Palladium-catalyzed C(sp3)–H nitrooxylation of masked alcohols

Yuan Xue; Ruo-Bing Zhou; Jun Luo; Bing-Cheng Hu; Zhong-Quan Liu; Chao Jiang

doi:10.1039/D2OB01919A

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Palladium-catalyzed C(sp³)–H nitrooxylation of masked alcohols†

Yuan Xue,‡^a Ruo-Bing Zhou,‡^a Jun Luo,

*^a Bing-Cheng Hu,

*^a Zhong-Quan Liu

^b and Chao Jiang

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China
E-mail: chaojiang@njust.edu.cn, luojun@njust.edu.cn, hubc@njust.edu.cn

^b College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210023, China

Abstract

A palladium-catalyzed β-C(sp³)–H nitrooxylation of aliphatic alcohols with AgNO₂ is reported. An 8-formylquinoline-derived oxime is installed as an exo-type directing group for sp³ C–H activation and selectfluor acts as the oxidant. The reaction tolerates a variety of functional groups and shows good selectivity for β-C–H nitrooxylation of alcohols.

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Article information

DOI: https://doi.org/10.1039/D2OB01919A
Article type: Communication
Submitted: 20 Oct 2022
Accepted: 24 Nov 2022
First published: 25 Nov 2022

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Org. Biomol. Chem., 2023,21, 75-79

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Palladium-catalyzed C(sp³)–H nitrooxylation of masked alcohols

Y. Xue, R. Zhou, J. Luo, B. Hu, Z. Liu and C. Jiang, Org. Biomol. Chem., 2023, 21, 75 DOI: 10.1039/D2OB01919A

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Organic & Biomolecular Chemistry