HMPA-Free Synthesis of TMS-Substituted Alkynes

TMS-substituted alkynes are versatile building blocks in organic synthesis. Traditional synthesis involves alkyne deprotonation and the reaction with TMSCl. Recently, TMS-acetylene has become an increasingly inexpensive bulk chemical, offering an attractive alternative to accessing TMS-substituted a...

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Bibliographic Details
Published inOrganometallics Vol. 43; no. 9; pp. 929 - 933
Main Authors Cordier, Marie, Müller, Daniel S., Devillard, Marc
Format Journal Article
LanguageEnglish
Published American Chemical Society 13.05.2024
Subjects
Chemical Sciences
Organic chemistry
Hydrocarbons
Substitution reactions
Acetylide
Lithium
Anions
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Summary:TMS-substituted alkynes are versatile building blocks in organic synthesis. Traditional synthesis involves alkyne deprotonation and the reaction with TMSCl. Recently, TMS-acetylene has become an increasingly inexpensive bulk chemical, offering an attractive alternative to accessing TMS-substituted alkynes, especially when the alkyne is expensive or not commercially available. However, this route has been established with carcinogenic HMPA as a cosolvent. In this work, we disclose optimized conditions utilizing DMPU as a substitute for HMPA.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.4c00091