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A Metal‐Organic Framework Brønsted Acid Catalyst: Synthesis, Characterization and Application to the Generation of Quinone Methides for [4+2] Cycloadditions
Author(s) -
Qi Chao,
Ramella Daniele,
Wensley Allison M.,
Luan Yi
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600364
Subject(s) - chemistry , catalysis , brønsted–lowry acid–base theory , cycloaddition , phenol , reagent , yield (engineering) , metal organic framework , selectivity , heterogeneous catalysis , organic chemistry , adsorption , materials science , metallurgy
Abstract A Brønsted acid‐derived metal‐organic framework (MOF) has been developed to serve as an efficient heterogeneous catalyst for a [4+2] cycloaddition. Aromatic sulfonyl groups were successfully installed using commercially available anhydridic reagents during post‐synthetic modifications. The MIL‐101‐NH‐RSO 3 H MOF catalyst was fully characterized by SEM, PXRD, FTIR, TGA and N 2 adsorption/desorption isotherm. Furthermore, a novel [4+2] cycloaddition of substituted 2‐vinyl‐substituted phenol was evaluated. The MIL‐101‐NH‐RSO 3 H catalyst showed superior catalytic capabilities when compared to a few other strong homogeneous Brønsted acid catalysts. The MIL‐101‐NH‐RSO 3 H catalyst is compatible with a variety of substituted substrates and it can be recycled five times without loss of yield or selectivity.