Journal article
Palladium-catalyzed allylation of 2- and 4-alkylpyridines via N-allyl alkylidene dihydropyridine intermediates
Tetrahedron letters, Vol.128, 154701
09/2023
DOI: 10.1016/j.tetlet.2023.154701
PMCID: PMC10569290
PMID: 37841749
Abstract
A method to introduce allyl or cinnamyl groups to the picolyl positions of 2- or 4-alkylpyridines is described. Substituted N-allyl pyridinium salts are first treated with base (KOtBu) followed by catalytic [(η3-allyl)PdCl]2 and PPh3 to result in formal Pd-catalyzed transfer of N-allyl groups to the pyridine periphery. The reaction is believed to proceed through initial formation of nucleophilic alkylidene dihydropyridine intermediates that react with (π-allyl)Pd(II) electrophiles, thereby regenerating N-allyl pyridinium cations. Catalytic turnover and liberation of pyridine products is then achieved by oxidative addition of Pd(0) to these activated allyl groups.
Details
- Title: Subtitle
- Palladium-catalyzed allylation of 2- and 4-alkylpyridines via N-allyl alkylidene dihydropyridine intermediates
- Creators
- Grant N. Shivers - University of IowaF. Christopher Pigge - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.128, 154701
- DOI
- 10.1016/j.tetlet.2023.154701
- PMID
- 37841749
- PMCID
- PMC10569290
- NLM abbreviation
- Tetrahedron Lett
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Grant note
- DOI: 10.13039/100012675, name: Center for Biocatalysis and Bioprocessing, University of Iowa; DOI: 10.13039/100000002, name: National Institutes of Health, award: T32-GM008365
- Language
- English
- Date published
- 09/2023
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984459655302771
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