Distinguishing between Linear and Non-Linear (Cooperative) Substrate Activation Mechanisms in the Sonogashira Reaction under “Ligand-Free” and “Copper-Free” Conditions

E. V. Larina; Ларина Е. В.; A. A. Kurokhtina; Курохтина А. А.; N. A. Lagoda; Лагода Н. А.; A. F. Schmidt; Шмидт А. Ф.

doi:10.31857/S0453881123060102

Distinguishing between Linear and Non-Linear (Cooperative) Substrate Activation Mechanisms in the Sonogashira Reaction under “Ligand-Free” and “Copper-Free” Conditions

Authors: Larina E.V.¹, Kurokhtina A.A.¹, Lagoda N.A.¹, Schmidt A.F.¹
Affiliations:
1. Irkutsk State University, Chemical Department
Issue: Vol 64, No 6 (2023)
Pages: 737-748
Section: ARTICLES
URL: https://rjonco.com/0453-8811/article/view/660310
DOI: https://doi.org/10.31857/S0453881123060102
EDN: https://elibrary.ru/KUKDLB
ID: 660310

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Abstract
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Abstract

The results are presented on the comparative studies of the differential selectivity patterns in the Sonogashira reaction with a pair of competing aryl acetylenes in the “ligand-free” and “copper-free” conditions when varying the nature and concentration of aryl halides and base. The revealed sensitivity of the differential selectivity of competing aryl acetylenes to aryl halide nature unambiguously indicated that the substrates were activated through linear mechanism from kinetic view. An absence of any influence of the nature and concentration of the base on the differential selectivity of competing aryl acetylenes indicated the irreversible character of the step of their activation.

Keywords

Sonogashira reaction, Cu- and ligand-free conditions, palladium, mechanism, kinetics, differential selectivity

References

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