Issue 35, 2014
From the journal:

Chemical Communications

Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions†

Michaela Mühlberg,ab   Kristina D. Siebertz,bc   Brigitte Schlegel,b   Peter Schmiederb  and  Christian P. R. Hackenberger*bc  

* Corresponding authors

a Freie Universität Berlin, Institut für Chemie und Biochemie, Takustr. 3, 14195 Berlin, Germany

b Forschungsinstitut für Molekulare Pharmakologie (FMP), Robert-Roessle-Str. 10, 13125 Berlin, Germany
E-mail: hackenbe@fmp-berlin.de
Fax: +49 (0)30 947931

c Humboldt Universität zu Berlin, Institut für Organische und Bioorganische Chemie, Institut für Chemie, Brook-Taylor-Str. 2, 12489 Berlin, Germany

Abstract

The thioacid–azide reaction and its chemoselectivity were probed with alkyl azides for a potential application to form amide bonds in aqueous solvents. Our results reveal that under acidic conditions thioamides were formed as major reaction products suggesting a competing mechanism, whereas reactions forming amides predominated at slightly higher pH values.

Graphical abstract: Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions

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Article information

DOI
https://doi.org/10.1039/C4CC00774C
Article type
Communication
Submitted
28 Jan 2014
Accepted
12 Mar 2014
First published
12 Mar 2014

Chem. Commun., 2014,50, 4603-4606

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Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions

M. Mühlberg, K. D. Siebertz, B. Schlegel, P. Schmieder and C. P. R. Hackenberger, Chem. Commun., 2014, 50, 4603 DOI: 10.1039/C4CC00774C

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