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Mukaiyama Aldol Reaction Catalyzed by (Benz)imidazolium-Based Halogen Bond Donors

preprint
submitted on 18.08.2020 and posted on 19.08.2020 by Revannath L. Sutar, Nikita Erochok, Stefan Huber
A series of cationic monodentate and bidentate iodo(benz)­imidazolium-based halogen bond (XB) donors were employed as catalysts in a Mukaiyama aldol reaction. While 5 mol% of a monodentate variant showed noticeable activity, a syn-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BArF4 salts, PF6 or OTf salts were either inactive or showed background reaction. Repetition experiments clearly ruled out a potential hidden catalysis by elemental iodine and demonstrated the stability of our catalyst over three consecutive cycles.

Funding

ERC Starting Grant 638337

Dozentenstipendium (Fonds der Chemischen Industrie)

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

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