Multiple acetylation of pentaphenylferrocene – Synthesis and asymmetric reduction of 1-acetyl-1′,2′,3′,4′,5′-penta(para‐acetylphenyl)ferrocene

Arthurs, Ross A. and Richards, Christopher J. ORCID: https://orcid.org/0000-0001-7899-4082 (2018) Multiple acetylation of pentaphenylferrocene – Synthesis and asymmetric reduction of 1-acetyl-1′,2′,3′,4′,5′-penta(para‐acetylphenyl)ferrocene. European Journal of Inorganic Chemistry, 2018 (15). pp. 1655-1659. ISSN 1434-1948

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Abstract

The Friedel–Crafts acetylation of pentaphenylferrocene has been revisited using 1.1 equivalents of AcCl/AlCl3 in CH2Cl2 at room temperature leading to the synthesis of 1‐acetyl‐1′,2′,3′,4′,5′‐pentaphenylferrocene (78 % yield). Increased quantities of reagents and longer reaction times resulted in acetylation of the phenyl groups exclusively at the para‐position, this methodology culminating in the synthesis of 1‐acetyl‐1′,2′,3′,4′,5′‐penta(para‐acetylphenyl)ferrocene (32 % for a two step process). Subsequent asymmetric reduction of all six ketone functionalities with BH3·SMe2 catalysed by 60 mol‐% (S)‐CBS proceeded in 81 % yield to give (R,R,R,R,R,R)‐1‐(α‐hydroxyethyl)‐1′,2′,3′,4′,5′‐penta[para‐(α‐hydroxyethyl)phenyl]ferrocene, a highly functionalised enantiopure building block for the synthesis of ligands and materials.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User: LivePure Connector
Date Deposited: 04 Feb 2019 16:30
Last Modified: 22 Oct 2022 04:27
URI: https://ueaeprints.uea.ac.uk/id/eprint/69840
DOI: 10.1002/ejic.201800129

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