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Nitrohydroxylation of Olefins with Nitric Acid Using Tridentate NHC–Amidate–Alkoxide Containing Palladium Catalysts

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Abstract

In an attempt to explore the method of nitrohydroxylation which is fairly underdeveloped, our tridentate NHC–amidate–alkoxide containing palladium catalyst was used to nitrohydroxylate a variety of olefins in the presence of nitric acid. These reactions furnished β-nitro alcohols selectively to serve as a direct method for the synthesis of such compounds from various kinds of olefins. Dioxane served as an effective solvent, particularly in conjunction with TFA and AgNO3, which selectively generated the desired products. Vinyl arenes and other olefins produced a wide range of desired products in moderate to good yields.

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Authors and Affiliations

  1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1062, USA

    Justin O’Neill, Joo Ho Lee, Sungah Kim, Nima Zargari, Bijan Ketabchi, Jason Akahoshi, Felicia Yang & Kyung Woon Jung

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  1. Justin O’Neill
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  2. Joo Ho Lee
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  3. Sungah Kim
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  4. Nima Zargari
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  5. Bijan Ketabchi
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  6. Jason Akahoshi
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  7. Felicia Yang
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  8. Kyung Woon Jung
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Correspondence to Kyung Woon Jung.

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O’Neill, J., Lee, J.H., Kim, S. et al. Nitrohydroxylation of Olefins with Nitric Acid Using Tridentate NHC–Amidate–Alkoxide Containing Palladium Catalysts. Top Catal 61, 630–635 (2018). https://doi.org/10.1007/s11244-018-0915-4

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  • DOI: https://doi.org/10.1007/s11244-018-0915-4

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