ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

A Bidentate iodine(III)-Based Halogen Bond Donor as Powerful Organocatalyst

preprint
submitted on 29.09.2020, 10:14 and posted on 30.09.2020, 06:25 by Flemming Heinen, Dominik Reinhard, Elric Engelage, Stefan Huber
In contrast to iodine(I)-based halogen bond donors,
iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels-Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly
surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural analysis and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF3.

Funding

Deutsche Forschungsgemeinschaft (RESOLV, EXC 2033 - 390677874)

Fonds der Chemischen Industrie (Dozentenstipendium)

History

Email Address of Submitting Author

stefan.m.huber@rub.de

Institution

Ruhr-University Bochum

Country

Germany

ORCID For Submitting Author

0000-0002-4125-159X

Declaration of Conflict of Interest

No conflict of interest.

Exports

Read the published paper

in Angewandte Chemie International Edition

ChemRxiv

Exports