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


雍学锋a,b,c,d, 黄建强b,c,d, 何振宇b,c,d   

  1. 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;
  • 基金资助:

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

Yong Xue-Fenga,b,c,d, Huang Jian-Qiangb,c,d, Ho Chun-Yub,c,d   

  1. 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).

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