Much effort has been devoted to transition-metal-catalyzed transformations of organoboronic acids in synthetic organic chemistry, since such boron-based organic synthesis often shows high stereo-, regio-, and chemoselectivities along with high reaction efficiency.  Herein, our recent findings on transition-metal-catalyzed synthesis and reactions of organoboronic acids are discussed.   Particular focus is on the ortho-functionalization of organoboronic acids with use of anthranilamide (AAM) as a removable ortho-directing group on the boron atom.  Application of the AAM-modified boronic acids to the sequence-selective synthesis of ortho-linked oligoarenes is also described.  Another major topic is stereospecific Suzuki�Miyaura cross coupling of a-aminobenzylboronic acid derivatives.  The reaction proceeds with inversion or retention of stereochemistry at the boron-bound stereogenic carbon centers, depending on the acidic additives used in the reaction.  New catalytic C-H borylation reactions may also be mentioned.

Selective organic synthesis via boron-based transition metal catalysis

244th National Meeting (2012)

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