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
Synthesis 2022; 54(16): 3588-3594
DOI: 10.1055/a-1820-2475
DOI: 10.1055/a-1820-2475
paper
Copper-Catalyzed Direct C(sp2)–H Sulfuration of Aryl Alkenes by Using Tetraalkylthiuram Disulfides for the Synthesis of Alkenyl Dithiocarbamates
This work was supported by the National Natural Science Foundation of China (Grant No. 21702059), Shanghai Pujiang Program (Grant No. 18PJ1402200), and Fundamental Research Funds for the Central Universities (Grant Nos. 222201814014, JKVJ1211010, and JKVJ12001010).
Abstract
Copper-catalyzed direct C(sp2)–H sulfuration of aryl alkenes by using tetraalkylthiuram disulfides as sulfuration reagents has been developed. The reaction provides an efficient method for the synthesis of a variety of alkenyl dithiocarbamates, which are important structure motifs widely applied in materials, pharmaceuticals, and agrochemicals.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1820-2475.
- Supporting Information
Publication History
Received: 25 February 2022
Accepted after revision: 07 April 2022
Accepted Manuscript online:
07 April 2022
Article published online:
17 May 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Mansouri-Torshizi H, Saeidifar M, Divsalar A, Saboury AA. Spectrochim. Acta, Part A 2010; 7: 312
- 1b Horita Y, Takii T, Kuroishi R, Chiba T, Ogawa K, Kremer L, Sato Y, Lee Y, Hasegawa T, Onozaki K. Bioorg. Med. Chem. Lett. 2011; 21: 899
- 1c Kamal A, Sathish M, Nayak VL, Srinivasulu V, Kavitha B, Tangella Y, Thummuri D, Bagul C, Shankaraiah N, Nagesh N. Bioorg. Med. Chem. 2015; 23: 5511
- 1d Zhang E, Jiao W.-W, Wang S, Xu J.-M, Shi X.-J, Wang Y.-C, Wang Y.-N, Liu H.-M. Med. Chem. Res. 2016; 25: 3011
- 1e Fu D.-J, Zhang S.-Y, Liu Y.-C, Zhang L, Liu J.-J, Song J, Zhao R.-H, Li F, Sun H.-H, Liu H.-M, Zhang Y.-B. Bioorg. Med. Chem. Lett. 2016; 26: 3918
- 1f Bakthavatsalam S, Wiangnak P, George DJ, Zhang T, Franz KJ. Bioorg. Med. Chem. Lett. 2020; 30: 127148
- 1g Tan W, Jänsch N, Öhlmann T, Meyer-Almes F, Jiang X. Org. Lett. 2019; 21: 7484
- 1h Tan W, Wang C, Jiang X. Org. Chem. Front. 2018; 5: 2390
- 1i Feng M, Tang B, Liang S, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
- 2 Kamble A, Kamble R, Dodamani S, Jalalpure S, Rasal V, Kumbar M, Joshi S, Dixit S. Arch. Pharmacal Res. 2017; 40: 444
- 3 Salmi-Mani H, Ait-Touchente Z, Lamouri A, Carbonnier B, Caron J.-F, Benzarti K, Chehimi MM. RSC Adv. 2016; 6: 88126
- 4 Horita Y, Takii T, Chiba T, Kuroishi R, Maeda Y, Kurono Y, Inagaki E, Nishimura K, Yamamoto Y, Abe C, Mori M, Onozaki K. Bioorg. Med. Chem. Lett. 2009; 19: 6313
- 5 Wakamori S, Yoshida Y, Ishii Y. Agric. Biol. Chem. 1969; 33: 1367
- 6a Hu J, Ye X, Hao S, Zhao Q, Zhao M, Wei Y, Wu Z, Wang N, Ji X. Asian J. Org. Chem. 2020; 9: 2191
- 6b Lai M, Wu Z, Su F, Yu Y, Jing Y, Kong J, Wang Z, Wang S, Zhao M. Eur. J. Org. Chem. 2020; 2020: 198
- 6c Lai M, Wu Z, Wang Y, Zheng Y, Zhao M. Org. Chem. Front. 2019; 6: 506
- 6d Zeng M.-T, Wang M, Peng H.-Y, Cheng Y, Dong Z.-B. Synthesis 2018; 50: 644
- 6e Liu H, Jiang X. Chem. Asian J. 2013; 8: 2546
- 6f Li Y, Chen S, Wang M, Jiang X. Angew. Chem. Int. Ed. 2020; 59: 8907
