Pd-PEPPSI catalysts bearing N-heterocyclic carbene ligands derived from caffeine and theophylline for Mizoroki–Heck and C(sp2)–H arylation reactions

Mazars, François; Etse, Koffi Senam; Zaragoza, Guillermo; Delaude, Lionel

doi:10.1016/j.jorganchem.2023.122928

Article (Scientific journals)

Pd-PEPPSI catalysts bearing N-heterocyclic carbene ligands derived from caffeine and theophylline for Mizoroki–Heck and C(sp2)–H arylation reactions

Mazars, François; Etse, Koffi Senam; Zaragoza, Guillermo et al.

2023 • In Journal of Organometallic Chemistry, 1003, p. 122928

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/309258

DOI
10.1016/j.jorganchem.2023.122928

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Keywords :

Alkaloids; Carbene ligands; Cross-coupling; Green chemistry; Hirshfeld surface; Aryl bromides; Arylation reactions; Catalyst precursors; Cross-couplings; Electron-withdrawing substituents; Green-chemistry; Hirshfeld surfaces; N-heterocyclic carbene ligands; ]+ catalyst; Biochemistry; Physical and Theoretical Chemistry; Organic Chemistry; Inorganic Chemistry; Materials Chemistry

Abstract :

[en] The activity of three Pd-PEPPSI catalyst precursors bearing N-heterocyclic carbene (NHC) ligands derived from caffeine and theophylline was tested in Mizoroki–Heck reactions between styrene and five different aryl bromides bearing electron-donating or withdrawing substituents. Moderate to excellent conversions (44–98%) were achieved within 3 h at 100 °C with K2CO3 as the base and 1 mol% of catalyst in a green water/isopropanol mixture under a normal atmosphere. Electron-withdrawing groups favored the reaction and led to the highest yields of stilbene products (up to 85% after chromatographic purification). The activity of the three [PdX2(NHC)(Py)] complexes (X = Cl, I) was also probed in the C(sp2)–H arylation of two heterocyclic substrates using the same set of five representative aryl bromides. Experimental conditions were further optimized on a model reaction (1 mol% of catalyst in DMA at 120 °C for 4 h with KOAc as the base). Gratifyingly, 1-methyl-2-pyrrolecarboxaldehyde afforded high conversions (59–99%) and yields of isolated products (49–85%), with the best results obtained again under the influence of electron-withdrawing substituents. When a more challenging substrate, viz., 3,5-dimethylisoxazole was used, modest to satisfactory conversions (41–80 %) and yields (30–69%) could still be reached with the best catalyst for each reaction. The structural properties of the complexes under investigation were compared using X-ray crystallography and Hirshfeld surface analysis.

Disciplines :

Chemistry

Author, co-author :

Mazars, François ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène

Etse, Koffi Senam ; Université de Liège - ULiège > Unités de recherche interfacultaires > Centre Interdisciplinaire de Recherche sur le Médicament (CIRM)

Zaragoza, Guillermo; Unidade de Difracción de Raios X, RIAIDT, Universidade de Santiago de Compostela, Santiago de Compostela, Spain

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène

Language :

English

Title :

Pd-PEPPSI catalysts bearing N-heterocyclic carbene ligands derived from caffeine and theophylline for Mizoroki–Heck and C(sp2)–H arylation reactions

Publication date :

15 December 2023

Journal title :

Journal of Organometallic Chemistry

ISSN :

0022-328X

Publisher :

Elsevier B.V.

Volume :

1003

Pages :

122928

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://api.elsevier.com/content/article/PII:S0022328X23003169?httpAccept=text/xml

Funding text :

The authors would like to thank Mr. François Gérardy for his technical assistance with the Mizoroki–Heck reactions and RIADT-USC for the use of its analytical facilities.

Available on ORBi :

since 28 November 2023

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