期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 49, 页码 18084-18092出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10768
关键词
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资金
- Office of Science, Office of Basic Energy Sciences, Division of Chemical Sciences, Geological and Biosciences of the US Department of Energy [DE-AC02-05CH11231]
Nanoparticles (Pd, Pt, Rh) stabilized by G4OH PAMAM dendrimers and supported in SBA-15 (MNPs/SBA-15 with M = Pd, Pt, Rh) were efficiently used as catalysts in the acceptorless dehydrogenation of tetrahydroquinoline/indoline derivatives in toluene (release of H-2) at 130 degrees C. These catalysts are air stable, very active, robust, and recyclable during the process. The reverse hydrogenation reaction of quinoline derivatives (H-2 storage) was also optimized and successfully performed in the presence of the same catalysts in toluene at 60 degrees C under only 1 atm of hydrogen gas. Such catalysts may be essential for the adoption of organic hydrogen-storage materials as an alternative to petroleum-derived fuels. Hot filtration test confirmed that the reaction follows a heterogeneous pathway. Moreover, PdNPs/SBA-15 was an excellent catalyst for the direct arylation at the C-2 position (via C-H activation) of indole in water in the presence of a hypervalent iodine oxidant. Thus, a one-pot dehydrogenation/direct arylation cascade reaction between indoline and an arylated agent was efficaciously performed in water, demonstrating the potential of the system to catalyze tandem heterogeneous/homogeneous processes by choice of the appropriate oxidant/reductant.
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