Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes

Phillips, D., Hewitt, J. F.M. and France, D. (2018) Synthesis of 3,3-disubstituted heterocycles by Pd-catalyzed arylallylation of unactivated alkenes. ACS Omega, 3(7), pp. 8451-8459. (doi: 10.1021/acsomega.8b01021)

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Finding new methods of carbon–carbon bond formation is a key goal in expanding current methodology for heterocycle formation. Because of their inherently non-planar shape, new methods of forming sp3-rich scaffolds are of particular importance. While there are methods for combining heterocyclisation and formation of new sp3–sp3 carbon–carbon bonds, these form the carbon– heteroatom bond rather than a carbon–carbon bond of the heterocycle. Here we show a new alkene arylallylation reaction that generates a heterocycle with concomitant formation of two new carbon– carbon bonds. Furthermore, we demonstrate that this process occurs through an isohypsic (redox neutral) mechanism. Overall, this carboallylation reaction gives a new route to the synthesis of 3,3- disubstituted heterocycles.

Item Type:Articles
Glasgow Author(s) Enlighten ID:France, Dr David and Phillips, Mr David
Authors: Phillips, D., Hewitt, J. F.M., and France, D.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:ACS Omega
Publisher:American Chemical Society
ISSN (Online):2470-1343
Copyright Holders:Copyright © 2018 American Chemical Society
First Published:First published in ACS Omega 3(7):8451-8459
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 and Physical Sciences Research Council (EPSRC)EP/I027165/1CHEM - CHEMISTRY