Palladium(II)-catalyzed ortho-arylation via phosphate-group-directed CaH activation

Aryl dialkyl phosphate, which is readily available from phenol, was a good substrate for the Pd(II) catalyzed arylaaryl coupling reaction through ortho-CaH activation. Although a phosphate group is regarded as a poor coordinating group, highly regioselective ortho-arylation could be achieved by empl...

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Bibliographic Details
Published in:Tetrahedron 2013-06, Vol.69 (25), p.5152-5159
Main Authors: Jeon, Woo, Lee, Tae, Kim, Eun, Moon, Bongjin, Kang, Jahyo
Format: Article
Language:English
Subjects:
Activation
Aromatic compounds
Bonding
Chemical reactions
Cleavage
Joining
Phosphates
Tetrahedrons
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Summary:Aryl dialkyl phosphate, which is readily available from phenol, was a good substrate for the Pd(II) catalyzed arylaaryl coupling reaction through ortho-CaH activation. Although a phosphate group is regarded as a poor coordinating group, highly regioselective ortho-arylation could be achieved by employing Pd(OTf)2ADT2H2O and Ar2IOTf as a catalyst and an aryl group source, respectively. The phosphate group of the resulting coupled product can be transformed into an aryl anion via reductive cleavage and used for further CaC bond formation.
ISSN:0040-4020
DOI:10.1016/j.tet.2013.04.067