Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (10): 979-983.DOI: 10.6023/A15060424 Previous Articles     Next Articles


羰基兼容的氟代反应及远端氟代脂肪酮合成的近期进展 2016 Awarded

范雪峰, 赵会君, 朱晨   

  1. 苏州大学材料与化学化工学部 江苏省有机合成重点实验室 苏州 215123
  • 投稿日期:2015-06-19 发布日期:2015-09-15
  • 通讯作者: 朱晨
  • 基金资助:


Recent Advances in the Synthesis of Distal Fluorinated Ketones

Fan Xuefeng, Zhao Huijun, Zhu Chen   

  1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2015-06-19 Published:2015-09-15
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21402134).

Incorporation of a fluorine atom to molecules is a privileged strategy to modify the physical, chemical and biological properties, which is widely executed in pharmaceuticals, agrochemical and material sciences. Consequently, the development of efficient and direct fluorination approach is of considerable significance. In spite of the great progress made in the transition-metal catalyzed construction of sp2 C—F bond via C—H activation and cross-coupling reactions, the direct access to aliphatic sp3 C—F bond is relatively underdeveloped as the development of a mild and efficient method to construct sp3 C—F bond remains a challenging issue. Ketone is a ubiquitous and important structural motif in organic compounds. The efficient synthesis of fluorinated ketone building blocks thus provides a shortcut for the introduction of fluorinated functionalities into complex molecules. Other than α-fluorinated ketones, the synthesis of distal fluorinated ketones is still challenging. Herein, we highlight the recent efforts made for the synthesis of distal fluorinated ketones. Four fluorination pathways are described: (a) C—H fluorination, (b) decarboxylative fluorination and deboronofluorination; (c) olefin fluorination, and (d) ring-opening fluorination. The first and second sections briefly introduce the direct sp3 C—H fluorination, decarboxylative fluorination, and deboronofluorination to construct aliphatic sp3 C—F bonds, which are tolerant to carbonyl group in the substrates. The third section discusses the direct construction of β and γ-fluorinated ketones via the difunctionalization of olefins. The last section puts an emphasis on the latest emergence of ring-opening fluorination. Relying on the “radical clock” strategy, the distal fluorinated ketones can be obtained from the corresponding tertiary cycloalkanols. Overall, this highlight provides a new insight into the recent advances in the sp3 C—H fluorination and the synthesis of distal fluorinated ketones.

Key words: fluorination, C—H activation, decarboxylation, olefin difunctionalization, ring opening