Roles of reactants for Suzuki C-C cross-coupling reaction using molecular volcano plot

Name: Kwanchanok Kaewkwan

Organization : Chulalongkorn University. Faculty of Science

Name: Vudhichai Parasuk

Organization : Chulalongkorn University. Faculty of Science

Name: Boodsarin Sawatlon

Organization : Chulalongkorn University. Faculty of Science

Email : Boodsarin.s@chula.ac.th

keyword: Suzuki coupling reaction

LCSH: Palladium catalysts

; Carbon-carbon bond formation

; Cross-coupling reaction

; Catalyst activity

Abstract: Suzuki-Miyaura C-C cross-coupling reaction is a powerful and well-known reaction to construct C-C bond due to its easily accessibility of organoboron reactants and its non-harmful condition reaction. However, this reaction does not always exhibit excellent efficiency especially when changing reactants, and the reasons behind its behavior are still unclear. To understand a more complete picture of the Suzuki C-C cross-coupling reaction, we have investigated the effects of both electrophile (R1-Br) and nucleophile (R2-B(OH)2) reactants when catalyzed by Pd(PMe3)2 using Density Functional Theory (DFT) calculations and molecular volcano plots. Among five selected different substituents on R1 and R2 (furan, pyridine, phenyl, styrene and vinyl), we found that the reactions involving 2-bromofuran, when paired with any of boronic acid proceed the lowest energy barrier in the rate-determining step compared to others. Molecular volcano plots also illustrate that the feasible reaction with 2-bromofuran reactant is resulted from the balance of interaction between reactants and Pd(PMe3)2 catalyst, leading to the effortless oxidative addition and reductive elimination processes. The order of the interaction between each reactant and catalyst, ranking from strongest to weakest, is furan, pyridine, styrene, phenyl and vinyl, where furan is locating at the most balanced point (volcano top) of interaction

King Mongkut's University of Technology North Bangkok. Central Library

Address: BANGKOK

Email: library@kmutnb.ac.th

Created: 2024

Modified: 2024-12-11

Issued: 2024-12-11

บทความ/Article

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BibliograpyCitation : In Kasetsart University. Faculty of Science. The Pure and Applied Chemistry International Conference 2024 (PACCON 2024) (pp.1092-1097). Bangkok : Kasetsart University, 2024

eng

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