A Catalytic Three‐Component Aminofluorination of Unactivated Alkenes with Electron‐Rich Amino Sources

Author:

Dong Junchao1,Liang Yujie2,Li Yang13,Guan Wei2,Zhang Qian1,Fu Junkai1ORCID

Affiliation:

1. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis and Institute of Functional Material Chemistry Department of Chemistry Northeast Normal University Changchun 130024 P. R. China

2. Institute of Functional Material Chemistry Department of Chemistry Northeast Normal University Changchun 130024 P. R. China

3. Warshel Institute for Computational Biology and School of Life and Health Sciences School of Medicine The Chinese University of Hong Kong Shenzhen 518172 P. R. China

Abstract

AbstractWe present herein a copper‐catalyzed three‐component aminofluorination of unactivated alkenes with N‐bromodialkylamines and readily available nucleophilic fluoride under the assistance of a bidentate auxiliary. This protocol exhibits excellent functional group tolerance toward a wide range of unactivated alkenes and N‐bromodialkylamines to furnish the corresponding β‐fluoroalkylamines in a highly regio‐ and diastereoselective manner. The appropriate choice of nucleophilic fluoro source is essential to make this reaction a reality. Further DFT calculations show that the exothermic ion exchange between external fluoride ion and Cu(II) intermediate provides additional driving force to the irreversible migratory insertion, which offsets the unfavorable reaction energetics associated with the subsequent C(sp3)–F reductive elimination. This finding offers a new avenue to catalytic intermolecular aminofluorination of unactivated alkenes with electron‐rich amino sources via a remarkable reductive elimination of Cu(III) species to forge the C(sp3)–F bonds.

Funder

Shenzhen Science and Technology Innovation Program

Postdoctoral Research Foundation of China

Jilin Provincial Scientific and Technological Development Program

National Natural Science Foundation of China

Publisher

Wiley

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