Isodesmic C–H Functionalization: Carboxyl-Assisted Remote meta- and ortho-C–H Iodination of Arenes via Shuttle Catalysis
2021
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.
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