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Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes

Cleghorn, L.A.T., Grigg, R., Savic, V. and Simic, M. (2008) Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes. Tetrahedron, 64 (37). pp. 8731-8738. ISSN 0040-4020

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Abstract

Allylation of α,β-unsaturated aldehydes and cyclic ketones promoted by Pd/In transmetallation processes has been studied. The unsaturated aldehydes underwent regioselective 1,2-addition to afford secondary homoally alcohols. The reactions have been performed using Pd(OAc)2/PPh3 as catalytic system and metallic indium affording the products in good yields. The same transformation with unsaturated ketones proved to be less efficient, while saturated cyclic ketones delivered generally excellent yields in the presence of CuI. In these latter processes the presence of a distal heteroatom influences the reaction rate.

Item Type: Article
Copyright, Publisher and Additional Information: © 2008 Elsevier B.V. This is an author produced version of a paper published in Tetrahedron. Uploaded in accordance with the publisher's self archiving policy.
Institution: The University of Leeds
Academic Units: The University of Leeds > Faculty of Maths and Physical Sciences (Leeds) > School of Chemistry (Leeds)
Depositing User: Sherpa Assistant
Date Deposited: 09 Oct 2008 10:56
Last Modified: 08 Feb 2013 16:56
Published Version: http://dx.doi.org/10.1016/j.tet.2008.06.100
Status: Published
Publisher: Elsevier B.V.
Identification Number: 10.1016/j.tet.2008.06.100
URI: http://eprints.whiterose.ac.uk/id/eprint/4734

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