Solvent-Controlled Chemoselectivity in the Photolytic Release of Hydroxamic Acids and Carboxamides from Solid Support

Katrine Qvortrup; Rico G Petersen; Asmus Ougaard Dohn; Klaus Braagaard Møller; Thomas E Nielsen

doi:10.1021/acs.orglett.7b01386

Solvent-Controlled Chemoselectivity in the Photolytic Release of Hydroxamic Acids and Carboxamides from Solid Support

Katrine Qvortrup, Rico G Petersen, Asmus Ougaard Dohn, Klaus Braagaard Møller, Thomas E Nielsen

Department of Chemistry

Technical University of Denmark

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Abstract

The synthetic utility and theoretical basis of a photolabile hydroxylamine-linker are presented. The developed protocols enable the efficient synthesis and chemoselective photolytic release of either hydroxamates or carboxamides from solid support. The bidetachable mode of the linker unit is uniquely dependent on the solvent. Hydroxamic acids are obtained by performing photolysis in protic solvents, whereas photolysis in aprotic solvents enables the selective release of carboxamides.

Original language	English
Journal	Organic Letters
Volume	19
Issue number	12
Pages (from-to)	3263-3266
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/acs.orglett.7b01386
Publication status	Published - 2017

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abstract = "The synthetic utility and theoretical basis of a photolabile hydroxylamine-linker are presented. The developed protocols enable the efficient synthesis and chemoselective photolytic release of either hydroxamates or carboxamides from solid support. The bidetachable mode of the linker unit is uniquely dependent on the solvent. Hydroxamic acids are obtained by performing photolysis in protic solvents, whereas photolysis in aprotic solvents enables the selective release of carboxamides.",

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AU - Qvortrup, Katrine

AU - Petersen, Rico G

AU - Dohn, Asmus Ougaard

AU - Møller, Klaus Braagaard

AU - Nielsen, Thomas E

PY - 2017

Y1 - 2017

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AB - The synthetic utility and theoretical basis of a photolabile hydroxylamine-linker are presented. The developed protocols enable the efficient synthesis and chemoselective photolytic release of either hydroxamates or carboxamides from solid support. The bidetachable mode of the linker unit is uniquely dependent on the solvent. Hydroxamic acids are obtained by performing photolysis in protic solvents, whereas photolysis in aprotic solvents enables the selective release of carboxamides.

U2 - 10.1021/acs.orglett.7b01386

DO - 10.1021/acs.orglett.7b01386

M3 - Journal article

C2 - 28570068

SN - 1523-7060

VL - 19

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EP - 3266

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Solvent-Controlled Chemoselectivity in the Photolytic Release of Hydroxamic Acids and Carboxamides from Solid Support

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