Coupling reaction of 1-alkynes with alkenyl halides in the presence of (Ph3P)4Pd/CuI with PhCH2N+Et3 Cl- as phase transfer reagent gave high yields of 1,3-enynes.  E.g., coupling of H2C:CMeBr with Me(CH2)4C≡CH (I) in C6H6/10% aq. NaOH gave 80% H2C:CMeC≡C(CH2)4Me.  The reaction of alkynes with alkenyl halides of known configuration occurred stereospecifically.  E.g., reaction of (E)-BuCH:CHI with I gave 50% (E)-BuCH:CHC≡C(CH2)4Me, exclusively.  The usefulness of the reaction was shown by the prepn. of some insect sex pheromones.

Insect sex pheromones: palladium-catalyzed synthesis of aliphatic 1,3-enynes by reaction of 1-alkynes with alkenyl halides under phase transfer conditions

ROSSI, RENZO;CARPITA, ADRIANO;
1982

Abstract

Coupling reaction of 1-alkynes with alkenyl halides in the presence of (Ph3P)4Pd/CuI with PhCH2N+Et3 Cl- as phase transfer reagent gave high yields of 1,3-enynes.  E.g., coupling of H2C:CMeBr with Me(CH2)4C≡CH (I) in C6H6/10% aq. NaOH gave 80% H2C:CMeC≡C(CH2)4Me.  The reaction of alkynes with alkenyl halides of known configuration occurred stereospecifically.  E.g., reaction of (E)-BuCH:CHI with I gave 50% (E)-BuCH:CHC≡C(CH2)4Me, exclusively.  The usefulness of the reaction was shown by the prepn. of some insect sex pheromones.
Rossi, Renzo; Carpita, Adriano; QUIRICI M., G; Gaudenzi, M. L.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/5448
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? 77
social impact