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New Transformations of Secondary Alkylboronic Esters

"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 f... ver más

28/02/2013

UNIVERSITY OF BRIS...

209K€

Presupuesto del proyecto: 209K€

Líder del proyecto

UNIVERSITY OF BRISTOL No se ha especificado una descripción o un objeto social para esta compañía.

TRL 4-5

Fecha límite participación Sin fecha límite de participación.

Financiación concedida El organismo FP7 notifico la concesión del proyecto el día 2013-02-28 No tenemos la información de la convocatoria

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1 Participantes

UNIVERSITY OF BRISTOL

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Líder del proyecto

UNIVERSITY OF BRISTOL No se ha especificado una descripción o un objeto social para esta compañía.

TRL 4-5

Presupuesto del proyecto 209K€

Fecha límite de participación Sin fecha límite de participación.

Descripción del proyecto "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."

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