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银催化羰基导向炔烃的区域选择性氟化:α-氟代酮的合成。

Silver-Catalyzed Regioselective Fluorination of Carbonyl Directed Alkynes: Synthesis of α-Fluoroketones.

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University , Suzhou 215123, China.

出版信息

Org Lett. 2017 Apr 7;19(7):1662-1665. doi: 10.1021/acs.orglett.7b00453. Epub 2017 Mar 15.

Abstract

A novel silver-catalyzed fluorination reaction of carbonyl directed alkynes in the presence of N-fluorobenzenesulfonimide and water with high regioselectivities has been developed. The established protocol provides an alternative method for rapid assembly of α-fluoroketone derivatives under simple and mild reaction conditions. The reaction pathway involves a ring closure and opening process for the construction of new C-O and C-F bonds. In addition, a fluorine-containing indanone was observed through further N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reaction of α-fluoroketone.

摘要

一种新型的银催化羰基导向炔烃的氟化反应,在 N-氟代苯磺酰胺和水的存在下,具有高区域选择性。该方法提供了一种在简单温和的反应条件下快速合成α-氟代酮衍生物的替代方法。该反应途径涉及环闭合和开环过程,用于构建新的 C-O 和 C-F 键。此外,还通过α-氟代酮的 N-杂环卡宾催化的分子内交叉安息香反应进一步观察到含氟茚酮。

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