Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis
DOI: 10.1055/a-2723-2092
DOI: 10.1055/a-2723-2092
Paper
Cu(OAc)2/Vasicine-Catalyzed C–O Coupling of 2-Iodoanilides With MeOH
Authors
This work was financially supported by the National Natural Science Foundation of China (82360842, 82260830), Kuang Haixue Expert Workstation of Yunnan Province (202305AF150029), the Young and Middle-Aged Academic and Technological Leader of Yunnan (Grant 202405AC350042).
Supported by: Kuang Haixue Expert Workstation of Yunnan Province 202305AF150029
Supported by: National Natural Science Foundation of China 82260830,82360842
Abstract
The metal-catalyzed functionalization of o-haloanilides has become a popular research topic. In the present work, we have explored a practical Cu/vasicine-catalyzed Ullmann-type C–O coupling methodology of 2-iodoanilides with MeOH, which could regioselectively form 2-methoxylanilides.
Publication History
Received: 06 August 2025
Accepted after revision: 14 October 2025
Accepted Manuscript online:
14 October 2025
Article published online:
16 December 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Zhu R, Sun Q, Li J. et al. Chem Commun 2021; 57: 13190
- 1b Dimakos V, Taylor MS. Org Biomol Chem 2021; 19: 514
- 2 Tobisu M, Chatani N. Acc Chem Res 2015; 48: 1717
- 3a Aranyos A, Old DW, Kiyomori A, Wolfe JP, Sadighi JP, Buchwald SL. J Am Chem Soc 1999; 121: 4369
- 3b Rosen BM, Quasdorf KW, Wilson DA. et al. Chem Rev 2011; 111: 1346
- 4a Hartwig JF. Angew Chem Int Ed Engl 1998; 37 (15) 2046
- 4b Árvai C, Mika LTJ. Organomet Chem 2024; 1005: 122976
- 4c Strauss MJ, Greaves ME, Kim ST. et al. Angew Chem Int Ed 2024; 63: e202400333
- 4d Mohammadinezhad A, Akhlaghinia B. Catal Lett 2020; 150: 332
- 5 Szpera R, Isenegger PG, Ghosez M. et al. Org Lett 2020; 22: 6573
- 6 Zhu DL, Jiang S, Wu Q, Wang H, Li HY, Li HX. Org Lett 2021; 23: 8327
- 7 Quivelli AF, Marinò M, Vitale P, García-Álvarez J, Perna FM, Capriati V. ChemSusChem 2022; 15 (01) e202102211
- 8 Lindstedt E, Ghosh R, Olofsson B. Org Lett 2013; 15 (23) 6070
- 9a Mishra N, Singh AS, Agrahari AK, Singh SK, Singh M, Tiwari VK. ACS Comb Sci 2019; 21: 389
- 9b Györke G, Dancsó A, Volk B. et al. Tetrahedron Lett 2023; 116: 154319
- 9c Saranya TV, Sruthi PR, Anas S. Synth Commun 2019; 49 (02) 297
- 10a Diao X, Wang Y, Jiang Y, Ma D. J Org Chem 2009; 74: 7974
- 10b Tang YL, Li ML, Gao JC. et al. Tetrahedron Lett 2021; 69: 153001
- 11a Tan AS, Singh J, Rezali NS. et al. Molecules 2022; 27: 5373
- 11b Qadir M, Cobb J, Sheldrake PW. et al. J Org Chem 2005; 70: 1545
- 12a Liu G, Hao F, Liang L, Jin Z, Wu J. Org Lett 2023; 25: 2691
- 12b Liu Y, Wang Z, Zhao Z, Gao P, Ma N, Liu Q. Mol Catel 2021; 516: 111953
- 13a Zhao H, Fu H, Qiao R. J Org Chem 2010; 75: 3311
- 13b Kim T, Yang HY, Park BG. et al. Eur J Med Chem 2017; 175: 1172
- 14 Zhang Y, Du W, Zhu D. et al. Clin Immunol 2022; 244: 109102
- 15a Sharma S, Kumar M, Sharma S. et al. Org Biomol Chem 2016; 14: 8536
- 15b Sharma S, Kumar M, Bhatt V. et al. Tetrahedron Lett 2016; 57: 5003
- 16 Niu J, Zhou H, Li Z, Xu J, Hu S. J Org Chem 2008; 73 (19) 7814
- 17 Wolter M, Nordmann G, Job GE, Buchwald SL. Org Lett 2002; 4 (06) 973
- 18 Altman RA, Shafir A, Choi A, Lichtor PA, Buchwald SL. J Org Chem 2008; 73 (01) 284
- 19a Li MX, Li ML, Tang YL. et al. J Organomet Chem 2021; 943: 121844
- 19b Li M, Li M, Tang Y, Sun Y, Qu L, Mao Z. Curr Org Synth 2021; 18: 310
- 20 Li X, Qin D, Li Y, Mao Z. Synlett 2023; 34: 253
- 21 Nakamura I, Jo T, Ishida Y, Tashiro H, Terada M. Org Lett 2017; 19 (12) 3059
- 22 Mohammed I, Parai MK, Jiang X. et al. ACS Med Chem Lett 2012; 3 (06) 465
- 23 Fenwick NW, Telford R, Martin WHC, Bowen RD. Eur J Org Chem 2022; 24: e202200416
- 24 Lanier M, Schade D, Willems E. et al. J Med Chem 2012; 55 (02) 697