A Metal‐Organic Framework Brønsted Acid Catalyst: Synthesis, Characterization and Application to the Generation of Quinone Methides for [4+2] Cycloadditions. Issue 16 (3rd August 2016)

• Record Type: Journal Article
• Authors: Qi, Chao; Ramella, Daniele; Wensley, Allison M.; Luan, Yi
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 16(2016)
• Page Start: 2604
• Page End: 2611
• Publication Date: 2016-08-03
• Subjects: Brønsted acids -- [4+2] cycloaddition -- metal-organic frameworks -- post-synthetic modification -- quinone methides; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600364
• Languages: English
• ISSNs: 1615-4150

Abstract

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‐RSO3 H MOF catalyst was fully characterized by SEM, PXRD, FTIR, TGA and N2 adsorption/desorption isotherm. Furthermore, a novel [4+2] cycloaddition of substituted 2‐vinyl‐substituted phenol was evaluated. The MIL‐101‐NH‐RSO3 H catalyst showed superior catalytic capabilities when compared to a few other strong homogeneous Brønsted acid catalysts. The MIL‐101‐NH‐RSO3 H catalyst is compatible with a variety of substituted substrates and it can be recycled five times without loss of yield or selectivity. Abstract :