Formic acid; Internal aromatic alkynes; Palladium catalyst; Selective reduction; Transfer hydrogenation
Inorganic Chemistry | Organic Chemistry | Physical Sciences and Mathematics
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
Chayya, Suzanne; Hijazi, Akram; Daou, Anis; Alaaeddine, Ali; Sakr, Mohamad; Younes, Ghassan; and El-Dakdouki, Mohammad
"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:
1, Article 8.
Available at: https://digitalcommons.bau.edu.lb/stjournal/vol4/iss1/8