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Room-temperature palladium-catalyzed C-H activation: ortho-carbonylation of aniline derivatives.

Angewandte Chemie (International ed. in English) (2009-01-27)
Chris E Houlden, Marc Hutchby, Chris D Bailey, J Gair Ford, Simon N G Tyler, Michel R Gagné, Guy C Lloyd-Jones, Kevin I Booker-Milburn
RESUMEN

Pd and CO--ureally got me! The title reaction proceeds efficiently at 18 degrees 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).

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Sigma-Aldrich
Methyl anthranilate, ≥98%, FCC, FG
Sigma-Aldrich
Methyl anthranilate, ReagentPlus®, ≥99%