Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles
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ISSN: 1523-7060
E-ISSN: 1523-7052
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American Chemical Society
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Abstract
A novel route to 1,3-oxazaheterocycles based on cooperative Ru–H/Brønsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)3 complex allows for an efficient long distance chain-walking process while the Brønsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst.
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This is the peer reviewed version of the following article: Bernárdez, R., Suárez, J., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2016). Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles. Org. Lett., 18, 4, 642-645. [doi: 10.1021/acs.orglett.5b03499]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving.
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Bernárdez, R., Suárez, J., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2016). Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxa-zaheterocycles. Org. Lett., 18, 4, 642-645
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https://doi.org/10.1021/acs.orglett.5b03499Sponsors
This work was supported by MINECO (Spain) (projects CTQ2011-28258 and CTQ2014-59015R), Xunta de Galicia (project GRC2014/032) and the European Regional Development Fund (projects CTQ2014-59015R and GRC2014/032). R. B. thanks MEC for a predoctoral FPU fellowship and J. S. thanks XUGA for a postdoctoral contract. M. F.-M. thanks MINECO for a "Ramón y Cajal" contract
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Copyright © 2016 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving.