Synthesis, Table of Contents Synthesis 2021; 53(24): 4614-4620DOI: 10.1055/a-1559-3346 feature Iodosulfonylation of Alkynes under Ultrasound Irradiation Chuanjiang Zhou , Xianghua Zeng ∗ Recommend Article Abstract Buy Article All articles of this category 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. Key words Key wordsultrasound - iodosulfonylation - alkynes - one-pot - green chemistry Full Text References References Selected examples: 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 Supplementary Material Supplementary Material Supporting Information
