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Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity

Cini, Melchior; Bradshaw, Tracey D.; Lewis, William; Woodward, Simon

Authors

Melchior Cini

Tracey D. Bradshaw

William Lewis

SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry



Abstract

The copper-catalysed (10 mol-% CuBr·SMe2, CuCN·LiCl or CuI/PPh3) addition of RMgBr to the pentafulvene 1-(cyclopenta-2,4-dien-1-ylidenemethyl)-2-methoxybenzene allows the formation of cyclopentadienyl derivatives with α-CHR(2-MeOPh) sidechains (R = Me, Et, nBu, iBu, allyl, Ph) without H– transfer. The deprotonation of these sec-alkyl-substituted cyclopentadienyls followed by the addition of TiCl4 allows the isolation of TiCl2{η5-C5H4CHR(2-OMePh)} as rac/meso mixtures that show activity against human colon, breast and pancreatic cell lines (GI50 2.3–42.4 μM).

Citation

Cini, M., Bradshaw, T. D., Lewis, W., & Woodward, S. (2013). Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity. European Journal of Organic Chemistry, 2013(19),

Journal Article Type Article
Online Publication Date May 15, 2013
Publication Date Jun 19, 2013
Deposit Date Jun 24, 2014
Publicly Available Date Jun 24, 2014
Journal European Journal of Organic Chemistry
Print ISSN 1434-193X
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2013
Issue 19
Public URL http://eprints.nottingham.ac.uk/id/eprint/3200
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300474/abstract
Related Public URLs http://www.interscience.wiley.com/
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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