Catalyzed hydroboration of nitrostyrenes and 4-vinylaniline: a mild and selective route to aniline derivatives containing boronate esters |
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Authors: | Christopher M Vogels Stephen A Westcott |
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Institution: | a Department of Chemistry, Mount Allison University, Sackville, NB, Canada E4L 1G8 b Department of Chemistry, University of New Brunswick, Fredericton, NB, Canada E3B 5A3 |
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Abstract: | Transition metal catalyzed reactions of catecholborane (HBcat; cat = 1,2-O2C6H4) with β-nitrostyrene and 3-nitrostyrene lead to products derived from competing hydrogenation and hydroboration of the alkene unit along with reduction of the nitro group. Hydroboration of 4-vinylaniline gave regioselective formation of either the branched or the linear organoboronate ester depending upon the catalyst precursors (i.e., RhCl(PPh3)3 or Rh(acac)(dppe) vs Cp∗IrCl2]2) used to facilitate this reaction. Hydroboration products were converted to air-stable primary amines by addition of pinacol. |
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Keywords: | Aminoboron Catalysis Hydroboration Regioselectivity |
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