Palladium-catalyzed heteroallylation of unactivated alkenes – synthesis of citalopram

Hewitt, J.F.M., Williams, L., Aggarwal, P., Smith, C.D. and France, D.J. (2013) Palladium-catalyzed heteroallylation of unactivated alkenes – synthesis of citalopram. Chemical Science, 4, pp. 3538-3543. (doi:10.1039/C3SC51222C)

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Abstract

A palladium-catalyzed difunctionalization of unactivated alkenes with tethered nucleophiles is reported. The versatile reaction occurs with simple allylic halides and can be carried out under air. The methodology provides rapid access to a wide array of desirable heterocyclic targets, as illustrated by a concise synthesis of the widely prescribed antidepressant citalopram.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:France, Dr David and Aggarwal, Dr Pooja
Authors: Hewitt, J.F.M., Williams, L., Aggarwal, P., Smith, C.D., and France, D.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Chemical Science
Publisher:Royal Society of Chemistry
ISSN:2041-6520
ISSN (Online):2041-6539
Copyright Holders:Copyright © 2013 The Royal Society of Chemistry
First Published:First published in Chemical Science 4:3568-3543
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
554061New Multiple Bond-Forming Strategies for Organic SynthesisDavid FranceEngineering & Physical Sciences Research Council (EPSRC)EP/I027165/1CHEM - CHEMISTRY
235244Donation to support high quality synthetic organic chemistry in the UKDavid ProcterPfizer Global Research and Development (PFIZER)UNSPECIFIEDCHEM - CHEMISTRY