Application of a ferrocene-based palladacycle precatalyst to enantioselective aryl-aryl Kumada coupling

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Arthurs, Ross A., Hughes, David L. and Richards, Christopher J. (2022) Application of a ferrocene-based palladacycle precatalyst to enantioselective aryl-aryl Kumada coupling. European Journal of Inorganic Chemistry, 2022 (9). ISSN 1434-1948

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Abstract

The palladium catalysed reaction of 1-iodo-2-methylnaphthalene and 2-methyl-1-naphthylmagnesium bromide gave quantitatively an ( S a )-configured cross-coupled product in 80% e.e. using ( R , S p )-PPFA as a ligand. N , N -Dimethylaminomethylferrocene was cyclopalladated (Na 2 PdCl 4 , ( S )-Ac-Phe-OH, 93% e.e., as determined by 1 H NMR as a result of self-induced non-equivalence), and the resulting ( S p )-configured dimeric palladacycle was employed as a precatalyst for this cross-coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base-promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an ( S p )-configured product in up to 71% e.e.

Item Type:	Article
Uncontrolled Keywords:	cross-coupling,enantioselectivity,ferrocene,ligand effects,palladacycles,inorganic chemistry,3* ,/dk/atira/pure/subjectarea/asjc/1600/1604
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	09 Feb 2022 17:30
Last Modified:	06 Feb 2025 10:24
URI:	https://ueaeprints.uea.ac.uk/id/eprint/83388
DOI:	10.1002/ejic.202101077

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