Boron linkers and immobilised Boranes for solid phase chemistry
Boron linkers and immobilised Boranes for solid phase chemistry
This thesis describes the synthesis and evaluation of two linkers designed for the immobilisation of boronic acids onto the solid phase. Solution hydroboration with catecholborane and derivatisation of the resultant boronate esters was carried out.
A linker with a catechol functionality was synthesised and attached to the solid phase. Initial attempts to couple this linker resulted in aminomethyl resin, but the coupling was subsequently achieved in good yield.
Conversion of this linker to a solid supported catecholborane and subsequent solid phase hydroboration was attempted. A solid supported boronate was also synthesised by the condensation of the catechol resin and a boronic acid.
A linker with a 1,2-diol functionality was synthesised on the solid phase. Conversion of this linker to the pinacol-type-borane and subsequent hydroboration was attempted. A number of boronic acids were coupled to the glycol resin by condensation. Solution hydrocarbon with catecholborane yielded a number of catecholboronate esters that were coupled to the glycol resin by transesterification. The resin bound boronates were cleaved from the resin by an electrophilic oxidative method to yield boronic acids, a nucleophilic oxidative method to give phenols, an aldehyde, an alcohol and a ketone and Suzuki couplings which led to a biphenyl.
University of Southampton
Sampson, David Francis John
2002
Sampson, David Francis John
Sampson, David Francis John
(2002)
Boron linkers and immobilised Boranes for solid phase chemistry.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
This thesis describes the synthesis and evaluation of two linkers designed for the immobilisation of boronic acids onto the solid phase. Solution hydroboration with catecholborane and derivatisation of the resultant boronate esters was carried out.
A linker with a catechol functionality was synthesised and attached to the solid phase. Initial attempts to couple this linker resulted in aminomethyl resin, but the coupling was subsequently achieved in good yield.
Conversion of this linker to a solid supported catecholborane and subsequent solid phase hydroboration was attempted. A solid supported boronate was also synthesised by the condensation of the catechol resin and a boronic acid.
A linker with a 1,2-diol functionality was synthesised on the solid phase. Conversion of this linker to the pinacol-type-borane and subsequent hydroboration was attempted. A number of boronic acids were coupled to the glycol resin by condensation. Solution hydrocarbon with catecholborane yielded a number of catecholboronate esters that were coupled to the glycol resin by transesterification. The resin bound boronates were cleaved from the resin by an electrophilic oxidative method to yield boronic acids, a nucleophilic oxidative method to give phenols, an aldehyde, an alcohol and a ketone and Suzuki couplings which led to a biphenyl.
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Published date: 2002
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Local EPrints ID: 464796
URI: http://eprints.soton.ac.uk/id/eprint/464796
PURE UUID: 697d3ba8-8a8c-45e1-a358-15b1599e7813
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Date deposited: 05 Jul 2022 00:02
Last modified: 05 Jul 2022 00:02
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Author:
David Francis John Sampson
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