Recent Advances in the Synthesis of Distal Fluorinated Ketones

doi:10.6023/A15060424

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

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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

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 E-mail:chzhu@suda.edu.cn
基金资助:
项目受国家自然科学基金(No.21402134)资助.

Recent Advances in the Synthesis of Distal Fluorinated Ketones

Fan Xuefeng, Zhao Huijun, Zhu Chen

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

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Fan Xuefeng, Zhao Huijun, Zhu Chen. Recent Advances in the Synthesis of Distal Fluorinated Ketones[J]. Acta Chim. Sinica, 2015, 73(10): 979-983.

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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

Recent Advances in the Synthesis of Distal Fluorinated Ketones

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