Nickel-catalyzed regioselective hydrocyanation of terminal alkynes by assistance of a tosyl group

被引：12
|
作者：
Arai, Shigeru [1 ,2 ]
Nakazawa, Koichi [1 ]
Yang, Xiao-fei [1 ]
Nishida, Atsushi [1 ,2 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
[2] Chiba Univ, Mol Chiral Res Ctr, 1-33 Yayoi Cho, Chiba 2638522, Japan
来源：
TETRAHEDRON | 2019年 / 75卷 / 17期
基金：
日本学术振兴会;
关键词：
Alkynes; Hydrocyanation; Iron; Nickel; Sulfonamide; STEREOSELECTIVE HYDROCYANATION; HYDROGEN-CYANIDE; OLEFINS; CYCLIZATION; STEREOCHEMISTRY; LIGANDS; ALLENES; ROUTE;
D O I：
10.1016/j.tet.2019.03.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nickel-catalyzed regioselective hydrocyanation of terminal alkynes is described. A tosylamide functionality at the propargyl position was the most suitable group for controlling the regiochemistry for C-CN bond formation as well as rate enhancement. A gram-scale synthesis was achieved by minimizing the catalyst loading to 2 mol%. The major HCN adduct could be transformed to the corresponding indoline through construction of a benzylic quaternary carbon under iron catalysis. (C) 2019 Published by Elsevier Ltd.
引用
收藏
页码：2482 / 2485
页数：4
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