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Synthesis 2021; 53(24): 4614-4620
DOI: 10.1055/a-1559-3346
DOI: 10.1055/a-1559-3346
feature
Iodosulfonylation of Alkynes under Ultrasound Irradiation
This research work was supported by the National Natural Science Foundation of Zhejiang Province (Grant No. LY17B030011).
Abstract
(E)-β-Iodo vinylsulfones are synthesized under ultrasound irradiation using alkynes, sulfonyl hydrazides, potassium iodide and hydrogen peroxide. The key features of this protocol are the speed and efficiency of the reactions, which afford good to excellent yields of the desired products by employing ultrasound as the driving force. Mechanistic studies reveal that a sulfonyl radical intermediate is generated via sulfonyl iodide homolysis.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1559-3346.
- Supporting Information
Publication History
Received: 05 July 2021
Accepted after revision: 27 July 2021
Accepted Manuscript online:
27 July 2021
Article published online:
01 September 2021
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References
- 1a Fang Y, Luo Z, Xu X. RSC Adv. 2016; 6: 59661
- 1b Wille U. Chem. Rev. 2013; 113: 813
- 1c Liu NW, Liang S, Manolikakes G. Synthesis 2016; 48: 1939
- 1d Meadows DC, Gervay-Hague J. Med. Res. Rev. 2006; 26: 793
- 1e Back TG, Clary KN, Gao D. Chem. Rev. 2010; 110: 4498
- 1f Simpkins NS. Tetrahedron 1990; 46: 6951
- 1g Huo Y.-M, Zeng H.-P, Jiang H.-F. Chin. J. Org. Chem. 2006; 26: 239
- 1h Nair V, Augustine A, Suja TD. Synthesis 2002; 2259
- 1i Xiong Y, Zhang J, Shen Q, Huang J, Wang T. Chin. J. Org. Chem. 2021; 41: 2735
- 1j Sun K, Shi Z.-D, Liu Z.-H, Luan B.-X, Zhu J.-L, Xue Y.-R. Org. Lett. 2018; 20: 6687
- 2 Palmer JT, Rasnick D, Klaus JL, Bromme D. J. Med. Chem. 1995; 38: 3193
- 3 Meadows DC, Sanchez T, Neamati N, North TW, Gervay-Hague J. Bioorg. Med. Chem. 2007; 15: 1127
- 4a Jia J, Ho YA, Bulow RF, Rueping M. Chem. Eur. J. 2018; 24: 14054
- 4b Shameem MA, Esfandiarfard K, Öberg E, Ott S, Orthaber A. Chem. Eur. J. 2016; 22: 10614
- 4c Bull JR, Desmond-Smith NS, Heggie SJ, Hunter R, Tien F.-C. Synlett 1998; 900
- 4d Iwata N, Morioka T, Kobayashi T, Asada T, Kinoshita H, Inomata K. Bull. Chem. Soc. Jpn. 1992; 65: 1379
- 4e Truce WE, Wolf GC. J. Org. Chem. 1971; 36: 1727
- 5a Liang Y, Suzol SH, Wen Z, Artiles AG, Mathivathanan L, Raptis RG, Wnuk SF. Org. Lett. 2016; 18: 1418
- 5b Zoller T, Uguen D. Eur. J. Org. Chem. 1999; 1545
- 5c Padwa A, Austin DJ, Ishida M, Muller CL, Murphree SS, Yeske PE. J. Org. Chem. 1992; 57: 1161
- 5d Truce WE, Borel AW, Marek PJ. J. Org. Chem. 1976; 41: 401
- 6a Zhang J, Liang Z, Wang J, Guo Z, Liu C, Xie M. ACS Omega 2018; 3: 18002
- 6b Sun Y, Abdukader A, Lu D, Zhang H, Liu C. Green Chem. 2017; 19: 1255
- 6c Gao Y, Wu W, Huang Y, Huang K, Jiang H. Org. Chem. Front. 2014; 1: 361
- 7a Gu X, Xie M, Zhao X, Sun Y, Zhang W, Xie F, Wang S. Chin. J. Chem. 2008; 26: 1625
- 7b Wei W, Wen J, Yang D, Jing H, You J, Wang H. RSC Adv. 2015; 5: 4416
- 7c Wan JP, Hu D, Bai F, Wei L, Liu Y. RSC Adv. 2016; 6: 73132
- 8 Luo D, Min L, Zheng W, Shan L, Wang X, Hu Y. Chin. Chem. Lett. 2020; 31: 1877
- 9 Li X, Xu X, Shi X. Tetrahedron Lett. 2013; 54: 3071
- 10 Taniguchi N. Tetrahedron 2018; 74: 1454
- 11 Ma Y, Wang K, Zhang D, Sun P. Adv. Synth. Catal. 2019; 361: 597
- 12 Hou Y, Zhu L, Hu H, Chen S, Li Z, Liu Y, Gong P. New J. Chem. 2018; 42: 8752
- 13a Turhan K, Ozturkcan SA, Uluer M, Turgut Z. Acta Chim. Slov. 2014; 61: 623
- 13b Hosseinnia R, Mamaghani M, Tabatabaeian K, Shirini F, Rassa M. Bioorg. Med. Chem. Lett. 2012; 22: 5956
- 13c Safari J, Javadian L. Ultrason. Sonochem. 2015; 22: 341
- 13d Wang J, Bai X, Xu C, Wang Y, Lin W, Zou Y, Shi D. Molecules 2012; 17: 8674
- 13e Dandia A, Singh R, Bhaskaran S, Samant SD. Green Chem. 2011; 13: 1852
- 14 Mason TJ. Chem. Soc. Rev. 1997; 26: 443
- 15 Banerjee B. Ultrason. Sonochem. 2017; 35: 1
- 16a Li J.-T, Sun S.-F, Sun M.-X. Ultrason. Sonochem. 2011; 18: 42
- 16b Thari FZ, Tachallait H, Alaoui N, Talha A, Arshad S, Álvarez E, Karrouchi K, Bougrin K. Ultrason. Sonochem. 2020; 68: 10522
- 17a Wu C, Lu L.-H, Peng A.-Z, Jia G.-K, Peng C, Cao Z, Tang Z, He W.-M, Xu X. Green Chem. 2018; 20: 3683
- 17b Wu C, Hong L, Shu H, Zhou Q.-H, Wang Y, Su N, Jiang S, Cao Z, He W.-M. ACS Sustainable Chem. Eng. 2019; 7: 8798
- 18a Zeng X, Chen L. Org. Biomol. Chem. 2018; 16: 7557
- 18b Zeng X, Chen L. Org. Biomol. Chem. 2019; 17: 3338
- 18c Zhang M, Zeng X. Org. Lett. 2021; 23: 3326
- 19 Kadari L, Palakodety RK, Yallapragada LP. Org. Lett. 2017; 19: 2580
- 20 Roscoe TH, Peterson CA, Lippincott DJ, Jette CI, Lipshutz BH. Angew. Chem. Int. Ed. 2014; 53: 4159
- 21 Meesin J, Katrun P, Pareseecharoen C, Pohmakotr M, Reutrakul V, Soorukram D, Kuhakarn C. J. Org. Chem. 2016; 81: 2744
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