Rh-catalyzed tunable defluorinative borylation

Fei Hao; Xueyun Shang; Zhenwei Liu; He Zhang; Jin-Hong Lin; Ji-Chang Xiao

doi:10.1039/d1cc02079j

Rh-catalyzed tunable defluorinative borylation

Chem Commun (Camb). 2021 Jul 20;57(58):7124-7127. doi: 10.1039/d1cc02079j.

Authors

Fei Hao¹, Xueyun Shang², Zhenwei Liu², He Zhang³, Jin-Hong Lin⁴, Ji-Chang Xiao³

Affiliations

¹ Shandong Provincial Key Laboratory of Molecular Engineering, Qilu University of Technology-Shandong Academy of Science, Ji'nan 250353, China and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. zhanghe07@gmail.com jlin@sioc.ac.cn jchxiao@sioc.ac.cn.
² Shandong Provincial Key Laboratory of Molecular Engineering, Qilu University of Technology-Shandong Academy of Science, Ji'nan 250353, China.
³ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. zhanghe07@gmail.com jlin@sioc.ac.cn jchxiao@sioc.ac.cn.
⁴ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. zhanghe07@gmail.com jlin@sioc.ac.cn jchxiao@sioc.ac.cn and Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. China. jlin@shu.edu.cn.

PMID: 34179910
DOI: 10.1039/d1cc02079j

Abstract

Described herein is a Rh-catalyzed tunable defluorinative borylation of allylic gem-difluorides to provide allylborylated monofluoroalkenes or homoallylborylated monofluoroalkenes with excellent Z/E selectivities. Completely different reaction paths were observed by slightly changing the reaction conditions. Allylborylated monofluoroalkenes were further converted into dihydroxyl-containing monofluoroalkenes.