Practical and regioselective halonitrooxylation of olefins to access β-halonitrates

Xuan Cheng, Quan Yin, Yi-Fei Cheng, Shao-Hua Wu, Xin-Chang Sun, Kong De-Yi and Qing-Hai Deng ()
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Xuan Cheng: Shanghai Normal University
Quan Yin: Shanghai Normal University
Yi-Fei Cheng: Shanghai Normal University
Shao-Hua Wu: Shanghai Normal University
Xin-Chang Sun: Shanghai Normal University
Kong De-Yi: Shanghai Normal University
Qing-Hai Deng: Shanghai Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Organic nitrates, as effective donors of the signaling molecule nitric oxide, are widely applied in the pharmaceutical industry. However, practical and efficient methods for accessing organic nitrates are still scarce, and achieving high regiocontrol in unactivated alkene difunctionalization remains challenging. Here we present a simple and practical method for highly regioselective halonitrooxylation of unactivated alkenes. The approach utilizes TMSX (X: Cl, Br, or I) and oxybis(aryl-λ3-iodanediyl) dinitrates (OAIDN) as sources of halogen and nitrooxy groups, with 0.5 mol % FeCl3 as the catalyst. Remarkably, high regioselectivity in the halonitrooxylation of aromatic alkenes can be achieved even without any catalyst. This protocol features easy scalability and excellent functional group compatibility, providing a range of β-halonitrates (127 examples, up to 99% yield, up to >20:1 rr). Notably, 2-iodoethyl nitrate, a potent synthon derived from ethylene, reacts smoothly with a variety of functional units to incorporate the nitrooxy group into the desired molecules.

Date: 2024
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DOI: 10.1038/s41467-024-51655-5

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