Palladium(II)‐Catalyzed Dehydroboration via Generation of Boron Enolates |
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| Authors: | Dr Yuki Sakamoto Dr Toru Amaya Dr Takeyuki Suzuki Prof?Dr Toshikazu Hirao |
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| Institution: | 1. The Institute of Scientific and Industrial Research, Osaka University, Mihoga-oka, Ibaraki, Osaka, Japan;2. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, Japan |
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| Abstract: | The PdII‐catalyzed dehydroboration of boron enolates generated from ketones and 9‐iodo‐9‐borabicyclo3.3.1]nonane was achieved, providing a synthetically versatile protocol from ketones to α,β‐unsaturated ketones. The PdII compound employed in this reaction worked catalytically in the presence of Cu(OAc)2. The high trans‐selectivity of the olefinic moiety was observed. Aryl halide moieties (‐Br and ‐Cl) remained intact for this reaction in spite of the presence of a Pd species. An ester substrate could also be applied when a stoichiometric amount of PdII was used. The crossover reactions using boron and silyl enolates revealed that the oxidation reaction is much faster than the Saegusa‐Ito reaction. |
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| Keywords: | boron enolate dehydrogenation enones oxidation palladium |
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