Journal of the American Chemical Society · 2010 · 258 citations · 61 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistryCoordination ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAryl Halide CouplingCross-coupling CatalysisDecarboxylative CouplingDecarboxylative Cross-couplingPalladium-catalyzed Cross-couplingStereoselective Cross-couplingTransition-metal-catalyzed Cross-couplingTransition-metal-catalyzed Heterocycle Synthesis
Pd-catalyzed decarboxylative cross-couplings of 2-(2-azaaryl)acetates with aryl halides and triflates have been discovered. This reaction is potentially useful for the synthesis of some functionalized pyridines, quinolines, pyrazines, benzoxazoles, and benzothiazoles. Theoretical analysis shows that the nitrogen atom at the 2-position of the heteroaromatics directly coordinates to Pd(II) in the decarboxylation transition state.
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Synthesis of Biaryls via Catalytic Decarboxylative Coupling
Lukas J. Gooßen, Guo‐Jun Deng, Laura M. Levy · Science · 2006 · 946 citations