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Synlett 2023; 34(12): 1395-1398
DOI: 10.1055/s-0042-1751414
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science

Ligand-Promoted Rosenmund–von Braun Reaction

Quan Zhang
a   Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. of China
,
Dawei Ma∗
b   State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China
a   Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. of China
› Author AffiliationsFinancial support for this research from the Chinese Academy of Sciences (supported by the Strategic Priority Research Program, grant XDB20020200 & QYZDJ-SSW-SLH029) and the National Natural Science Foundation of China (Grant 21621002, 21831009 and 21991110) is acknowledged.
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Abstract

Two picolinamide ligands were found to have significant accelerating effect to classical Rosenmund–von Braun reaction, making the coupling of (hetero)aryl bromides with CuCN occur at 100–120 °C with good to excellent yields in most cases. A large number of functional groups and heterocycles were tolerated under these conditions, thereby providing a convenient and reliable approach for diverse synthesis of aryl nitriles.

Key words

aryl nitriles - cyanation - coupling reaction - ligand - copper cyanide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751414.
  • Supporting Information


Publication History

Received: 29 April 2022

Accepted after revision: 17 January 2023

Article published online:
09 February 2023

© 2023. Thieme. All rights reserved

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