Herein, we report the development of ruthenium-catalysed cross-coupling reaction of β-ketoamides as alkenyl electrophiles with organoboronates. This reaction presumably proceeds the cleavage of the alkenyl C-N bond of the β-enaminoamide, which is generated from the β-ketoamide and pyrrolidine, and is promoted by a nearby amide directing group and a ruthenium catalyst.
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http://dx.doi.org/10.1039/d3cc04265k | DOI Listing |
Chem Commun (Camb)
October 2023
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Technology, Hachioji, Tokyo 192-0982, Japan.
Nat Chem
September 2021
Department of Chemistry, University of Chicago, Chicago, IL, USA.
While metathesis reactions involving carbon-carbon double bonds, namely olefin metathesis, have been well established with broad utility in organic synthesis and materials science, direct metathesis of kinetically less accessible C-C single bonds is extremely rare. Here we report a ruthenium-catalysed reversible C-C single-bond metathesis reaction that allows redox- and pH-neutral biaryl synthesis. Assisted by directing groups, unstrained homo-biaryl compounds undergo aryl exchanges to generate cross-biaryl products, catalysed by a well-defined air-stable ruthenium(II) complex.
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March 2017
School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, Perth 6009, Western Australia, Australia.
Two new N-heterocyclic carbene (NHC) ligands bearing 2-morpholino and 2-piperidinyl naphthyl wingtips were synthesised (2-SIMorNap and 2-SIPipNap). Nuclear magnetic resonance studies, in conjunction with crystal structures and derivatisation of the NHC salts using a chiral counteranion, revealed that the ligand wingtips are oriented anti with respect to each other. From the free carbene, palladium, ruthenium and iridium complexes were prepared.
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