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Synthesis 2023; 55(17): 2702-2712
DOI: 10.1055/a-2096-7045
paper

A Nickel(II) Chloride and Tetrahydroxydiboron Cocatalyzed Facile Synthesis of Benzo[b]azepines with an Appended Fluorinated Side Chain

Wenqing Lei
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Yingfan Yang
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Minjie Guo
b   Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Wentao Zhao∗
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Guangwei Wang  ∗
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
› Author AffiliationsThe authors are grateful for the financial support from the National Natural Science Foundation of China (No. 22271214).
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Abstract

A novel nickel-catalyzed chemoselective cascade reaction strategy towards the synthesis of benzo[b]azepines was developed. The method is characterized by simple and mild conditions, low cost, and a wide range of substrates. This method enabled the facile and efficient synthesis of a series of 2,3,4,5-tetrahydro-1H-benzo[b]azepine analogues with an appended fluorinated side chain.

Key words

tetrahydroxydiboron - ethyl bromodifluoroacetate - nickel catalyst - radical cascade - benzo[b]azepines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2096-7045.
  • Supporting Information


Publication History

Received: 19 April 2023

Accepted after revision: 22 May 2023

Accepted Manuscript online:
22 May 2023

Article published online:
19 June 2023

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