Tin-Catalyzed Selective Reductive Hydroamination of Alkynes for the Synthesis of Tertiary Amines

被引：12
|
作者：
Nayal, Onkar S. [1 ,2 ]
Thakur, Maheshwar S. [1 ,2 ]
Kumar, Manoranjan [1 ,2 ]
Sharma, Sushila [1 ,2 ]
Kumar, Neeraj [1 ,2 ]
机构：
[1] CSIR, Inst Himalayan Bioresource Technol, Dept Nat Prod Chem & Proc Dev, Palampur 176061, Himachal Prades, India
[2] Acad Sci & Innovat Res, 2 Rafi Marg, New Delhi 110001, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 07期
关键词：
alkynes; C-N cross coupling; hydroamination; secondary amines; tertiary amines; SECONDARY-AMINES; CARBONYL-COMPOUNDS; INTERNAL ALKYNES; TERMINAL ALKYNES; NATURAL-PRODUCTS; AMINATION; ALKENES;
D O I：
10.1002/adsc.201501088
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A unique preference of tin(II) for aniline activation is disclosed. In the present work tin(II) triflate-catalyzed highly selective Markovnikov reductive hydroamination of internal as well as terminal alkynes is reported. The mechanistic study revealed the involvement of two steps in one pot wherein alkyne reduces to corresponding alkene in presence of PMHS as reducing agent followed by hydroamination of alkene. A broad range of alkynes transformed into tertiary amines with good to excellent yield. This method is equally applicable in synthesis of secondary amines.
引用
收藏
页码：1103 / 1109
页数：7
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