Boron trichloride mediated alkyne-aldehyde coupling reactions

Min Liang Yao, Michael P. Quinn, George Kabalka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The boron trichloride mediated reaction of aryl aldehydes and alkynes can be used to selectively generate either (Z,Z)- or (Z,E)-1,5-dichloro-1,4-dienes as major products, depending on the reaction conditions employed. To investigate the mechanism of this important carbon-carbon bond forming reaction, the boron trichloride mediated reaction of phenylacetylene with p-bromobenzaldehyde was chosen as the model system. Interestingly, when the coupling reactions are carried out below -60°C, (E,E)-1,5-dichloro-1,4-dienes are also formed. The ratios of (Z,Z)-, (Z,E)-, and (E,E)-1,5-dichloro-1,4-dienes were correlated to the reaction conditions using gas chromatography-mass spectrometry. The results of the investigation can be used to explain why the ratio of (Z,E)-, (Z,Z)-, and (E,E)-1,5-dichloro-1,4-pentadiene products change very dramatically when changes are made in either the sequence of addition of the reagents or the reaction temperature.

Original languageEnglish (US)
Pages (from-to)779-785
Number of pages7
JournalHeterocycles
Volume80
Issue number2
DOIs
StatePublished - Mar 1 2010
Externally publishedYes

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Alkynes
Aldehydes
Carbon
Alkadienes
Gas chromatography
Gas Chromatography-Mass Spectrometry
Mass spectrometry
Temperature
boron trichloride
phenylacetylene

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Boron trichloride mediated alkyne-aldehyde coupling reactions. / Yao, Min Liang; Quinn, Michael P.; Kabalka, George.

In: Heterocycles, Vol. 80, No. 2, 01.03.2010, p. 779-785.

Research output: Contribution to journalArticle

Yao, Min Liang ; Quinn, Michael P. ; Kabalka, George. / Boron trichloride mediated alkyne-aldehyde coupling reactions. In: Heterocycles. 2010 ; Vol. 80, No. 2. pp. 779-785.
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