Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
Open Access
- 19 December 2018
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 10 (7), 2193-2198
- https://doi.org/10.1039/c8sc04610g
Abstract
We report here a novel Ti3–BPDC metal–organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti–OH groups from neighboring SBUs point toward each other with an O–O distance of 2 Å, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ∼ 1980) and chemoselectivity.Keywords
Funding Information
- National Science Foundation (CHE-1464941)
- China Scholarship Council (201706310037)
- National Natural Science Foundation of China (21671162)
This publication has 46 references indexed in Scilit:
- Nonporous Titanium–Oxo Molecular Clusters That Reversibly and Selectively Adsorb Carbon DioxideInorganic Chemistry, 2013
- Mesoporous TiO2: Preparation, Doping, and as a Composite for PhotocatalysisChemCatChem, 2013
- Mesoporous titania: From synthesis to applicationNano Today, 2012
- A New Photoactive Crystalline Highly Porous Titanium(IV) DicarboxylateJournal of the American Chemical Society, 2009
- Synthesis of pharmaceutically active compounds containing a disubstituted piperidine frameworkBioorganic & Medicinal Chemistry, 2008
- Synthesis, Structure and Properties of Related Microporous N,N‘-Piperazinebismethylenephosphonates of Aluminum and TitaniumChemistry of Materials, 2006
- Metal@MOF: Loading of Highly Porous Coordination Polymers Host Lattices by Metal Organic Chemical Vapor DepositionAngewandte Chemie-International Edition, 2005
- Efficient Asymmetric Hydrogenation of PyridinesAngewandte Chemie-International Edition, 2004
- Homogeneous catalytic hydrogenation. 6. Synthetic and mechanistic aspects of the regioselective reductions of model coal nitrogen, sulfur, and oxygen heteroaromatic compounds using the (.eta.5-pentamethylcyclopentadienyl)rhodium tris(acetonitrile) dication complex as the catalyst precursorJournal of the American Chemical Society, 1992
- Characterization of the nature of surface sites on vanadia-titania catalysts by FTIRJournal of Catalysis, 1991