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

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

Research output: Contribution to journalArticlepeer-review

4 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 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.

Original languageEnglish
Pages (from-to)770-774
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number4
DOIs
StatePublished - 28 Jan 2021
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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