Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles

The Journal of Organic Chemistry
Dániel LasányiGergely L Tolnai

Abstract

For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.

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Citations

Aug 5, 2020·Chemical Communications : Chem Comm·Isabel-Maria Ramirez Y MedinaAnne Staubitz
Jan 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yuki KitamuraShuji Yasuike
Mar 1, 2019·Israel Journal of Chemistry·Zhengqing ZhaoMingming Zhang
Aug 6, 2021·Journal of Natural Products·Emma K DavisonMargaret A Brimble
Jun 14, 2019·The Journal of Organic Chemistry·Joseph S CapaniJianglin Colin Liang

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