Journal
TETRAHEDRON
Volume 67, Issue 34, Pages 6206-6213Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.067
Keywords
Transfer hydrogenation; pH; Quinoxaline; Iridium; Tetrahydroquinoxaline
Categories
Funding
- National Natural Science Foundation of China [20873179, 20910102051]
- Renmin University of China
- Institute of Chemistry, the Chinese Academy of Sciences
- EPSRC [EP/G031444/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/G031444/1] Funding Source: researchfish
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The combination of [Cp*IrCl2](2) with N-(2-aminoethyl)-4-(trifluoromethyl)benzenesulfonamide constitutes an efficient catalyst for selective transfer hydrogenation of a variety of quinoxalines in water with HCOONa as the hydrogen source, affording the corresponding tetrahydroquinoxalines in good to excellent yields. The catalyst is air-stable, and the reduction could be performed without nitrogen protection. The aqueous phase reduction is shown to be highly pH-dependent, with acidic pH leading to better results. There exits a pH window for optimum rate, and the use of HOAc/NaOAc buffer solution is essential for maintaining a stable pH during the reaction. (C) 2011 Elsevier Ltd. All rights reserved.
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