TASTE
New Transformations of Secondary Alkylboronic Esters
| Coordinatore | UNIVERSITY OF BRISTOL
Organization address
address: TYNDALL AVENUE SENATE HOUSE contact info |
| Nazionalità Coordinatore | United Kingdom [UK] |
| Totale costo | 209˙092 € |
| EC contributo | 209˙092 € |
| Programma | FP7-PEOPLE
Specific programme "People" implementing the Seventh Framework Programme of the European Community for research, technological development and demonstration activities (2007 to 2013) |
| Code Call | FP7-PEOPLE-2010-IEF |
| Funding Scheme | MC-IEF |
| Anno di inizio | 2011 |
| Periodo (anno-mese-giorno) | 2011-03-01 - 2013-02-28 |
Partecipanti
| # | ||||
|---|---|---|---|---|
| 1 |
UNIVERSITY OF BRISTOL
Organization address
address: TYNDALL AVENUE SENATE HOUSE contact info |
UK (BRISTOL) | coordinator | 209˙092.80 |
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Obiettivo del progetto (Objective)
'The properties of organic molecules are defined by their shape and functionality. However, the creation of such molecules with control over both of these features is highly challenging. This proposal describes novel methodology for simultaneous C-C bond formation with control over shape (stereochemistry). In particular it focuses on the stereoselective replacement of boron (which is easy to introduce) to halides and other heteroatoms, and new ways for cross-coupling to aromatics without the need for transition metals.
In order to promote the electrophilic halogenation of a boronic ester, we envisaged the reaction of boronate complex with a halogen electrophile. In preliminary experiments such processes have already been found to be viable and occur with complete stereoinversion. Through tuning the nature of the aryl lithium one could envisage selective halogenation of a broad range of substrates, giving access to a myriad of stereodefined secondary alkyl halides, including fluorides. Moreover, alcohols, amines derivatives, thioethers and selenoethers could all be accessible by the reaction of these new activated boronic ester ate complexes with suitable electrophiles.
The final part will focus on the (transition metal-free) cross coupling of secondary alkylboronic esters. We present a conceptually new approach to this challenging problem by considering the reaction of a secondary boronic ester with an aryl lithium reagent. Following ate complex formation, one-electron oxidation would result in dearomatization leading to a radical cation which would trigger a 1,2-migration/rearomatization sequence. High stereointegrity can be expected for such a process from the stereospecificity of the 1,2-sigmatropic rearrangement. Preliminary results have shown that the concept is again viable but needs substantial optimization. This methodology will be applied to challenges in synthesis.'