Issue 4, 2022, Issue in Progress
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RSC Advances

Synthesis of unprotected glyco-alkynones via molybdenum-catalyzed carbonylative Sonogashira cross-coupling reaction†

Mariana P. Darbem,a   Henrique A. Esteves,b   Robert A. Burrow, ORCID logo c   Antônio A. Soares-Paulino,a   Daniel C. Pimentad  and  Hélio A. Stefani ORCID logo *a  

* Corresponding authors

a Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, Avenida Prof. Lineu Prestes, 580 – Bl. 13, São Paulo, Brazil
E-mail: hstefani@usp.br

b Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge, UK

c Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil

d Instituto Butantan, São Paulo, Brazil

Abstract

Herein we report a novel Mo-catalyzed carbonylative Sonogashira cross-coupling between 2-iodoglycals and terminal alkynes. The reaction displays major improvements compared to a related Pd-catalyzed procedure previously published by our group, such as utilizing unprotected sugar derivatives as starting materials and tolerance to substrates bearing chelating groups. In this work we also demonstrate the utility of the glyco-alkynone products as platform for further functionalization by synthesizing glyco-flavones via Au-catalyzed 6-endo-dig cyclization.

Graphical abstract: Synthesis of unprotected glyco-alkynones via molybdenum-catalyzed carbonylative Sonogashira cross-coupling reaction

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Article information

DOI
https://doi.org/10.1039/D1RA08388K
Article type
Paper
Submitted
15 Nov 2021
Accepted
10 Dec 2021
First published
13 Jan 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 2145-2149

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Synthesis of unprotected glyco-alkynones via molybdenum-catalyzed carbonylative Sonogashira cross-coupling reaction

M. P. Darbem, H. A. Esteves, R. A. Burrow, A. A. Soares-Paulino, D. C. Pimenta and H. A. Stefani, RSC Adv., 2022, 12, 2145 DOI: 10.1039/D1RA08388K

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