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Synthesis 2018; 50(17): 3307-3321
DOI: 10.1055/s-0037-1610197
DOI: 10.1055/s-0037-1610197
feature
One-Pot Conversion of Aldehydes and Ketones into 1-Substituted and 1,4-Disubstituted 1,3-Enynes
Weitere Informationen
Publikationsverlauf
Received: 01. Juni 2018
Accepted after revision: 05. Juni 2018
Publikationsdatum:
23. Juli 2018 (online)
This article is dedicated to Professor Cam Oehlschlager, senior supervisor and friend
Abstract
Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generates the operational equivalent of 1,3-dilithiopropyne, which upon treatment with aldehydes or ketones, produces the corresponding alkoxy lithium acetylide intermediates. Reaction of this alkoxide with tosyl chloride, and t-BuLi produces 1-substituted, or 1,1-disubstituted 1,3-enynes in a one-pot reaction. When this lithium acetylide intermediates, obtained by this procedure, were used to perform palladium-catalyzed cross-coupling reactions, followed by addition of thionyl chloride and pyridine, 1,4-disubstituted or 1,1,4-trisubstituted 1,3-enynes were obtained in a one-pot protocol.
Key words
1,3-dilithiopropyne - lithium acetylides - 1,3-enynes - palladium catalysis - cross-coupling - propargylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610197. Copies of 1H NMR and 13C NMR spectra of all compounds prepared and shown in Tables 3 and 5 are provided.
- Supporting Information
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