Issue 17, 2019
From the journal:

RSC Advances

Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction†

Mariana P. Darbem,a   C. Henrique A. Esteves,a   Isadora M. de Oliveira,b   Joel S. Reis,a   Daniel C. Pimentac  and  Hélio A. Stefani ORCID logo *a  

* Corresponding authors

a Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil
E-mail: hstefani@usp.br
Tel: +55 11 3091-3654

b Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

c Instituto Butantã, São Paulo, SP, Brazil

Abstract

A carbonylative Sonogashira coupling approach to the synthesis of glyco-alkynones is described. Eighteen examples were obtained in moderate do nearly quantitative yields under mild conditions employing Mo(CO)6 as a safe carbon monoxide source. Functionalization of the alkynyl moiety via cycloaddition with organic azides provided six examples of glyco-triazoles.

Graphical abstract: Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction

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Article information

DOI
https://doi.org/10.1039/C9RA00523D
Article type
Paper
Submitted
21 Jan 2019
Accepted
14 Mar 2019
First published
25 Mar 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 9468-9474

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Synthesis of D-glyco-alkynone derivatives via carbonylative Sonogashira reaction

M. P. Darbem, C. H. A. Esteves, I. M. de Oliveira, J. S. Reis, D. C. Pimenta and H. A. Stefani, RSC Adv., 2019, 9, 9468 DOI: 10.1039/C9RA00523D

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