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THE DEVELOPMENT OF METAL CATALYZED BENZANNULATION PROTOCOLS FOR THE SYNTHESIS OF AROMATIC BORONIC ESTERS

Auvinet, Anne Laure and Auvinet, Anne Laure (2011) THE DEVELOPMENT OF METAL CATALYZED BENZANNULATION PROTOCOLS FOR THE SYNTHESIS OF AROMATIC BORONIC ESTERS. PhD thesis, University of Sheffield.

[img] Text (PhD Thesis)
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Abstract

A transition metal catalyzed benzannulation of alkynylboronates and dienes/diene equivalents has been developed for the synthesis of aromatic boronic esters. Alkynylboronates participate in a regioselective cycloaddition with 1,3-butadiene derivatives, under ambient conditions in the presence of a cobalt catalyst. The methodology provides a convenient and general route to access 1,2-di-substituted, 1,2,3- or 1,3,4-tri-substituted and 1,2,3,4-tetra-substituted benzene based systems incorporating a boronate moiety. The newly formed aromatic boronic esters can undergo a Suzuki cross-coupling to afford functionalized aminopyridine derivatives. In addition, alkynylboronates participate in benzannulation reactions with cyclobutenones, at room temperature under nickel catalysis. The strategy provides an easy access to highly (tetra/penta) substituted phenol boronic ester derivatives in a remarkably regioselective manner. This chemistry offers an efficient route to quinone boronic esters, as well as the opportunity to carry out benzannulation and cross-coupling reactions in one-pot with a single pre-catalyst. To extend the general strategy, an alternative sequence that employs a palladium catalyzed cyclisation process involving o-alkynylanilines is terminated by a boration reaction to furnish the corresponding indole boronic ester derivatives.

Item Type: Thesis (PhD)
Additional Information: al.auvinet@voila.fr
Academic Units: The University of Sheffield > Faculty of Science (Sheffield) > Chemistry (Sheffield)
Depositing User: Miss Anne Laure Auvinet
Date Deposited: 30 Jan 2012 10:53
Last Modified: 08 Aug 2013 08:48
URI: http://etheses.whiterose.ac.uk/id/eprint/2027

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