IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Remarkable Reactivity of Boron-Substituted Furans in the Diels–Alder Reactions with Maleic Anhydride
Autor/es:
DEZOTTI, FEDERICO; DEZOTTI, FEDERICO; PELLEGRINET, SILVINA C.; PELLEGRINET, SILVINA C.; MEDRÁN, NOELIA S.; MEDRÁN, NOELIA S.
Revista:
ORGANIC LETTERS
Editorial:
AMER CHEMICAL SOC
Referencias:
Año: 2019 vol. 21 p. 5068 - 5072
ISSN:
1523-7060
Resumen:
The reactivity of boron-substituted furans as dienes in the Diels?Alder reaction with maleic anhydride has been investigated. Gratifyingly, the furans with boryl substituents at C-3 gave the exo cycloadduct exclusively with excellent yields. In particular, the potassium trifluoroborate exhibited outstanding reactivity at room temperature. Theoretical calculations suggested that the trifluoroborate group is highly activating and also that the thermodynamics is the main factor that determines whether the products can be obtained efficiently or not.
