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

Revannath L. Sutar; Nikita Erochok; Stefan M. Huber

doi:10.1039/d0ob02503h

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

Revannath L. Sutar, Nikita Erochok, Stefan M. Huber

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

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, asyn-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BAr^F₄salts, PF₆or 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.

Original language	English
Pages (from-to)	770-774
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	4
DOIs	https://doi.org/10.1039/d0ob02503h
State	Published - 28 Jan 2021
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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, asyn-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BArF4salts, PF6or 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.",

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AU - Sutar, Revannath L.

AU - Erochok, Nikita

AU - Huber, Stefan M.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/1/28

Y1 - 2021/1/28

N2 - 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, asyn-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BArF4salts, PF6or 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.

AB - 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, asyn-preorganized bidentate XB donor provided a strong performance even with 0.5 mol% loading. In contrast to the very active BArF4salts, PF6or 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.

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JO - Organic and Biomolecular Chemistry

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IS - 4

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

Abstract

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