Work

One-Pot Regio- and Diastereoselective Gold-Catalyzed Propargylation of in Situ Activated Chromones and Consecutive Cyclization

Year: 2024

Type: article

Abstract: Herein, we report a gold-catalyzed propargylation of chromone derivatives by propargylsilanes. Chromones are synergistically activated by the silylium cation resulting from the gold activation of the propargylsilane. The reaction exclusively occurs at the C2-position of the chromone, and a single diastereoisomer is formed. Computational studies performed on the reaction mechanism rationalize the formation of the preferred diastereoisomer. Finally, a dual consecutive cascade reaction based on different gold catalysts enables the formation of complex tricyclic compounds.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03812

Authors: Julio Álvarez-Valle, Sergio Fernández, Cecilia Merino-Robledillo, Ignacio Funes-Ardoiz, Diego Sampedro, Javier Santamaría

Institutions: Universidad de Oviedo, Universidad de La Rioja

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Agencia Estatal de Investigación