Squaramide-IRMOF-16 analogue for catalysis of solvent-free, epoxide ring-opening tandem and multicomponent reactions

Tandem and multicomponent one-pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side-products. Herein we report the use of metal-organic framew...

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Detalles Bibliográficos
Autores: Vignatti Abellan, Claudia|||0000-0003-3462-0251, Luis-Barrera, Javier, Guillerm, Vincent|||0000-0003-3460-223X, Imaz, Inhar|||0000-0002-0278-1141, Mas Balleste, Ruben|||0000-0003-1988-8700, Aleman Lara, Jose Julian|||0000-0003-0164-1777, Maspoch Comamala, Daniel|||0000-0003-1325-9161
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:203031
Acceso en línea:https://ddd.uab.cat/record/203031
https://dx.doi.org/urn:doi:10.1002/cctc.201801127
Access Level:acceso abierto
Palabra clave:Metal-organic frameworks
H-bond catalysis
Tandem and multicomponent reactions
Squaramide
Descripción
Sumario:Tandem and multicomponent one-pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side-products. Herein we report the use of metal-organic framework (MOF) pores decorated with organocatalytic squaramide moieties to confine ring-opening epoxide reactions of diverse substrates. Controlled mono-addition or tandem reactions inside the pores yield 1,2-aminoalcohols or 1,2,2'-aminodialcohols, respectively, in good yields. In addition, this squaramide-functionalised MOF enables catalysis of higher-complexity multicomponent reactions such as the catalytic ring-opening of two different epoxides by a single amine to afford 1,2,2'-aminodialcohols.