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

Katrine Qvortrup | Zendy; Rico Petersen | Zendy; Asmus Ougaard Dohn | Zendy; Klaus B. Møller | Zendy; Thomas E. Nielsen | Zendy

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

Author(s) -

Katrine Qvortrup,

Rico Petersen,

Asmus Ougaard Dohn,

Klaus B. Møller,

Thomas E. Nielsen

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01386

Subject(s) - chemistry , chemoselectivity , hydroxylamine , linker , hydroxamic acid , solvent , photodissociation , combinatorial chemistry , organic chemistry , catalysis , computer science , operating system

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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