A decarboxylative cross-coupling of 3-substituted picolinic acids with (hetero)aryl halides is presented. In the presence of catalytic CuO and Pd(1,5-cyclooctadiene)Cl with 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl as the ligand, both electron-rich and electron-deficient aryl bromides and chlorides as well as heteroaryl bromides were successfully coupled with various picolinate salts under mild conditions in yields up to 96%. This protocol provides an efficient entry to 2-(hetero)arylpyridines, an attractive substance class in drug discovery.

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http://dx.doi.org/10.1021/acs.joc.7b00046DOI Listing

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