Palladium‐Catalyzed CH Bond Functionalization of a Metal–Organic Framework (MOF): Mild, Selective, and Efficient

Dröge, Thomas; Notzon, Andreas; Fröhlich, Roland; Glorius, Frank

doi:10.1002/chem.201101850

Cited by 30 publications

(11 citation statements)

References 67 publications

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“…Glorius reported the late-stage phenylation of N-methylindoles to modify a rod moiety of a metal-organic framework (MOF). [24] The Pd-catalyzed arylation of indoles [25] was applied to the MOF UMCM-1 (University of Michigan Crystalline Material-1; 26) synthesized from N-methylindole-4,7-dicarboxylic acid (24), 1,3,5-tris(4-carboxyphenyl)benzene (25), and zinc(II) nitrate. After evaluation of the reaction conditions, the authors found that dimethylformamide (DMF) was a good solvent for the C-H phenylation of N-methylindole moieties without decomposition of the MOF structure (Scheme 9).…”

Section: Azolesmentioning

confidence: 99%

Synthesis of Extended π‐Systems through C–H Activation

2014

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Activation of aromatic CH bonds by a transition metal catalyst has received significant attention in the synthetic chemistry community. In recent years, rapid and site-selective extension of π-electron systems by C-H activation has emerged as an ideal methodology for preparing organic materials with extended π-systems. This Review focuses on recently reported π-extending C-H activation reactions directed toward new optoelectronic conjugated materials.

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Section: Azolesmentioning

confidence: 99%

Synthesis of Extended π‐Systems through C–H Activation

2014

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“…Post- or presynthetic functionalization of MOFs is a very promising area of MOF research [109,110,111,112,113,114,115,116,117,118,119,120,121,122,123,124,125,126]. Ahnfeldt et al [125] made use of solid-state heteronuclear 1 H– 15 N, 1 H– 13 C, and homonuclear 1 H– 1 H correlation spectroscopy in order to prove the methylation of NH 2 groups in Christian-Albrechts-University-1 (CAU-1) derivatives.…”

Section: Characterization Of the Mof Latticementioning

confidence: 99%

Solid-State NMR Spectroscopy of Metal–Organic Framework Compounds (MOFs)

et al. 2012

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Nuclear Magnetic Resonance (NMR) spectroscopy is a well-established method for the investigation of various types of porous materials. During the past decade, metal–organic frameworks have attracted increasing research interest. Solid-state NMR spectroscopy has rapidly evolved into an important tool for the study of the structure, dynamics and flexibility of these materials, as well as for the characterization of host–guest interactions with adsorbed species such as xenon, carbon dioxide, water, and many others. The present review introduces and highlights recent developments in this rapidly growing field.

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“…Glorius and co-workers developed a method for the direct C-H arylation of indole-derived UMCM-1 (University of Michigan Crystalline Material-1)type MOF in the presence of a palladium catalyst (Scheme 76). 112,113 The phenylated UMCM-1-Ph-indole showed better nitrogen absorption and desorption abilities than the original UMCM-1-indole.…”

Section: Scheme 75 Synthesis Of Pentabenzoazacorannulene Via 13-dipomentioning

confidence: 99%

C–H Bond Transformations Leading to the Synthesis of Organic Functional Materials

Kuninobu

Sueki

2015

Synthesis

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In this review, transition-metal-catalyzed or-mediated C-H transformations leading to the synthesis of organic functional materials, such as oligomers, polymers, and π-conjugated molecules, are summarized. 1 Introduction 2 Oligomers and Polymers 2.1 Synthesis of Oligomers and Polymers 2.2 Chemical Modification of Polymers 3 π-Conjugated Molecules 3.1 Indenes and Fluorenes 3.2 Acenes 3.3 Triphenylenes 3.4 Chemical Modification of Perylene Diimides 3.5 Nanographenes 3.6 Condensed Polycyclic π-Conjugated Molecules with Five-Membered Heteroaromatic Rings 3.7 π-Conjugated Molecules with Nitrogen-Containing Six-Membered Heteroaromatics 3.8 Porphyrins 3.9 Miscellaneous (π-Conjugated Molecules) 4 Miscellaneous (Excluding Polymers and π-Conjugated Molecules) 5 Outlook and Conclusions

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Palladium‐Catalyzed CH Bond Functionalization of a Metal–Organic Framework (MOF): Mild, Selective, and Efficient

Cited by 30 publications

References 67 publications

Synthesis of Extended π‐Systems through C–H Activation

Synthesis of Extended π‐Systems through C–H Activation

Solid-State NMR Spectroscopy of Metal–Organic Framework Compounds (MOFs)

C–H Bond Transformations Leading to the Synthesis of Organic Functional Materials

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