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Solvent-controlled hydrogenation of 2’-hydroxychalcones: a simple solution to the total synthesis of Bussealins

Autor(es) y otros:
Soto García, MartínAutoridad Uniovi; González Soengas, RaquelAutoridad Uniovi; Rodríguez Solla, HumbertoAutoridad Uniovi
Palabra(s) clave:

Bussealins

Chalcones

Green solvents

Hydrogenation

Palladium

Fecha de publicación:
2020
Citación:
Advanced Synthesis and Catalysis, 362, p. 5422–5431 (2020); doi:10.1002/adsc.202000892
Descripción física:
5422-5431
Resumen:

A solvent-controlled hydrogenation of 2’-hydroxychalcones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of 2’-hydroxychalcones using EtOH as solvent provided the corresponding 1,3-diarylpropanes in excellent yields. On the contrary, when the hydrogenation was performed in DCM, the corresponding dihydrochalcones were isolated. Switching the reaction solvent to n-BuOH/H2O (1:1), afforded 1,3-diarylpropanols from moderate to good yields. The methodology here reported offers a straightforward, simple and cost-effective method for the preparation of a wide variety of 2’- hydroxy-1,3-diarylpropanes derivatives, and was also applied to the preparation of natural Bussealins C and D

A solvent-controlled hydrogenation of 2’-hydroxychalcones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of 2’-hydroxychalcones using EtOH as solvent provided the corresponding 1,3-diarylpropanes in excellent yields. On the contrary, when the hydrogenation was performed in DCM, the corresponding dihydrochalcones were isolated. Switching the reaction solvent to n-BuOH/H2O (1:1), afforded 1,3-diarylpropanols from moderate to good yields. The methodology here reported offers a straightforward, simple and cost-effective method for the preparation of a wide variety of 2’- hydroxy-1,3-diarylpropanes derivatives, and was also applied to the preparation of natural Bussealins C and D

URI:
http://hdl.handle.net/10651/57746
ISSN:
1615-4169
DOI:
10.1002/adsc.202000892
Patrocinado por:

This work has received financial support from the Ministerio de Ciencia e Innovación (PID2019-109253RBI00) and Principado de Asturias (FICYTIDI/2018/000181). Partial financial support by Arcelor Mittal (R&D-Principado de Asturias; FUO-286-18) is gratefully acknowledged. M.S. thanks the University of Oviedo for a predoctoral contract.

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