An efficient copper-catalyzed coupling reaction of pyridin-2-ones with aryl and heterocyclic halides based on Buchwald's protocol (original) (raw)
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ChemInform, 2009
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Tetrahedron Letters, 1999
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Substrate-Directed C-H Functionalization of 2-Aryl Pyridines by Transition Metal Complexes
ChemistrySelect, 2018
Transition metal mediated CÀH activation is a powerful synthetic tool for the total synthesis of complex natural products and biologically active molecules. The strategy involves mainly CÀH activation, nucleophilic addition and regeneration of the catalyst. It proceeds through a CÀH bond cleavage by ligand coordination to transition metal. Transition metals like Pd, Rh, Ru, Co, and Ir are the most often used catalysts, which form a complex with 2-aryl pyridine and facilitates the functionalization of various CÀH bonds to generate diverse CÀC and CÀX bonds under typically mild reaction conditions with low catalyst loading. In particular, the chelation-assisted cleavage of CÀH bonds at ortho-position of the pyridine directing group has been recognized as one of the most powerful strategies for the functionalization of unreactive CÀH bonds. Recently, transition metal catalyzed CÀH bond activation has received significant interest because it does not require the prefunctionalization of the substrate. Therefore, the metal-catalyzed CÀH activation and functionalization is currently considered as atom economy and simplified procedure in comparison with the traditional strategies. Recent years have witnessed remarkable progress in the development of more atom-and step-economical direct arylations of 2-aryl pyridines. In 2008, Nakamura et al reported a new class of homogeneous iron-catalyzed arylation of 2-aryl pyridines by a C À H bond activation (Scheme 1). [16] The overall synthetic transformation represents a nucleophilic displacement of ortho CÀH bond of 2-aryl pyridine (3) by an arylzinc bromide (4) to give the arylated product (5) in good yield. The reaction took place at 0 8C since C À H bond activation often requires high temperature above 80 8C. The direct crosscoupling reaction of 2-aryl pyridines with Grignard reagent through Co catalyst also well established. [17] Authors observed that the combination of iron, zinc, magnesium, 1,10-phenan-[a] Dr.