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Squaramide‐IRMOF‐16 Analogue for Catalysis of Solvent‐Free, Epoxide Ring‐Opening Tandem and Multicomponent Reactions
Author(s) -
Vignatti Claudia,
LuisBarrera Javier,
Guillerm Vincent,
Imaz Inhar,
MasBallesté Rubén,
Alemán José,
Maspoch Daniel
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201801127
Subject(s) - squaramide , epoxide , tandem , chemistry , catalysis , ring (chemistry) , yield (engineering) , cascade reaction , combinatorial chemistry , organocatalysis , amine gas treating , solvent , organic chemistry , enantioselective synthesis , materials science , metallurgy , composite material
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.