Fluoride-Assisted Activation of Calcium Carbide: A Simple Method for the Ethynylation of Aldehydes and Ketones

The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide “ate”-complex that readily adds to carbonyl...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 11; pp. 2808 - 2811
Main Authors Hosseini, Abolfazl, Seidel, Daniel, Miska, Andreas, Schreiner, Peter R.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.06.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
CATALYSIS
TANDEM
ACETYLENE
ANALOGS
ACETYLIDES
RING
BOND FORMATION
PROPARGYL ALCOHOLS
DERIVATIVES
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Summary:The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide “ate”-complex that readily adds to carbonyl groups. Aliphatic aldehydes and ketones generally provide high yields, whereas aromatic carbonyls afford propargylic alcohols with moderate to good yields. The use of calcium carbide as a safe acetylide ion source along with economic amounts of TBAF·3H2O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.
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USDOE Office of Science (SC), Basic Energy Sciences (BES)
AC02-76SF00515
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01219