180690-91-9Relevant articles and documents
Room-temperature palladium-catalyzed C-H activation: Ortho-carbonylation of aniline derivatives
Houlden, Chris E.,Hutchby, Marc,Bailey, Chris D.,Ford, J.Gair,Tyler, Simon N. G.,Gagne, Michel R.,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.
supporting information; experimental part, p. 1830 - 1833 (2009/08/07)
Pd and CO - ureally got me! The title reaction proceeds efficiently at 18°C under CO (1 atm) with 5 % [Pd(OTs)2 (MeCN)2] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ=benzoquinone, Ts=4-toluenesulfonyl).
Optional site selectivity in the metalation of o- and p-anisidine through matching of reagents with neighboring groups
Maggi, Raimondo,Schlosser, Manfred
, p. 5430 - 5434 (2007/10/03)
N-Protected o- and p-anisidines (2- and 4-methoxyanilines) undergo a hydrogen/metal exchange at the position adjacent to either the oxygen or nitrogen atom depending on what organometalic base is employed. These synthetically useful findings support previous views about neighboring group/reagent interactions.