Regio- and stereoselective synthesis of alkenylphosphines: A rhodium-catalyzed hydrophosphination of alkynes using a silylphosphine

Journal of Organic Chemistry

Volumn 71, Issue 24, 2006, Pages 9248-9251

  Hayashi, Minoru ^a   Matsuura, Yutaka ^a   Watanabe, Yutaka ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; ELECTRONS; OLEFINS; RHODIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALKYNES; CARBOXYL GROUPS; HYDROPHOSPHINATION; SILYLPHOSPHINE;

AMINES;

ALKENYL GROUP; ALKYL GROUP; ALKYNE DERIVATIVE; CARBOXYL GROUP; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; HYDROPHOSPHINATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 33751575643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061739f     Document Type: Article

References (32)

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27. 5, 140°C/0.1 mmHg, 2 h) and was handled with ordinary care.
28. The products of hydrophosphination, alkenylphosphines, did not interfere with the active species of the catalyst, though the products have a P(III) atom to coordinate. The reaction proceeded smoothly with the same reactivity and selectivity even in the presence of the alkenylphosphine product added externally to the catalyst.
29. The color of the reaction mixture turned yellow again when all of the substrate was consumed.
30. 16 We found that substituted propiolates 2h,i did not react directly with silylphosphines, even though those alkynes are classified as electron deficient alkynes. Therefore, 2h,i could be applied as substrates of the present hydrophosphination.
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