Cyclic and acyclic beta-ketoesters 4, a typical cyclic alpha-diketone 5 and a typical cyclic beta-diketone 6 were convened to the corresponding vinyl nonaflates of general formula 7, 8 and 9, respectively, by reaction with 1.2-1.5 equiv of NaH in DMF at 20-55 degrees C followed by treatment with 1.15-1.30 equiv of perfluoro-1-butanesulfonyl fluoride at 20 degrees C. These vinyl nonaflates, which were purified by MPLC on silica gel, proved to be excellent electrophiles in Pd-catalyzed cross-coupling reactions with aryl-, 1-alkynyl- and alkylzinc chlorides. A variety of cyclic and acyclic tetrasubstituted alpha,beta-unsaturated esters which included stereoisomerically pure compounds, a 2-substituted 3-aryl-2-cyclopentenone and naturally-occurring dihydrojasmone were cleanly synthesized by these smooth and selective cross-coupling reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

Synthesis of vinyl nonaflates derived from beta-ketoesters, beta-diketones and alpha-diketones and their palladium-catalyzed cross-coupling reactions with organozinc halides

BELLINA, FABIO;ROSSI, RENZO;
1999

Abstract

Cyclic and acyclic beta-ketoesters 4, a typical cyclic alpha-diketone 5 and a typical cyclic beta-diketone 6 were convened to the corresponding vinyl nonaflates of general formula 7, 8 and 9, respectively, by reaction with 1.2-1.5 equiv of NaH in DMF at 20-55 degrees C followed by treatment with 1.15-1.30 equiv of perfluoro-1-butanesulfonyl fluoride at 20 degrees C. These vinyl nonaflates, which were purified by MPLC on silica gel, proved to be excellent electrophiles in Pd-catalyzed cross-coupling reactions with aryl-, 1-alkynyl- and alkylzinc chlorides. A variety of cyclic and acyclic tetrasubstituted alpha,beta-unsaturated esters which included stereoisomerically pure compounds, a 2-substituted 3-aryl-2-cyclopentenone and naturally-occurring dihydrojasmone were cleanly synthesized by these smooth and selective cross-coupling reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.
Bellina, Fabio; Ciucci, D; Rossi, Renzo; Vergamini, P.
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: https://hdl.handle.net/11568/205051
 Attenzione

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

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 33
  • ???jsp.display-item.citation.isi??? 29
social impact