Organic Chemistry Portal

Abstracts

Search:

Visible-Light-Triggered Iodinations Facilitated by Weak Electrostatic Interaction of N-Heterocyclic Carbenes

He Sheng, Qiang Liu, Xiao-Di Su, Yu Lu, Zhi-Xiang Wang* and Xiang-Yu Chen*

*School of Chemical Sciences, University of the Chinese Academy of Sciences, Beijing 100049, China, Email: zxwangucas.ac.cn, chenxiangyu20ucas.ac.cn

H. Sheng, Q. Liu, X.-D. Su, Y. Lu, Z.-X. Wang, X.-Y. Chen, Org. Lett., 2020, 22, 7187-7192.

DOI: 10.1021/acs.orglett.0c02523 (free Supporting Information)


see article for more reactions

Abstract

By utilizing N-heterocyclic carbenes as stabilizer through electrostatic interaction rather than electron donation, a visible-light-triggered radical-radical cross-coupling of N-alkenoxypyridinium salts and NaI provides a variety of α-iodo ketones.

see article for more examples

proposed mechanism



Key Words

α-Iodoketones, Organocatalysis, Photochemistry


ID: J54-Y2020