Bifunctional 1,8-Diazabicyclo[5.4.0]undec-7-ene for Visible Light-Induced Heck-Type Perfluoroalkylation of Alkenes

Lin Tang*, Ge Lv, Ya Fu, Xue-Ping Chang*, Ruimin Cheng, Lingling Wang* and Qiuju Zhou

*College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang, Henan 464000, China, Email: lintangxynu.edu.cn, xuepingchangxynu.edu.cn, wfulful163.com

L. Tang, G. Lv, Y. Fu, X.-P. Chang, R. Cheng, L. Wang, Q. Zhou, J. Org. Chem., 2022, 87, 14763-14777.

DOI: 10.1021/acs.joc.2c02093

---

see article for more reactions

Abstract

A simple and efficient 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted Heck-type alkene perfluoroalkylation of alkenes with perfluoroalkyl iodides in good yields proceeds smoothly via a radical process under visible light irradiation in the absence of an additional photocatalyst in ethyl acetate as a green solvent. DBU acts as both a halogen bond acceptor and a base.

see article for more examples

proposed mechanism

---

---

Key Words

perfluoroalkylation, alkenylation, photochemistry

---

ID: J42-Y2022