Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction is a significant reaction for obtaining industrially important products. The current research work deals with intensification of reaction of 4-bromoanisole and phenylboronic acid catalyzed with 5wt% Pd/C (5% by weight Pd supported on C available as commercial catalyst) using ultrasound and more importantly, without use of any additional phase transfer catalyst. Heterogeneous catalyst has been selected in the present work so as to harness the benefits of easy separation and the possible limitations of heterogeneous operation are minimized by introducing ultrasonic irradiations. The effect of operating parameters such as ultrasound power, temperature, catalyst loading and molar ratio on the progress of reaction has been investigated. It has been observed that an optimum power, temperature and catalyst loading exist for maximum benefits whereas higher molar ratio was found to be favourable for the progress of the reaction. Also, the use of ultrasound reduced the reaction time from 70min required in conventional approach to only 35min under conditions of frequency of 22kHz, power dissipation of 40W and catalyst loading as 1.5mol% (refers to total quantum of catalyst used in the work) in ethanol-water system under ambient conditions. The work also demonstrated successful results at ten times higher volume as compared to the normally used volumes in the case of simple ultrasonic horn. Overall, the work has successfully demonstrated process intensification benefits obtained due to the use of ultrasound for heterogeneously catalyzed Suzuki-Miyaura cross-coupling reaction.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.ultsonch.2017.01.037DOI Listing

Publication Analysis

Top Keywords

suzuki-miyaura cross-coupling
12
cross-coupling reaction
12
catalyst loading
12
heterogeneously catalyzed
8
catalyzed suzuki-miyaura
8
reaction
8
reaction ultrasound
8
operating parameters
8
power temperature
8
temperature catalyst
8

Similar Publications

Mapping the molecular mechanism of zinc catalyzed Suzuki-Miyaura coupling reaction: a computational study.

Org Biomol Chem

January 2025

Department of Chemistry, CMS College Kottayam (Autonomous), Kottayam, Kerala, 686001, India.

The Suzuki-Miyaura Coupling (SMC) reaction is a powerful method for forming carbon-carbon bonds in organic synthesis. Recent advancements in SMC reactions have introduced first-row transition metal catalysts, with zinc garnering significant interest due to its cost-effective and eco-friendly nature. Despite progress in experimental protocols, the mechanistic details of zinc-catalyzed SMC reactions are limited.

View Article and Find Full Text PDF

Although numerous transition-metal catalyzed cross-coupling reactions of alkenyl electrophiles with a sulfur(VI) leaving group, mainly alkenyl sulfones, have been developed, most rely heavily on highly nucleophilic Grignard reagents, and the use of organoboron reagents remains challenging. We report herein facile preparation and the following Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of alkenyl sulfoximine, a monoaza analog of sulfone. The condensation of alkyl sulfoximine with aldehydes, developed in this study, makes alkenyl sulfoximines more readily available.

View Article and Find Full Text PDF

Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45-90%). This cascade involves an initial Suzuki-Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C-H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[]fluoranthenes, which are all structurally relevant to benzo[]fluoranthene-based fungal natural products.

View Article and Find Full Text PDF
Article Synopsis
  • A new palladium-catalyzed method has been developed to synthesize three natural products: (-)-lyngbyatoxin, (-)-teleocidin A2, and (-)-7-geranylindolactam V, using a technique called the Suzuki-Miyaura reaction.
  • This approach utilizes a ligand-controlled cross-coupling strategy, making it possible to create these compounds from a single advanced synthetic intermediate, which is the most efficient method reported to date.
  • Following the synthesis, research was conducted on cancer cell lines to investigate the potential cancer-fighting properties of these natural products.
View Article and Find Full Text PDF

Optically active cofacial ABCD-Pt(II)-porphyrin dimer exhibits bright circularly polarized phosphorescence.

Chem Commun (Camb)

January 2025

Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University 1 Gakuen Uegahara, Sanda, Hyogo 669-1330, Japan.

Article Synopsis
  • The synthesis of a chiral cofacial ABCD-Pt(II)-porphyrin dimer was successfully completed using a Pt-templated method followed by a Suzuki-Miyaura cross-coupling process.
  • The resulting enantiomers showcased bright red circularly polarized phosphorescence.
  • The phosphorescence had a high value of over 10 M cm, indicating strong optical properties.
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!