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

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 start...

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Published in:RSC advances 2022-01, Vol.12 (4), p.2145-2149
Main Authors: Darbem, Mariana P, Esteves, Henrique A, Burrow, Robert A, Soares-Paulino, Antônio A, Pimenta, Daniel C, Stefani, Hélio A
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Summary: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. Thermal ellipsoid representation of compound 3a .
ISSN:2046-2069
DOI:10.1039/d1ra08388k