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