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Recent studies on the developments of the metal-catalyzed new borylation reactions by bis-(pinacolato)diboron (1) are described. The 1, 4-addition of 1 to a,/3-unsaturated carbonyl compoundsand nitriles proceeds in the presence of a catalytic amount of CuCl and KOAc in DMF.Subsequent treatment of the reaction mixture with water produces /3-boryl ketones, aldehydes,esters, and nitriles. Vinyl- and allylboron compounds are also obtained by the reactions of 1 withalkynes or allyl halides when using a stoichiometric amount of CuCl and KOAc. The aromaticC-H borylation of arenes or heteroarenes by 1 is effectively catalyzed by a combination of 1/2[Ir(OMe) (COD)] 2 and 4, 4'-di-tert-butyl-2, 2'-bipyridine in hexane. The high activity of the catalystallows the formation of aryl- and heteroarylboron compounds in high yields at room temperaturefrom equimolar equivalents of 1 and substrate. The direct borylation of alkylarenes by 1 catalyzedby Pd/C exclusively occurs via benzylic C-H activation to give benzylboron compounds

Developments of New Catalytic Borylation Reactions Directed towards Fine Organic Synthesis