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Synlett 2021; 32(12): 1192-1196
DOI: 10.1055/a-1520-2192
letter

Iron-Mediated Radical Nitrohalogenation Reactions of Enynes with tert-Butyl Nitrite

Yingming Ren‡
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
,
Yaxin Ge‡
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
,
Qinqin Yan∗
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
,
Yunfei Tian∗
b   College of Chemistry and Chemical Engineering, and Henan Key Laboratory of Function-Oriented Porous Materials, Luoyang Normal University, Luoyang, Henan 471934, P. R. of China
,
Jilai Wu
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
,
Yujie Yang
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
,
Lijun Li
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
,
Zejiang Li  ∗
a   Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, College of Chemistry and Environmental Science, Key Laboratory of Chemical Biology of Hebei Province, Hebei University, Baoding, Hebei 071002, P. R. of China
› Author AffiliationsThis project is supported by the National Natural Science Foundation of China (21702044), the Natural Science Foundation of Hebei Province (B2020201014), Science and Technology Project of Hebei Education Department (QN2019063), and the College Students Innovation and Entrepreneurship Training Program (2020286), Hebei University. We also thank the Key Scientific Research Project of Higher Education of Henan Province (No. 21A150038) and the Natural Science Foundation of Henan Province (162300410200) for their support.
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Abstract

A radical nitrohalogenation/cyclization of various enynes with tert-butyl nitrite has been developed that conveniently introduces useful nitro and halo groups into organic compounds. Some control experiments were performed to elucidate the mechanism. Further functional transformations proceeded well in this reaction system.

Key words

nitrohalogenation - cyclization - enynes - butyl nitrite - radical reaction - pyrrolidines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1520-2192.
  • Supporting Information


Publication History

Received: 20 February 2021

Accepted after revision: 28 May 2021

Accepted Manuscript online:
28 May 2021

Article published online:
15 June 2021

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