Synthesis of Skipped Aminodienes by a Ni-Catalyzed Ring-Opening/Cross-Coupling Reaction of Vinylaziridines with Multifunctional Organoboronic Acids

被引：6

作者：

Zhang, Lu ^{[1
,2
]}

Du, Qingfeng ^{[2
]}

Luo, Yicong ^{[2
]}

Wang, Yuanlin ^{[2
]}

Gao, Feng ^{[2
]}

Ye, Yong ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, 100 Kexue Rd, Zhengzhou 450001, Henan, Peoples R China

[2] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 22期

基金：

中国国家自然科学基金;

关键词：

DFT calculation; Multifunctional organoboronic acids; Ni-catalyzed; Ring-opening; Skipped aminodiene; VINYL AZIRIDINES; ENANTIOSELECTIVE SYNTHESIS; BOND FORMATION; 1,3-DIENES; EFFICIENT; EPOXIDES; OLEFINS; 1,4-DIFUNCTIONALIZATION; CONSTRUCTION; HETEROCYCLES;

D O I：

10.1002/cjoc.202300313

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Skipped dienes are of great importance but remain challenging to synthesize because of the presence of a sp(3) hybrid carbon between the two alkenes. Herein, we have developed the first nickel-catalyzed regio-, (E)-stereo- and linear-selective ring-opening/cross-coupling reaction of vinylaziridines with organoboronic acids under mild conditions to construct various skipped aminodienes. The reaction exhibits wide functional-group compatibility, and could be adapted for the introduction of skipped aminodiene functionality into bioactive molecules. In addition, the reaction could be carried out on a gram-scale, delivering the ring-opening products in high yields and with linear-selectivity (90% yield, l : b >20 : 1). Furthermore, DFT calculations and mechanistic experiments provided detailed insights into the mechanism.

引用

页码：3003 / 3011

页数：9

共 98 条

[21] Catalytic Arylalkylation of Alkenyl Amines at Remote Sites via Directed Nickel Catalysis [J].