Palladium-catalyzed allylation of 2- and 4-alkylpyridines via N-allyl alkylidene dihydropyridine intermediates.

Allylation Catalysis Dihydropyridine Palladium Pyridine

Journal

Tetrahedron letters
ISSN: 0040-4039
Titre abrégé: Tetrahedron Lett
Pays: England
ID NLM: 2984819R

Informations de publication

Date de publication:
19 Sep 2023
Historique:
pmc-release: 19 09 2024
medline: 16 10 2023
pubmed: 16 10 2023
entrez: 16 10 2023
Statut: ppublish

Résumé

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 (KO

Identifiants

pubmed: 37841749
doi: 10.1016/j.tetlet.2023.154701
pmc: PMC10569290
mid: NIHMS1926973
pii:
doi:

Types de publication

Journal Article

Langues

eng

Subventions

Organisme : NIGMS NIH HHS
ID : T32 GM008365
Pays : United States

Déclaration de conflit d'intérêts

Declaration of Competing Interests The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Références

J Am Chem Soc. 2007 Apr 11;129(14):4138-9
pubmed: 17371027
J Org Chem. 2023 Mar 17;88(6):3998-4002
pubmed: 36848377
J Am Chem Soc. 2009 Sep 2;131(34):12056-7
pubmed: 19645450
J Org Chem. 2023 Jun 16;88(12):7821-7829
pubmed: 36562778
Org Lett. 2021 Feb 19;23(4):1463-1467
pubmed: 33544606
J Med Chem. 2014 Dec 26;57(24):10257-74
pubmed: 25255204
Angew Chem Int Ed Engl. 2022 May 23;61(22):e202200602
pubmed: 35243738
J Am Chem Soc. 2008 Oct 29;130(43):14092-3
pubmed: 18826305
J Org Chem. 2016 Nov 4;81(21):10266-10278
pubmed: 27379459
J Am Chem Soc. 2013 Nov 20;135(46):17602-9
pubmed: 24147620
Chem Sci. 2020 Dec 10;12(4):1503-1512
pubmed: 34163914
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9465-9469
pubmed: 29863762
J Med Chem. 2014 Jul 24;57(14):5845-59
pubmed: 24471928
Angew Chem Int Ed Engl. 2016 Jan 18;55(3):1070-4
pubmed: 26756444
Angew Chem Int Ed Engl. 2017 Mar 27;56(14):4002-4005
pubmed: 28266102
J Am Chem Soc. 2019 Aug 21;141(33):13066-13073
pubmed: 31343170

Auteurs

Grant N Shivers (GN)

Department of Chemistry, University of Iowa Iowa City, Iowa, 52242, USA.

F Christopher Pigge (FC)

Department of Chemistry, University of Iowa Iowa City, Iowa, 52242, USA.

Classifications MeSH