Preparation of 1,2-bis(pyrazol-1-yl)benzene: “Modern” Cross-Coupling vs. the “Classic” Nucleophilic Substitution Approach

Title: Preparation of 1,2-bis(pyrazol-1-yl)benzene: “Modern” Cross-Coupling vs. the “Classic” Nucleophilic Substitution Approach

Volume: 6 Issue: 1

Author(s): Olga Ivashchuk and Vladimir I. Sorokin

Affiliation:

Keywords: 1,2-bis(pyrazol-1-yl)benzene, pyrazole, 1,2-dihalobenzenes, C-N cross-coupling, fluorine nucleophilic substitution

Abstract: Several potential methods for the preparation of 1,2-bis(pyrazol-1-yl)benzene, a prospective ligand for transitional metals, starting from 1,2-dihalobenzenes and pyrazole have been studied. Cross-couplings of 1,2-dichloro-, - dibromo- and -diiodobenzenes with pyrazole using palladium and copper catalysts were unsatisfactory because of dehalogenation side reactions or a lack of reactivity. On the other hand, nucleophilic aromatic substitution of fluorine in 1,2- difluorobenzene under the action of sodium pyrazolide gave a good yield of the desired product.

Cite this article as:

Ivashchuk Olga and Sorokin I. Vladimir, Preparation of 1,2-bis(pyrazol-1-yl)benzene: “Modern” Cross-Coupling vs. the “Classic” Nucleophilic Substitution Approach, Letters in Organic Chemistry 2009; 6 (1) . https://dx.doi.org/10.2174/157017809787003232