Issue 4, 2021

Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors

Abstract

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 through Lewis base catalysis. Repetition experiments clearly ruled out a potential hidden catalysis by elemental iodine and demonstrated the stability of our catalyst over three consecutive cycles.

Graphical abstract: Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors

Supplementary files

Article information

Article type
Communication
Submitted
15 12 2020
Accepted
05 1 2021
First published
11 1 2021

Org. Biomol. Chem., 2021,19, 770-774

Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors

R. L. Sutar, N. Erochok and S. M. Huber, Org. Biomol. Chem., 2021, 19, 770 DOI: 10.1039/D0OB02503H

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