Applications of (NHC)Ni(II) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades

doi:10.6023/cjoc202005050

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3327-3337.DOI: 10.6023/cjoc202005050 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

(NHC)Ni(II)催化的[3+2]氢烯化重排串联反应的应用

雍学锋^a,b,c,d, 黄建强^b,c,d, 何振宇^b,c,d

a 哈尔滨工业大学化学与化工学院哈尔滨 150001;
b 深圳格拉布斯研究院广东深圳 518055;
c 广东省催化化学重点实验室广东深圳 518055;
d 南方科技大学化学系广东深圳 518055

收稿日期:2020-05-19 修回日期:2020-07-02 发布日期:2020-07-17
通讯作者: 黄建强, 何振宇 E-mail:huangjq3@sustech.edu.cn;jasonhcy@sustech.edu.cn
基金资助:
广东省基础与应用基础研究基金-青年基金（No.2019A1515110001）资助项目.

Applications of (NHC)Ni(II) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades

Yong Xue-Feng^a,b,c,d, Huang Jian-Qiang^b,c,d, Ho Chun-Yu^b,c,d

a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001;
b Shenzhen Grubbs Institute, Shenzhen, Guangdong 518055;
c Guangdong Provincial Key Laboratory of Catalysis, Shenzhen, Guangdong 518055;
d Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Received:2020-05-19 Revised:2020-07-02 Published:2020-07-17
Supported by:
Project supported by the Guangdong Basic and Applied Basic Research Foundation-Youth Project (No. 2019A1515110001).

1. cjoc202005050.pdf(2343KB)

Abstract

Synthetic applications of the recently developed (NHC)Ni(Ⅱ) catalyzed[3+2] hydroalkenylation-rearrangement cascade (HARC) were investigated. The foundations of these highly substituted cyclopentadienes and methylene cyclopentanes formation were compared with typical cross-hydroalkenylation of alkenes and dienes. The desired cyclization products were examined as key starting materials for a range of olefin functionalization methodology, including Diels-Alder, epoxidation, ozonolysis, halogenation-rearrangement and fluorohydroxylation. The results showed that several very interesting carbon skeletons can be obtained easily with high diastereoselectivity in one step or in cascade.

Key words: strained alkene, [3+2] cycloaddition, N-heterocycle carbenes, Ni catalysis, cross-hydroalkenylation

Cite this article

Yong Xue-Feng, Huang Jian-Qiang, Ho Chun-Yu. Applications of (NHC)Ni(II) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3327-3337.

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(NHC)Ni(II)催化的[3+2]氢烯化重排串联反应的应用

Applications of (NHC)Ni(II) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades

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