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Updated: Jun 6, 2025
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Metal-Catalyzed Hydrogen Atom Transfer (MHAT) Hydroalkylation with Electron-Deficient Alkynes
Laura G Rodríguez1, Josep Bonjoch1, Ben Bradshaw1
1Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Barcelona 08028, Spain.
Abstract:
We present a novel strategy for olefin construction via the reductive coupling of electron-neutral alkenes with electron-deficient alkynes under metal-catalyzed hydrogen atom transfer conditions. This methodology provides selective access to both trans and the more challenging-to-synthesize cis isomers and permits the olefin to be installed next to sterically hindered centers, key factors in the synthesis of biologically active compounds. The reaction exhibits broad functional group tolerance and proceeds under mild, nontoxic conditions with high atom efficiency.
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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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