Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 215-222.DOI: 10.6023/cjoc201808014 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞 元素有机化学合辑2018-2019 镍催化有机反应合辑

Articles

镍催化下一溴二氟甲烷对(杂)芳基溴代物的二氟甲基化反应

高兴, 何旭, 张新刚   

  1. 中国科学院上海有机化学研究所 分子合成卓越中心 中国科学院有机氟化学重点实验室 上海 200032
  • 收稿日期:2018-08-15 修回日期:2018-09-14 出版日期:2019-01-25 发布日期:2018-10-12
  • 通讯作者: 张新刚 E-mail:xgzhang@sioc.ac.cn
  • 基金资助:

    国家重点基础研究发展计划(973计划,No.2015CB931900)、国家自然科学基金(Nos.21425208,21672238,21332010,21421002)和中国科学院先导专项(No.XDB20000000)资助项目.

Nickel-Catalyzed Difluoromethylation of (Hetero)aryl Bromides with BrCF2H

Gao Xing, He Xu, Zhang Xingang   

  1. Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-08-15 Revised:2018-09-14 Online:2019-01-25 Published:2018-10-12
  • Contact: 10.6023/cjoc201808014 E-mail:xgzhang@sioc.ac.cn
  • Supported by:

    Project supported by the National Basic Research Program of China (973 Program, No. 2015CB931900), the National Natural Science Foundation of China (Nos. 21425208, 21672238, 21332010, 21421002), and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000).

A nickel-catalyzed direct difluoromethylation of (hetero)aryl bromides with bromodifluoromethane (BrCF2H) is described. This reaction features high efficiency, broad substrate scope and high functional group tolerance, providing a cost-efficient and straightforward route for applications in medicinal chemistry. Preliminary mechanistic studies reveal that a nickel-based, reductive cross-coupling catalytic cycle is involved in the reaction.

Key words: aryl bromide, bromodifluoromethane, difluoromethylation, nickel, reductive cross-coupling