Work

Impact of the Olefin and Diazene Structure on the Heterofunctional Azo Metathesis Catalyzed by the First-Generation Grubbs Catalyst

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide In this work, we computationally studied the influence of the change in the substrate structure on the course of the heterofunctional cross-metathesis reaction between azo compounds and olefins catalyzed by the first-generation Grubbs catalyst. The highest reaction rates were predicted for symmetric, bulky diazenes and sterically uncrowded olefins. Other studied azo compounds have much higher energy barriers in the crucial steps in the catalyst initiation phase, while larger olefins are characterized by high energy barriers in the second part of the catalytic cycle. Our analysis suggests that Grubbs-like catalysts can be efficiently used in heterofunctional azo metathesis only for a limited number of olefin-azo compound combinations, such as 1,2-diphenyldiazene and ethylene to produce N-phenylmethanimine.

Source: Organometallics

DOI: 10.1021/acs.organomet.4c00264

Authors: Magdalena Jawiczuk, Bartosz Trzaskowski

Institution: University of Warsaw

Language: English

Topic: Synthetic Organic Chemistry Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Narodowe Centrum Nauki