Journal
CHEMCATCHEM
Volume 10, Issue 24, Pages 5627-5636Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201801525
Keywords
ADC reaction; ATH reaction; Recyclability; Ruthenium nanoparticles; Selectivity
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Funding
- National Natural Science Foundation of China [21471108, 21771131, 21531006, 21773163]
- State Key Laboratory of Organometallic Chemistry of Shanghai Institute of Organic Chemistry [2015kf-07]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
- Natural Science Foundation of Jiangsu Province [BK20161276]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201708]
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Ruthenium nanoparticles (NPs) supported on N-doped carbon (Ru/N-C) were prepared by the pyrolysis of cis-Ru(phen)(2)Cl-2 loaded onto carbon powder (VULCAN XC72R) at 800 degrees C. Ru/N-C NPs (0.2 mol% Ru) selectively catalyzed either acceptorless dehydrogenation coupling (ADC) or auto-transfer-hydrogen (ATH) reactions of amines with alcohols to imines and secondary amines. Such selectivity could be controlled by the choice of alkali metal ion associated with the base. Under similar catalytic conditions, the ADC cross-coupling of diamines with primary alcohols or diols afforded the corresponding benzimidazoles and quinoxalines in good to excellent yields. This catalytic system displayed good activity, recyclability, and wide applicability to a diverse range of substrates.
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