Aerobic Copper-Catalyzed Salicylaldehydic C formyl -H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed C -H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the C -H bond compared to the...

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Bibliographic Details
Published in:Chemistry : a European journal 2021-02, Vol.27 (10), p.3278-3283
Main Authors: Xiao, Lin, Lang, Tao-Tao, Jiang, Ying, Zang, Zhong-Lin, Zhou, Cheng-He, Cai, Gui-Xin
Format: Article
Language:English
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Summary:We report a challenging copper-catalyzed C -H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the C -H bond compared to the phenolic O-H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a Cu /Cu /Cu catalytic cycle.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202004810