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. (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

[img]
Preview
PDF (EJIC18-1655) - Submitted Version
Download (464kB) | Preview

    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
    Related URLs:
    Depositing User: LivePure Connector
    Date Deposited: 04 Feb 2019 16:30
    Last Modified: 11 Apr 2019 16:03
    URI: https://ueaeprints.uea.ac.uk/id/eprint/69840
    DOI: 10.1002/ejic.201800129

    Actions (login required)

    View Item