Diversity-oriented synthesis of fluoroalkylated amines via the palladium-catalyzed divergent fluoroalkylamination of 1,3-dienes

Chen Fu; Zhaosheng Zhang; Yuzhen Li; Dongni Gao; Zi-Ning Cui; Zhaodong Li

doi:10.1039/d2cc00983h

Diversity-oriented synthesis of fluoroalkylated amines via the palladium-catalyzed divergent fluoroalkylamination of 1,3-dienes

Chem Commun (Camb). 2022 May 5;58(37):5614-5617. doi: 10.1039/d2cc00983h.

Authors

Chen Fu¹, Zhaosheng Zhang¹, Yuzhen Li¹, Dongni Gao¹, Zi-Ning Cui^{1

2}, Zhaodong Li^{1

3}

Affiliations

¹ Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China. ziningcui@scau.edu.cn.
² State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
³ Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, China. scaulizhaodong@scau.edu.cn.

PMID: 35438113
DOI: 10.1039/d2cc00983h

Abstract

Herein, we reported the first versatile and expeditious protocol for the diversity-oriented synthesis (DOS) of fluoroalkylated amines via the photoinduced palladium-catalyzed cross coupling of 1,3-dienes, amines and fluoroalkyl iodides, which features excellent 3,4- and 1,4-selectivity controlled by fluoroalkyl iodides, a broad substrate scope as well as good function group tolerance, and could be extended to the late-stage modification of bioactive molecules.

MeSH terms

Amines* / chemistry
Catalysis
Iodides / chemistry
Palladium* / chemistry
Polyenes

Substances

Amines
Iodides
Polyenes
Palladium