROMATIC-AMINES; COOPERATIVE CATALYSIS; ASYMMETRIC-SYNTHESIS;
D O I
10.1039/c8qo01389f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hydrogen borrowing methodology is a well-known, environmentally benign method for the direct alkylation of amines and alcohols as it produces only water as a side product. However, the direct alkylation of amines with secondary alcohols using first-row transition metals is very challenging. We herein report for the first time Cp*Co(iii)-catalyzed direct N-alkylation of amines starting from secondary alcohols. The reaction tolerates a wide variety of functional groups, including various aryl amines and amides. Our preliminary mechanistic investigations and DFT calculations suggest that [Cp*CoI2] is an active species, that PCy3 stabilizes the high-valent hydride intermediate, and that the reaction indeed proceeds through hydrogen auto-transfer processes.
引用
收藏
页码:852 / 857
页数:6
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