Highlights on the General Preference for Multi-Over Mono-Coupling in the Suzuki–Miyaura Reaction-Reference-Cited by-同舟云学术

Highlights on the General Preference for Multi-Over Mono-Coupling in the Suzuki–Miyaura Reaction

Published:2023-05-24 Issue:6 Volume:13 Page:928
ISSN:2073-4344
Container-title:Catalysts
language:en
Short-container-title:Catalysts

Author:

Lima Carlos F. R. A. C.¹^ORCID,Lima Marco A. L.²^ORCID,Pinto J. Ricardo M.³^ORCID,Ribeiro M. Gabriela T. C.³,Silva Artur M. S.⁴^ORCID,Santos Luís M. N. B. F.¹^ORCID

Affiliation:

1. CIQUP, Institute of Molecular Sciences (IMS)—Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, 4169-007 Porto, Portugal

2. Institut für Anorganische Chemie I, Universität Ulm Albert-Einstein-Allee 11, 89081 Ulm, Germany

3. LAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua Campo Alegre s/n, 4169-007 Porto, Portugal

4. LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal

Abstract

A systematic synthetic study was performed to explain the usual trend in selectivity towards multi-coupling, over mono-coupling, in Suzuki–Miyaura reactions. This preference was observed under different reaction conditions: for various halobenzenes, using substituents on the boronic acid, and changing the catalyst and temperature. Moreover, this reaction selectivity was found to increase for more reactive systems towards oxidative addition and more diluted media. The results constitute experimental evidence that the formation of the totally substituted coupling product is kinetically favoured by a reaction path location—the proximity between the regenerated catalyst and the newly formed coupling intermediate promotes the subsequent reaction.

Funder

Fundação para a Ciência e Tecnologia

Publisher

MDPI AG

Subject

Physical and Theoretical Chemistry,Catalysis,General Environmental Science

Link

https://www.mdpi.com/2073-4344/13/6/928/pdf

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