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Synthesis 2022; 54(03): 655-657
DOI: 10.1055/a-1648-7074
DOI: 10.1055/a-1648-7074
psp
A Convenient Procedure for Sonogashira Reactions Using Propyne
Authors
This work was supported by the U.S. Department of Energy (DOE), Office of Biological and Environmental Research, Biological Systems Science Division under FWP# AL-18-380-055 to the Ames Laboratory. The Ames Laboratory is operated for the U.S. Department of Energy by Iowa State University under Contract No. DE-AC02-07CH11358.

Abstract
A modified Sonogashira coupling of aryl iodides and propyne was achieved using only two equivalents of propyne in THF from –78 °C to room temperature.
Publication History
Received: 19 August 2021
Accepted after revision: 20 September 2021
Accepted Manuscript online:
20 September 2021
Article published online:
21 October 2021
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References
- 1 Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
- 2 Yang Q, Babij NR, Good S. Org. Process Res. Dev. 2019; 23: 2608
- 3a Zhang W, Kraft S, Moore JS. J. Am. Chem. Soc. 2004; 126: 329
- 3b Kim JT, Butt J, Gevorgyan V. J. Org. Chem. 2004; 69: 5638
- 3c Nelson ML, Ismail MY, McIntyre L, Bhatia B, Viski P, Rennie G, Andorsky D, Messersmith D, Stapleton K, Dumornay J. J. Org. Chem. 2003; 68: 5838
- 3d Berliner MA, Cordi EM, Dunetz JR, Price KE. Org. Process Res. Dev. 2010; 14: 180
- 3e Rudyanto M, Tomizawa Y, Morita H, Honda T. Org. Lett. 2008; 10: 1921
- 4 Capani JS, Cochran JE, Liang J. J. Org. Chem. 2019; 84: 9378
- 5 Abraham E, Suffert J. Synlett 2002; 328
- 6 Torigoe T, Ohmura T, Suginome M. Chem. Eur. J. 2016; 22: 10415
- 7 Znidar D, Hone CA, Inglesby P, Boyd A, Kappe CO. Org. Process Res. Dev. 2017; 21: 878
- 8 Nakamura K, Okubo H, Yamaguchi M. Synlett 1999; 549
- 9 Kim JH, Song T, Chung YK. Org. Lett. 2017; 19: 1248
- 10 Engler TA, Combrink KD, Ray JE. Synth. Commun. 1989; 19: 1735
- 11 Malpani YR, Biswas BK, Han HS, Jung YS, Han SB. Org. Lett. 2018; 20: 1693
- 12 Cruz FA, Dong VM. J. Am. Chem. Soc. 2017; 139: 1029
- 13 Zhang Q, Shi C, Zhang HR, Wang KK. J. Org. Chem. 2000; 65: 7977
- 14 Iqbal N, Iqbal N, Maiti D, Cho EJ. Angew. Chem. Int. Ed. 2019; 58: 15808
- 15 Alterman JL, Vang DX, Stroud MR, Halverson LJ, Kraus GA. Org. Lett. 2020; 22: 7424