Cesium hydroxide: A superior base for the catalytic alkynylation of aldehydes and ketones and catalytic alkenylation of nitriles

Angewandte Chemie - International Edition

Volumn 38, Issue 10, 1999, Pages 1463-1465

  Tzalis, Dimitrios ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Alkynylation; C H activation; Carbonyl compounds; Cesium hydroxide; Vinylation

Indexed keywords

ALDEHYDE; CESIUM HYDROXIDE; HYDROXIDE; KETONE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; DIASTEREOISOMER; REACTION ANALYSIS; REACTION TIME; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033577829     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990517)38:10<1463::AID-ANIE1463>3.0.CO;2-H     Document Type: Article

References (23)

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15. 2O is commercially available (Aldrich) and has found applications as a catalyst in the polymerization of cyclic siloxanes.
16. Cesium carbonate is not effective in the activation of alkynes but has been used as a base for alkylations: a) S.-S. Wang, B. F. Gisin, D. P. Winter, R. Makofske, I. D. Kulesha, C. Tzougraki, J. Meierhofer, J. Org. Chem. 1977, 42, 1286;
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21. Aromatic aldehydes and ketones seem to undergo side reactions and are not suited for this catalysis.
22. The phase transfer catalyzed vinylation of phenylacetonitriles with stoichiometric amounts of NaOH has been described, see M. Makosza, Tetrahedron Lett. 1966, 5489.
23. A patent has been filed in colaboration with BASFAG (Ludwigshafen).