A novel synthesis of 2-[(dialkylcarbamoyl)methylene]tetrahydrofuran derivatives 3-8 by Pd-catalyzed oxidative carbonylation of 4-yn-1-ols 1 in the presence of dialkylamines 2 is reported (2:1 molar ratio = 2). Reactions are carried out in 1,2- dimethoxyethane (DME) at 100 °C and under 20 atm (at 25 °C) of a 4:1 mixture of CO and air, in the presence of catalytic amounts of PdI2 (1 mol % with respect to 1) in conjunction with 10 equiv. of KI. Formation of 3-8 occurs through Pd-catalyzed oxidative monoaminocarbonylation of the triple bond of 1 to give 6-hydroxy-2-ynamide intermediates 9, followed by stereoselective conjugate addition of the hydroxyl group to the triple bond.

A NEW SYNTHESIS OF 2-[(DIALKYLCARBAMOYL)METHYLENE]TETRAHYDROFURAN DERIVATIVES BY PD-CATALYZED OXIDATIVE AMINOCARBONYLATION OF 4-YN-1-OLS

GABRIELE, Bartolo;
2004-01-01

Abstract

A novel synthesis of 2-[(dialkylcarbamoyl)methylene]tetrahydrofuran derivatives 3-8 by Pd-catalyzed oxidative carbonylation of 4-yn-1-ols 1 in the presence of dialkylamines 2 is reported (2:1 molar ratio = 2). Reactions are carried out in 1,2- dimethoxyethane (DME) at 100 °C and under 20 atm (at 25 °C) of a 4:1 mixture of CO and air, in the presence of catalytic amounts of PdI2 (1 mol % with respect to 1) in conjunction with 10 equiv. of KI. Formation of 3-8 occurs through Pd-catalyzed oxidative monoaminocarbonylation of the triple bond of 1 to give 6-hydroxy-2-ynamide intermediates 9, followed by stereoselective conjugate addition of the hydroxyl group to the triple bond.
2004
Carbonylation; Tetrahydrofurans; Palladium; Heterocycles
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/20.500.11770/143804
 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??? 21
social impact