Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2726-2734.DOI: 10.6023/cjoc201903063 Previous Articles     Next Articles

Special Issue: 元素有机化学合辑2018-2019 有机氟化学合辑



陶雪芬a*(), 盛荣b, 鲍堃b, 王玉新a, 金银秀a   

  1. a 台州职业技术学院 台州 318000
    b 浙江大学药学院 浙江省抗癌药物研究重点实验室 杭州 310058
  • 收稿日期:2019-03-27 修回日期:2019-04-30 发布日期:2019-06-12
  • 通讯作者: 陶雪芬
  • 基金资助:

Progress of Difluoromethyl Heteroaryl Sulfones as Difluoroalkylation Reagents

Tao Xuefena*(), Sheng Rongb, Bao Kunb, Wang Yuxina, Jin Yinxiua   

  1. a Taizhou Vocational & Technical College, Taizhou 318000;
    b Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences,Zhejiang University, Hangzhou 310058
  • Received:2019-03-27 Revised:2019-04-30 Published:2019-06-12
  • Contact: Tao Xuefen
  • Supported by:
    Project supported by the Zhejiang Education Department(FG2018166)

Due to the uniqueness of fluorine atom and C—F bond, difluoromethylene has special properties. As a bioisostere of an oxygen or a carbonyl group, it plays an important role in medicines, pesticides and materials. Difluoromethyl heteroaryl sulfones, represented by 2-PySO2CF2H (Hu reagent), have been developed recently as difluoromethylation reagents, and widely recognized by synthetic chemists for their ease of preparation, good functional group tolerance and universal applicability to a wide range of carbonyl compounds. Through different types of reactions such as nucleophilic substitution, nucleophilic addition, Julia-Kocienski olefination reaction, and radical-mediated difunctionalization, they introduced difluoromethyl, difluoromethylene, gem-difluoroalkene and other fluorine-containing groups into aldehydes, ketones, and heterocyclic compounds. For the first time, the synthesis of fluorine-containing organic compounds involved in various difluoromethyl heteroaryl sulfones in the past decade is reviewed from the perspective of reaction types and their application studies.

Key words: difluoromethyl heteroaryl sulfones, nucleophilic reaction, Julia-Kocienski olefination, radical-mediated difunctionalization