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Synlett 2022; 33(10): 969-972
DOI: 10.1055/a-1804-7546
letter

Rh(III)-Catalyzed Synthesis of 2-Nitro-2H-azirines via sp3 C–H Activation

Xiaojun Huang
a   College of Materials Science and Engineering, Nanjing Tech University, Nanjing 211816, P. R. of China
,
Yun Ge
b   Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. of China
,
Yang Qian
c   College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
,
Zhengyu Zhang  ∗
c   College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, P. R. of China
› Author AffiliationsThe authors gratefully acknowledge funding from Jiangsu Students’ Platform for Innovation and Entrepreneurship Training Program and the Starting Funding of Research from Nanjing Tech University.
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Abstract

An expedient Rh(III)-catalytic method has been described to synthesis of 2-nitro-2H-azirine derivatives from easily accessible β-nitrooxime ethers via sp3 C–H activation process. This protocol features of low catalyst loading, very mild reaction conditions, and tolerating a diverse of functionalities in good yields. A possible reaction pathway is proposed involving [RhCp*Cl2]2-catalyzed sp3 C–H bond activation and pivalic acid elimination steps.

Key words

Rh(III) - 2-nitro-2H-azirine - derivatives - β-nitrooxime - sp3 C–H

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1804-7546.
  • Supporting Information


Publication History

Received: 14 February 2022

Accepted after revision: 22 March 2022

Accepted Manuscript online:
22 March 2022

Article published online:
10 May 2022

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