Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O-Benzoyl-N,N-dialkylhydroxylamines

Naoki Matsuda, Koji Hirano*, Tetsuya Satoh and Masahiro Miura*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: k_hiranochem.eng.osaka-u.ac.jp, miurachem.eng.osaka-u.ac.jp

N. Matsuda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc., 2013, 135, 4934-4937.

DOI: 10.1021/ja4007645

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Abstract

A Cu-catalyzed regioselective and stereospecific aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines delivers β-aminoalkylboranes in good yields. The Cu catalysis enables introduction of both amine and boron moieties to C-C double bonds simultaneously in a syn fashion. Moreover, the use of a chiral biphosphine ligand, (S,S)-Me-Duphos, provides optically active β-aminoalkylboranes.

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Key Words

benzylic amines, alkylboronates, multicomponent reactions

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ID: J48-Y2013-0840