Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity
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. T...
| Main Authors: | , , , |
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| Format: | Article |
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Wiley-VCH Verlag
2013
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| Online Access: | https://eprints.nottingham.ac.uk/3200/ |
| _version_ | 1848790975678251008 |
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| author | Cini, Melchior Bradshaw, Tracey D. Lewis, William Woodward, Simon |
| author_facet | Cini, Melchior Bradshaw, Tracey D. Lewis, William Woodward, Simon |
| author_sort | Cini, Melchior |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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). |
| first_indexed | 2025-11-14T18:21:09Z |
| format | Article |
| id | nottingham-3200 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T18:21:09Z |
| publishDate | 2013 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-32002020-05-04T16:37:14Z https://eprints.nottingham.ac.uk/3200/ 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 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). Wiley-VCH Verlag 2013-06-19 Article PeerReviewed 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 http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300474/abstract |
| spellingShingle | Cini, Melchior Bradshaw, Tracey D. Lewis, William Woodward, Simon Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| title | Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| title_full | Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| title_fullStr | Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| title_full_unstemmed | Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| title_short | Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| title_sort | cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity |
| url | https://eprints.nottingham.ac.uk/3200/ https://eprints.nottingham.ac.uk/3200/ |