PALLADIUM (II)-CATALYZED SELECTIVE REDUCTION OF 4’-(PHENYLETHYNL)ACETOPHENONE IN THE PRESENCE OF A FORMIC ACID-TRIETHYLAMINE MIXTURE

Authors

Suzanne Chayya, Department of Chemistry, Faculty of Science, Beirut Arab UniversityFollow
Akram Hijazi, Doctoral School of Science and Technology, Platform for Research and Analysis in Environmental Sciences (PRASE), Lebanese UniversityFollow
Anis Daou, Pharmaceutical Sciences Department, College of Pharmacy, Qatar UniversityFollow
Ali Alaaeddine, Department of Chemistry, Faculty of Science, Lebanese UniversityFollow
Mohamad Sakr, Doctoral School of Science and Technology, Platform for Research and Analysis in Environmental Sciences (PRASE),Lebanese UniversityFollow
Ghassan Younes, Department of Chemistry, Faculty of Science, Beirut Arab UniversityFollow
Mohammad El-Dakdouki, Department of Chemistry, Faculty of Science, Beirut Arab UniversityFollow

Keywords

Formic acid; Internal aromatic alkynes; Palladium catalyst; Selective reduction; Transfer hydrogenation

Disciplines

Inorganic Chemistry | Organic Chemistry | Physical Sciences and Mathematics

Abstract

An efficient and straightforward palladium acetylacetonate-catalyzed hydrogen transfer of 4'- (phenylethynyl)acetophenone was developed in this study. Formic Acid was found to be the best hydrogen source in this catalytic system in the presence of triethylamine. Excellent conversions and selectivity were obtained in reducing the starting internal aromatic alkyne to either (E)-1-(4- styrylphenyl)ethanone or an interesting cyclic product, 1-(phenanthrene-3-yl)ethenone, over the ketone functional group present. Over-reduction was rarely seen. The reaction conditions were optimized in terms of the choice of the palladium catalyst, temperature, solvent, and the H-donor/base combination. Using this catalytic system, a one-step synthetic pathway of the hindered cyclic ketone was afforded in excellent yields.

Author ORCID Identifier

Suzanne Chayya https://orcid.org/0000-0002-2375-8135

Akram Hijazi https://orcid.org/0000-0003-4984-8531

Anis Daou https://orcid.org/0000-0001-8495-3076

Ali Alaaeddine https://orcid.org/0000-0001-5188-6655

Mohamad Sakr https://orcid.org/0000-0001-5024-1388

Ghassan Younes https://orcid.org/0000-0001-6927-3523

Mohammad El-Dakdouki https://orcid.org/0000-0003-0679-2267

Recommended Citation

Chayya, Suzanne; Hijazi, Akram; Daou, Anis; Alaaeddine, Ali; Sakr, Mohamad; Younes, Ghassan; and El-Dakdouki, Mohammad (2022) "PALLADIUM (II)-CATALYZED SELECTIVE REDUCTION OF 4’-(PHENYLETHYNL)ACETOPHENONE IN THE PRESENCE OF A FORMIC ACID-TRIETHYLAMINE MIXTURE," BAU Journal - Science and Technology: Vol. 4: Iss. 1, Article 8.
DOI: https://doi.org/10.54729/LJPH1001

ISSN

2959-331X