Tandem hydroformylation/aldol condensation reactions: Synthesis of unsaturated ketones from olefins

L. Kollár, Péter Pongrácz

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Platinum-catalysed tandem hydroformylation/aldol condensation reaction of vinyl aromatics and ketones toward the corresponding α,β-unsaturated ketones were performed under syngas atmosphere in the presence of acid co-catalysts. The in situ generated catalysts modified with various ligands proved to be efficient under applied conditions. The presence of acids promotes side reactions like hydrogenation of the alkene substrate and that of the aldehyde to the corresponding alkane and alcohol, respectively. Interestingly, the hydrogenation of the condensed products is not preferred, only trace amounts of saturated products can be detected by GC-MS. In general, moderate yields can be achieved with several ketones using styrene and α-methylstyrene as substrate in hydroformylation reaction. Linear aldehydes proved to be more active in aldol condensation step, furthermore, aromatic and cyclic ketones are also feasible coupling partners to generate the corresponding unsaturated ketones. Contrary to the preceding literature, ketones possessing α-methylene group(s) showed exclusive preference for methylene functionalization in the aldol condensation reaction.

Original languageEnglish
Pages (from-to)184-188
Number of pages5
JournalJournal of Organometallic Chemistry
Volume866
DOIs
Publication statusPublished - Jul 1 2018

Fingerprint

Hydroformylation
Condensation reactions
Alkenes
Ketones
ketones
alkenes
Olefins
condensation
synthesis
Hydrogenation
Aldehydes
aldehydes
methylene
hydrogenation
catalysts
acids
Catalysts
Alkanes
Acids
Styrene

Keywords

  • Aldol condensation
  • Hydroformylation
  • Platinum
  • Tandem reaction
  • Unsaturated ketone

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Tandem hydroformylation/aldol condensation reactions : Synthesis of unsaturated ketones from olefins. / Kollár, L.; Pongrácz, Péter.

In: Journal of Organometallic Chemistry, Vol. 866, 01.07.2018, p. 184-188.

Research output: Contribution to journalArticle

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