Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202307581
Keywords
C-H Activation; Heterobiaryl; Olefination; Palladium; Site-Selectivity
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Remote C-H functionalization of heterocyclic biaryls is crucial in synthesis and medicinal chemistry. New catalytic templates have been developed to functionalize the hindered ortho-C-H bonds of heterobiaryls, using directing heteroatom at the meta- or para-positions, with unprecedented site-selectivity. This protocol overcomes steric and electronic effects, allowing olefination of sterically hindered heterobiaryls.
Remote C-H functionalization of heterocyclic biaryls will be of great importance in synthesis and medicinal chemistry. Through adjusting the geometric relationship of the directing atom and target C-H bonds, two new catalytic templates have been developed to enable the functionalization of the more hindered ortho-C-H bonds of heterobiaryls bearing directing heteroatom at the meta- or para-positions, affording unprecedented site-selectivity. The use of template chaperone also overcomes product inhibition and renders the directing templates catalytic. The utility of this protocol was demonstrated by olefination of heterocyclic biaryls with various substituents, overriding conventional steric and electronic effects. These ortho-C-H olefinated heterobiaryls are sterically hindered and can often be challenging to prepare through aryl-aryl coupling reactions.
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