Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes

被引：15

作者：

Sun, Feilong ^{[1
]}

Yang, Chengxi ^{[2
]}

Ni, Jie ^{[2
]}

Cheng, Gui-Juan ^{[2
]}

Fang, Xianjie ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

[2] Chinese Univ Hong Kong Shenzhen, Sch Life & Hlth Sci, Warshel Inst Computat Biol, Shenzhen Key Lab Steroid Drug Discovery & Dev, Shenzhen 518172, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 10期

基金：

中国国家自然科学基金;

关键词：

ENYNES; 1,3-ENYNES;

D O I：

10.1021/acs.orglett.1c01262

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported. When appropriate bisphosphine and phosphine-phosphite ligands are applied, the same starting materials can be converted into two different enynyl nitriles with good yields and high regioselectivities. The DFT calculations unveiled that the structural features of different ligands bring divergent alkyne insertion modes, which in turn lead to different regioselectivities. Moreover, the synthetic value of the cyano-containing 1,3-enynes has been demonstrated with several downstream transformations.

引用

页码：4045 / 4050

页数：6