Tandem catalytic triple-bond cleavage of alkyne in association with aldehyde, alkene, and water

Kyung Mi Cha, Eun Ae Jo, Chul Ho Jun

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

In this tandem reaction the carbon-carbon triple bond of an alkyne is catalytically cleaved in association with aldehyde, al-kene, and H2O under catalyst mixtures of Rh(I), 2-amino-3-picoline, primary amine, and acid. The reaction starts with chelation-assisted hydroacylation of the alkyne with an aldehyde. The retro-Mannich-type fragmentation of the resulting ,α,β-unsaturated ketimine by an amine and acid affords a ketimine and an aldimine, which is trapped by an alkene and give ketones after hydrolysis.

Original languageEnglish
Pages (from-to)2939-2942
Number of pages4
JournalSynlett
Issue number18
DOIs
Publication statusPublished - 2009 Dec 21

Fingerprint

Alkynes
Alkenes
Aldehydes
Amines
Picolines
Carbon
Association reactions
Acids
Water
Chelation
Ketones
Hydrolysis
Catalysts
ketimine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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Tandem catalytic triple-bond cleavage of alkyne in association with aldehyde, alkene, and water. / Cha, Kyung Mi; Jo, Eun Ae; Jun, Chul Ho.

In: Synlett, No. 18, 21.12.2009, p. 2939-2942.

Research output: Contribution to journalArticle

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