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

Published version
Peer-reviewed

Type

Article

Change log

Authors

Darbem, Mariana P 
Esteves, Henrique A 
Soares-Paulino, Antônio A 
Pimenta, Daniel C 

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.

Description

Keywords

3405 Organic Chemistry, 34 Chemical Sciences

Journal Title

RSC Adv

Conference Name

Journal ISSN

2046-2069
2046-2069

Volume Title

12

Publisher

Royal Society of Chemistry (RSC)