RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2021; 53(21): 4086-4096
DOI: 10.1055/a-1541-6271
DOI: 10.1055/a-1541-6271
paper
Direct and Efficient Synthesis of Sulfonium Acyl Sulfonylmethylide Ylides from Acetylenic Sulfones and Dimethyl Sulfoxide
This work was supported partially from the National Natural Science Foundation of China (nos. 21772010 and 21572017) and the Fundamental Research Funds for the Central Universities (XK1802-6).
Abstract
Bifunctionalized sulfonium ylides – sulfonium acyl sulfonylmethylides – were directly and efficiently prepared from various acetylenic sulfones and aliphatic sulfoxides under heating conditions. The current method features short reaction time, low cost, readily available starting materials, convenient operation, and purification, providing an efficient access to widely applied bifunctionalized sulfonium ylides.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1541-6271.
- Supporting Information
Publikationsverlauf
Eingereicht: 24. Mai 2021
Angenommen nach Revision: 30. Juni 2021
Accepted Manuscript online:
30. Juni 2021
Artikel online veröffentlicht:
29. Juli 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Leng H.-J, Li Q.-Z, Xiang P, Qi T, Dai Q.-S, Jia Z.-Q, Gou C, Zhang X, Li J.-L. Org. Lett. 2021; 23: 1451
- 1b Yuan F, Yan D.-M, Gao P.-P, Shi D.-Q, Xiao W.-J, Chen J.-R. ChemCatChem 2021; 13: 543
- 1c Zhou F, Cheng Y, Liu X.-P, Chen J.-R, Xiao W.-J. Chem. Commun. 2019; 55: 3117
- 1d Lu L.-Q, Li T.-R, Wang Q, Xiao W.-J. Chem. Soc. Rev. 2017; 46: 4135
- 1e Aggarwal VK, Winn CL. Acc. Chem. Res. 2004; 37: 611
- 2a Li Q.-Z, Jia Z.-Q, Chen L, Zhang X, Leng H.-J, Zeng R, Liu Y.-Q, Zou W.-L, Li J.-L. Org. Lett. 2021; 23: 814
- 2b Dong J, Du H, Xu J. J. Org. Chem. 2019; 84: 10724
- 2c Nambu H, Onuki Y, Ono N, Tsuge K, Yakura T. Chem. Commun. 2019; 55: 6539
- 2d Dong J, Xu J. Org. Biomol. Chem. 2017; 15: 836
- 3a Liu X, Shao Y, Sun J. Org. Lett. 2021; 23: 1038
- 3b Li L, Yang M, He Q, Fan R. Nat. Commun. 2020; 11: 4805
- 3c Bisag GD, Ruggieri S, Fochi M, Bernardi L. Org. Biomol. Chem. 2020; 18: 8793
- 3d Ahire MM, Thoke MB, Mhaske SB. Org. Lett. 2018; 20: 848
- 3e Guo W, Luo Y, Sung HH. Y, Williams ID, Li P, Sun J. J. Am. Chem. Soc. 2020; 142: 14384
- 3f Li J, He H, Huang M, Chen Y, Luo Y, Yan K, Wang Q, Wu Y. Org. Lett. 2019; 21: 9005
- 4a Li P. Synlett 2021; 32: in press
- 4b Knittl-Frank C, Saridakis I, Stephens T, Gomes R, Neuhaus J, Misale A, Oost R, Oppedisano A, Maulide N. Chem. Eur. J. 2020; 26: 10972
- 4c Qin H, Jia Y, Wang N, Jiang Z.-X, Yang Z. Chem. Commun. 2020; 56: 8265
- 4d Oost R, Neuhaus JD, Misale A, Meyrelles R, Veiros LF, Maulide N. Chem. Sci. 2018; 9: 7091
- 5a Wang N, Saidhareddy P, Jiang X. Nat. Product Rep. 2020; 37: 246
- 5b Liu H, Jiang X. Chem. Asian J. 2013; 8: 2546
- 6a Speziale AJ, Tung CC, Ratts KW, Yao A. J. Am. Chem. Soc. 1965; 87: 3460
- 6b Corey EJ, Chaykovsky M. J. Am. Chem. Soc. 1965; 87: 1353
- 7a Katayama S, Watanabe T, Yamauchi M. Chem. Pharm. Bull. 1990; 38: 3314
- 7b Schank K, Schuhknecht C. Synthesis 1978; 678
- 7c Cook AF, Moffatt JG. J. Am. Chem. Soc. 1968; 90: 740
- 8a Vaitla J, Hopmann KH, Bayer A. Org. Lett. 2017; 19: 6688
- 8b Huang X, Patil M, Farès C, Thiel W, Maulide N. J. Am. Chem. Soc. 2013; 135: 7312
- 8c Huang X, Goddard R, Maulide N. Angew. Chem. Int. Ed. 2010; 49: 8979
- 8d Illger W, Liedhegener A, Regitz M. Justus Liebigs Ann. Chem. 1972; 760: 1
- 8e Lu J, Li L, He X.-K, Xu G.-Y, Xuan J. Chin. J. Chem. 2021; 39: 1646
- 8f Ando W, Yagihara T, Tozune S, Imai I, Suzuki J, Toyama T, Nakaido S, Migita T. J. Org. Chem. 1972; 37: 1721
- 9a Fu D, Dong J, Du H, Xu J. J. Org. Chem. 2020; 85: 2752
- 9b Tashrifi Z, Khanaposhtani MM, Larijani B, Mahdavi M. Adv. Synth. Catal. 2019; 362: 65
- 9c Magolan J, Jones-Mensah E, Karki M. Synthesis 2016; 48: 1421
- 9d Wu X.-F, Natte K. Adv. Synth. Catal. 2016; 358: 336
- 9e Rather SA, Kumar A, Ahmed QN. Chem. Commun. 2019; 55: 4511
- 9f Zhao P, Wu X, Geng X, Wang C, Zhou Y, Wu Y.-D, Wu A.-X. J. Org. Chem. 2019; 84: 8322
- 9g Xu N, Zhang Y, Chen W, Li P, Wang L. Adv. Synth. Catal. 2018; 360: 1199
- 10 Xu J, Fu D, Dong J, Wang J. Asian J. Org. Chem. 2021; 16: in press
- 11a Hanack M, Wilhelm B. Angew. Chem., Int. Ed. Engl. 1989; 28: 1057
- 11b Chow TJ, Tan U.-K, Peng S.-M. Synth. Commun. 1988; 18: 519
- 12 Meesin J, Katrun P, Pareseecharoen C, Pohmakotr M, Reutrakul V, Soorukram D, Kuhakarn C. J. Org. Chem. 2016; 81: 2744
- 13 Qi D, Dong W, Peng Z, Zhang Y, An D. Tetrahedron 2019; 75: 130427
- 14 Suryakiran N, Reddy TS, Ashalatha K, Lakshman M, Venkateswarlu Y. Tetrahedron Lett. 2006; 47: 3853
- 15 Dong J, Du H, Xu J. RSC Adv. 2019; 9: 25034
- 16 Meng X, Xu H, Cao X, Cai XM, Luo J, Wang F, Huang S. Org. Lett. 2020; 22: 6827
- 17 Dai C, Wang J, Deng S, Zhou C, Zhang W, Zhu Q, Tang X. RSC Adv. 2017; 7: 36112
- 18 Yoshida Z, Ogoshi H, Tokumitsu T. Tetrahedron 1970; 26: 2987