Selective Radical Fluorination of Tertiary Alkyl Halides at Room Temperature

He Chen; Zhonglin Liu; Ying Lv; Xinqiang Tan; Haigen Shen; Hai-Zhu Yu; Chaozhong Li

doi:10.1002/anie.201708197

Selective Radical Fluorination of Tertiary Alkyl Halides at Room Temperature

Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15411-15415. doi: 10.1002/anie.201708197. Epub 2017 Nov 2.

Authors

He Chen¹, Zhonglin Liu¹, Ying Lv², Xinqiang Tan¹, Haigen Shen¹, Hai-Zhu Yu², Chaozhong Li^{1

3}

Affiliations

¹ Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
² AnHui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Anhui University, Hefei, Anhui, 230601, P. R. China.
³ School of Materials and Chemical Engineering, Ningbo University of Technology, 201 Fenghua Road, Ningbo, 315211, P. R. China.

PMID: 29024259
DOI: 10.1002/anie.201708197

Abstract

Direct fluorination of tertiary alkyl bromides and iodides with Selectfluor is described. The halogen-exchange fluorination proceeds efficiently in acetonitrile at room temperature under metal-free conditions and exhibits a wide range of functional group compatibility. Furthermore, the reactions are highly selective in that alkyl chlorides and primary and secondary alkyl bromides remain intact. A radical mechanism is proposed for this selective fluorination.

Keywords: alkyl halides; fluorination; halogen exchange; radicals; synthetic methods.

Publication types

Research Support, Non-U.S. Gov't