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Isodesmic C–H Functionalization: Carboxyl-Assisted Remote meta- and ortho-C–H Iodination of Arenes via Shuttle Catalysis

submitted on 19.04.2021, 18:15 and posted on 20.04.2021, 12:56 by Shangda Li, Chunhui Zhang, Lei Fu, Hang Wang, Lei Cai, Xiaoxi Chen, Xinchao Wang, Gang Li
Isodesmic C–H functionalization reactions are extremely rare. Herein we report the first Pd(II)-catalyzed isodesmic C–H iodination of arenes using 2-nitrophenyl iodides as the mild iodinating reagents. Unusual C–I reductive elimination occurred in preference to competing C–C coupling in this reaction. Assisted by aliphatic carboxyl directing groups, a range of hydrocinnamic acids and related arenes could be selectively iodinated at either meta- or ortho-positions of the phenyl ring. Remote diastereoselective C–H activation was also promising. This method may open up a new way to iodinate challenging substrates.


Email Address of Submitting Author


Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no conflict of interest.