Access to N-cyanosulfoximines by transition metal-free iminations of sulfoxides

C. A. Dannenberg; L. Fritze; F. Krauskopf; C. Bolm

doi:10.1039/C6OB02691E

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Access to N-cyanosulfoximines by transition metal-free iminations of sulfoxides†

C. A. Dannenberg,^a L. Fritze,^a F. Krauskopf^a and C. Bolm

*^a

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* Corresponding authors

^a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany
E-mail: carsten.bolm@oc.rwth-aachen.de
Fax: +49 241 80 92 391
Tel: +49 24 80 94 675

Abstract

A transition metal-free synthesis of N-cyanosulfoximines from sulfoxides using N-chlorosuccinimide (NCS) as oxidising agent and cyanamide as nucleophilic amine source is reported. The products are obtained in moderate to excellent yields. The protocol enables an easy access to N-cyanosulfoximines from readily available starting materials under inversion of configuration at a preexisting stereogenic center.

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Article information

DOI: https://doi.org/10.1039/C6OB02691E
Article type: Communication
Submitted: 09 Dec 2016
Accepted: 04 Jan 2017
First published: 04 Jan 2017

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Org. Biomol. Chem., 2017,15, 1086-1090

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Access to N-cyanosulfoximines by transition metal-free iminations of sulfoxides

C. A. Dannenberg, L. Fritze, F. Krauskopf and C. Bolm, Org. Biomol. Chem., 2017, 15, 1086 DOI: 10.1039/C6OB02691E

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Organic & Biomolecular Chemistry

Access to N-cyanosulfoximines by transition metal-free iminations of sulfoxides†

Abstract

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Access to N-cyanosulfoximines by transition metal-free iminations of sulfoxides

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