- 6g Jiao J, Wang P, Xiao F, Zhang Z. Synlett 2022; 33: 569
- 7a Enders D, Rembiak A, Liebich JX. Synthesis 2011; 281
- 7b Poladura B, Martínez-Castañeda Á, Rodríguez-Solla H, Concellón C, del Amo V. Tetrahedron 2012; 68: 6438
- 8a Jiao J, Wei L, Ji X.-M, Hu M.-L, Tang R.-Y. Adv. Synth. Catal. 2016; 358: 268
- 8b Huang Z.-B, Xia X.-J, Huang Z.-H, Xu L, Zhang X.-Y, Tang R.-Y. Org. Biomol. Chem. 2020; 18: 1369
- 8c Song Z, Zhou Y, Zhang W, Zhan L, Yu Y, Chen Y, Jia W, Liu Z, Qian J, Zhang Y, Li C, Liang G. Eur. J. Med. Chem. 2019; 171: 54
- 8d Cheng C, Zhao M, Lai M, Zhai K, Shi B, Wang S, Luo R, Zhang L, Wu Z. Eur. J. Org. Chem. 2019; 2019: 2941
- 8e Zeng M.-T, Xu W, Liu X, Chang C.-Z, Zhu H, Dong Z.-B. Eur. J. Org. Chem. 2017; 2017: 6060
- 8f Xu W, Gao F, Dong Z.-B. Eur. J. Org. Chem. 2018; 2018: 821
- 8g Cao Q, Peng H.-Y, Cheng Y, Dong Z.-B. Synthesis 2018; 50: 1527
- 8h Cheng Y, Peng H.-Y, Dong Z.-B. Tetrahedron Lett. 2019; 60: 617
- 8i Dong Z.-B, Liu X, Bolm C. Org. Lett. 2017; 19: 5916
- 9a Wu Z, Lai M, Zhang S, Zhong X, Song H, Zhao M. Eur. J. Org. Chem. 2018; 2018: 7033
- 9b Peng H.-Y, Dong Z.-B. Eur. J. Org. Chem. 2019; 2019: 949
- 10a Li Q, Dong T, Liu X, Lei X. J. Am. Chem. Soc. 2013; 135: 4996
- 10b Shaikh AK, Cobb AJ. A, Varvounis G. Org. Lett. 2012; 14: 584
- 10c Sabarre A, Love J. Org. Lett. 2008; 10: 3941
- 11a Lavecchia A, Cosconati S, Limongelli V, Novellino E. ChemMedChem 2006; 1: 540
- 11b Johannesson P, Lindeberg G, Johansson A, Nikiforovich GV, Gogoll A, Synnergren B, Le Grèves M, Nyberg F, Karlén A, Hallberg A. J. Med. Chem. 2002; 45: 1767
- 12a Ramazanov I, Kadikova R, Zosim T, Dzhemilev U. Synthesis 2015; 47: 2670
- 12b Wu W, Dai W, Ji X, Cao S. Org. Lett. 2016; 18: 2918
- 12c Lin Y.-M, Lu G.-P, Cai C, Yi W.-B. Org. Lett. 2015; 17: 3310
- 12d Pan S, Li H, Huang Y, Xu X.-H, Qing F.-L. Org. Lett. 2017; 19: 3247
- 12e Kondoh A, Takami K, Yorimitsu H, Oshima K. J. Org. Chem. 2005; 70: 6468
- 12f Wang Z.-L, Tang R.-Y, Luo P.-S, Deng C.-L, Zhong P, Li J.-H. Tetrahedron 2008; 64: 10670
- 13a Huang Y, Ding J, Wu C, Zheng H, Weng Z. J. Org. Chem. 2015; 80: 2912
- 13b Velasco N, Virumbrales C, Sanz R, Suarez-Pantiga S, Fernandez-Rodriguez MA. Org. Lett. 2018; 20: 2848
- 13c Rueping M, Tolstoluzhsky N, Nikolaienko P. Chem. Eur. J. 2013; 19: 14043
- 13d Glenadel Q, Alazet S, Tlili A, Billard T. Chem. Eur. J. 2015; 21: 14694
- 13e Zhang C.-P, Vicic DA. Chem. Asian J. 2012; 7: 1756
- 14a Honeker R, Garza-Sanchez RA, Hopkinson MN, Glorius F. Chem. Eur. J. 2016; 22: 4395
- 14b Zhao Q, Poisson T, Pannecoucke X, Bouillon J.-P, Besset T. Org. Lett. 2017; 19: 5106
- 14c Liu S, Wang L, Ma Z, Zeng X, Xu B. Org. Chem. Front. 2020; 7: 3474
- 15a Zoghlami H, Chehidi I, Romdhani M, Chaabouni MM, Baklouti A. Tetrahedron Lett. 2007; 48: 5645
- 15b Wan J.-P, Zhong S, Xie L, Cao X, Liu Y, Wei L. Org. Lett. 2016; 18: 584
- 15c Zhang J, Wang E, Zhou Y, Zhang L, Chen M, Lin X. Org. Chem. Front. 2020; 7: 1490
- 16a Tu H.-Y, Hu B.-L, Deng C.-L, Zhang X.-G. Chem. Commun. 2015; 51: 15558
- 16b Liu Y.-R, Hu B.-L, Zhang X.-G. Chin. J. Chem. 2017; 35: 307
- 17 Fedorov OV, Scherbinina SI, Levin VV, Dilman AD. J. Org. Chem. 2019; 84: 11068