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

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Cini, Melchior, Bradshaw, Tracey D., Lewis, William and Woodward, Simon (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). pp. 3997-4007. ISSN 1099-0690

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300474/abstract

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).

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Article

RIS ID:

https://nottingham-repository.worktribe.com/output/715614

Schools/Departments:

University of Nottingham, UK > Faculty of Science > School of Chemistry

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