Imidazolidine Hydride Donors in Palladium-Catalyzed Alkyne Hydroarylation

Soe L Tun; S V Santhana Mariappan; F Christopher Pigge

doi:10.1021/acs.joc.2c00725

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Imidazolidine Hydride Donors in Palladium-Catalyzed Alkyne Hydroarylation

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Imidazolidine Hydride Donors in Palladium-Catalyzed Alkyne Hydroarylation

Soe L Tun, S V Santhana Mariappan and F Christopher Pigge

Journal of organic chemistry, Vol.87(12), pp.8059-8070

06/01/2022

DOI: 10.1021/acs.joc.2c00725

PMCID: PMC9490851

PMID: 35649131

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Abstract

Aldehyde-derived imidazolidines participate as hydride donors in intramolecular reductive Heck-type reactions. N,N′-Diphenylimidazolidines prepared from ortho-alkynyl benzaldehydes underwent regio- and stereoselective palladium-catalyzed hydroarylation followed by formal 1,5-hydride transfer and reductive elimination to afford substituted alkenes and imidazolium moieties, the latter conveniently converted in situ to ring-opened benzanilides to simplify product isolation. Internal alkynes were converted to trisubstituted alkenes via a syn hydroarylation process, while a terminal alkyne was converted to a cis alkene via a formal trans hydroarylation reaction. Benzanilide products could be converted to carboxylic acid derivatives under basic conditions, resulting in the net conversion of alkynyl aldehydes to alkenyl carboxylic acids. A styrene derivative with an attached N,N′-dimethylbenzimidazoline hydride donor was also found to undergo an analogous hydroarylation/benzimidazoline oxidation to give a diarylethane product.

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Details

Title: Subtitle: Imidazolidine Hydride Donors in Palladium-Catalyzed Alkyne Hydroarylation
Creators: Soe L Tun - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
S V Santhana Mariappan - Central NMR Facility, University of Iowa, Iowa City, Iowa 52242, United States
F Christopher Pigge - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Resource Type: Journal article
Publication Details: Journal of organic chemistry, Vol.87(12), pp.8059-8070
DOI: 10.1021/acs.joc.2c00725
PMID: 35649131
PMCID: PMC9490851
NLM abbreviation: J Org Chem
ISSN: 0022-3263
eISSN: 1520-6904
Publisher: American Chemical Society
Grant note: name: Department of Chemistry, University of Iowa; DOI: 10.13039/100012011, name: Graduate College, University of Iowa
Language: English
Date published: 06/01/2022
Academic Unit: Radiology; Chemistry
Record Identifier: 9984267360302771

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