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Pure Appl. Chem., 2006, Vol. 78, No. 7, pp. 1369-1375

Iridium-catalyzed borylation of arenes and heteroarenes via C-H activation

Tatsuo Ishiyama and Norio Miyaura

Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan

Abstract: Direct C-H borylation of aromatic compounds catalyzed by a transition-metal complex was studied as an economical protocol for the synthesis of aromatic boron derivatives. Iridium complexes generated from Ir(I) precursors and 2,2'-bipyridine ligands efficiently catalyzed the reactions of arenes and heteroarenes with bis(pinacolato)diboron or pinacolborane to produce a variety of aryl- and heteroarylboron compounds. The catalytic cycle involves the formation of a tris(boryl)iridium(III) species and its oxidative addition to an aromatic C-H bond.