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Synlett 2023; 34(12): 1395-1398
DOI: 10.1055/s-0042-1751414
DOI: 10.1055/s-0042-1751414
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science
Ligand-Promoted Rosenmund–von Braun Reaction
Financial 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.
![](https://www.thieme-connect.de/media/synlett/202312/lookinside/thumbnails/st-2022-k0195-c_10-1055_s-0042-1751414-1.jpg)
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.
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
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References
- 1a Anbarasan P, Schareina T, Beller M. Chem. Soc. Rev. 2011; 40: 5049
- 1b Fleming FF, Yao L, Ravikumar PC, Funk L, Shook BC. J. Med. Chem. 2010; 53: 7902
- 1c Kalaria PN, Karad SC, Raval DK. Eur. J. Med. Chem. 2018; 158: 917
- 1d Kerru N, Singh P, Koorbanally N, Kumar V. Eur. J. Med. Chem. 2017; 142: 179
- 1e Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
- 1f Reddy RS, Lagishetti C, Kiran C, You H, He Y. Org. Lett. 2016; 18: 3818
- 1g Lagishetti C, Banne S, You H, Tang M, Guo J, Qi N, He Y. Org. Lett. 2019; 21: 5301
- 1h Reddy RS, Zheng S, Lagishetti C, You H, He Y. RSC Adv. 2016; 6: 68199
- 1i You H, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang X, Guo J, Wang C, He Y. J. Org. Chem. 2018; 83: 4119
- 2a Schareina T, Zapf A, Beller M. Chem. Commun. 2004; 1388
- 2b Yeung PY, So CM, Lau CP, Kwong FY. Org. Lett. 2011; 13: 648
- 2c Senecal TD, Shu W, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 10035
- 2d Cohen DT, Buchwald SL. Org. Lett. 2015; 17: 202
- 3 Zhang X, Xia A, Chen H, Liu Y. Org. Lett. 2017; 19: 2118
- 4a Zanon J, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 2890
- 4b Schareina T, Zapf A, Beller M. Tetrahedron Lett. 2005; 46: 2585
- 4c Schareina T, Zapf A, Mägerlein W, Müller N, Beller M. Chem. Eur. J. 2007; 13: 6249
- 5a Rosenmund KW, Struck E. Ber. Dtsch. Chem. Ges. B 1919; 52: 1749
- 5b von Braun J, Manz G. Justus Liebigs Ann. Chem. 1931; 488: 111
- 6a Mowry DT. Chem. Rev. 1948; 42: 189
- 6b Friedman L, Shechter H. J. Org. Chem. 1961; 26: 2522
- 6c Lindley J. Tetrahedron 1984; 40: 1433
- 7 Wang D, Kuang L, Li Z, Ding K. Synlett 2008; 69
- 8 Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
- 9a Zhou W, Fan M, Yin J, Jiang Y, Ma D. J. Am. Chem. Soc. 2015; 137: 11942
- 9b Fan M, Zhou W, Jiang Y, Ma D. Org. Lett. 2015; 17: 5934
- 9c De S, Yin J, Ma D. Org. Lett. 2017; 19: 4864
- 9d Gao J, Bhunia S, Wang K, Gan L, Xia S, Ma D. Org. Lett. 2017; 19: 2809
- 9e Bhunia S, Kumar V, Ma D. J. Org. Chem. 2017; 82: 12603
- 9f Pawar G, Wu H, De S, Ma D. Adv. Synth. Catal. 2017; 359: 1631
- 9g Chen Z, Ma D. Org. Lett. 2019; 21: 6874
- 9h Bhunia S, De S, Ma D. Org. Lett. 2022; 24: 1253
- 9i Li Q, Xu L, Ma D. Angew. Chem. Int. Ed. 2022; 62: e202210483
- 10a Fan M, Zhou W, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2016; 55: 6211
- 10b Xia S, Gan L, Wang K, Li Z, Ma D. J. Am. Chem. Soc. 2016; 138: 13493
- 10c Chen Z, Jiang Y, Zhang L, Guo Y, Ma D. J. Am. Chem. Soc. 2019; 141: 3541
- 11a Ma D, Niu S, Zhao J, Jiang X, Jiang Y, Zhang X, Sun T. Chin. J. Chem. 2017; 35: 1661
- 11b Zhao J, Niu S, Jiang X, Jiang Y, Zhang X, Sun T, Ma D. J. Org. Chem. 2018; 83: 6589
- 12 Chen Y, Xu L, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2021; 60: 7082
- 13 Klinkenberg JL, Hartwig JF. J. Am. Chem. Soc. 2012; 134: 5758
- 14 Ueda Y, Tsujimoto N, Yurino T, Tsurugi H, Mashima K. Chem. Sci. 2019; 10: 994
For selected references, see:
For selected references, see: