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 2020; 52(05): 711-718
DOI: 10.1055/s-0039-1691486
DOI: 10.1055/s-0039-1691486
paper
Electrochemically Induced Thiocyanation of Enaminones: Synthesis of Functionalized Alkenes and Chromones
This work was supported by the Natural Science Foundation of Hunan Province (No. 2019JJ50214), and the Joint Funds of Hunan Province Engineering Research Center of Radioactive Control Technology in Uranium Mining and Metallurgy & Hunan Province Engineering Technology Research Center of Uranium Tailings Treatment Technology (2019YKZX2012).Weitere Informationen
Publikationsverlauf
Received: 16. September 2019
Accepted after revision: 29. Oktober 2019
Publikationsdatum:
14. November 2019 (online)
Abstract
A simple and efficient electrochemically induced thiocyanation of enaminones under undivided electrolytic conditions has been developed. With this protocol, various polyfunctionalized alkenes and chromones could be obtained in good to excellent yields using readily available KSCN as the thiocyanation reagent under catalyst-, oxidant-, and transition-metal-free conditions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691486.
- Supporting Information
-
References
- 1a Dean LJ, Prinsep MR. Nat. Prod. Rep. 2017; 34: 1359
- 1b Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
- 1c Edrada RA, Wray V, Proksch P. J. Nat. Prod. 2003; 66: 1512
- 1d Houmam A, Hamed EM, Still IW. J. Am. Chem. Soc. 2003; 125: 7258
- 1e Elhalem E, Bailey BN, Docampo R, Ujváry I, Szajnman SH, Rodriguez JB. J. Med. Chem. 2002; 45: 3984
- 2 Brown SP, Smith AB. III. J. Am. Chem. Soc. 2015; 137: 4034
- 3a Lu X, Wang H, Gao R, Sun D, Bi X. RSC Adv. 2014; 4: 28794
- 3b Billard T, Langlois BR, Medebielle M. Tetrahedron Lett. 2001; 42: 3463
- 4 Bayarmagnai B, Matheis C, Jouvin K, Goossen LJ. Angew. Chem. Int. Ed. 2015; 54: 5753
- 5 Renard PY, Schwebel H, Varyron P, Josien L, Valleix A, Mioskowski C. Chem. Eur. J. 2002; 8: 2910
- 6a Chen B, Guo S, Guo X, Zhang G, Yu Y. Org. Lett. 2015; 17: 4698
- 6b Falck JR, Gao S, Prasad RN, Koduru SR. Bioorg. Med. Chem. Lett. 2008; 18: 1768
- 7a Fan W, Yang Q, Xu F, Li P. J. Org. Chem. 2014; 79: 10588
- 7b Samanta S, Chatterjee R, Santra S, Hajra A, Khalymbadzha LA, Zyryanov GV, Majee A. ACS Omega 2018; 3: 13081
- 7c Dey A, Hajra A. Adv. Synth. Catal. 2019; 361: 842
- 7d Lu LH, Zhou SJ, He WB, Xia W, Chen P, Yu X, Xu X, He WM. Org. Biomol. Chem. 2018; 16: 9064
- 7e Jiang G, Zhu C, Li J, Wu W, Jiang HF. Adv. Synth. Catal. 2017; 359: 1208
- 7f Chen J, Wang T, Wang T, Lin A, Yao H, Xu J. Org. Chem. Front. 2017; 4: 130
- 7g Yang SM, He TJ, Lin DZ, Huang JM. Org. Lett. 2019; 21: 1958
- 7h Hoque IU, Chowdhury SR, Maity SP. J. Org. Chem. 2019; 84: 3025
- 7i Ye A.-H, Zhang Y, Xie Y.-Y, Luo H.-Y, Dong J.-W, Liu X.-D, Song X.-F, Ding T, Chen Z.-M. Org. Lett. 2019; 21: 5106
- 7j Wu D, Qiu J, Karmaker PG, Yin H, Chen F.-X. J. Org. Chem. 2018; 83: 1576
- 7k Li C, Long P, Wu H, Yin H, Chen F.-X. Org. Biomol. Chem. 2019; 17: 7131
- 8a Liang Z, Wang F, Chen P, Liu G. Org. Lett. 2015; 17: 2438
- 8b Zhu N, Wang F, Chen P, Ye J, Liu G. Org. Lett. 2015; 17: 3580
- 8c Laali KK, Nandi GC, Bunge SD. Tetrahedron Lett. 2014; 55: 2401
- 9 Chen Q, Lei Y, Wang Y, Wang C, Wang Y, Xu Z, Wang H, Wang R. Org. Chem. Front. 2017; 4: 369
- 10a Guo Y, Liu Y, Wan JP. J. Org. Chem. 2019; 84: 2243
- 10b Zhang XZ, Ge DL, Chen SY, Yu XQ. RSC Adv. 2016; 6: 66320
- 11a Wang QQ, Xu K, Jiang YY, Liu YG, Sun BG, Zeng CC. Org. Lett. 2017; 19: 5517
- 11b Fu N, Li L, Yang Q, Luo S. Org. Lett. 2017; 19: 2122
- 11c Wu ZJ, Xu HC. Angew. Chem. Int. Ed. 2017; 56: 4734
- 12a Li WC, Zeng CC, Hu LM, Tian HYu, Little RD. Adv. Synth. Catal. 2013; 355: 2884
- 12b Yang YZ, Song RJ, Li JH. Org. Lett. 2019; 21: 3228
- 12c Kang LS, Luo MH, Lam CM, Hu LM, Little RD, Zeng CC. Green Chem. 2016; 18: 3767
- 12d Koleda O, Broese T, Noetzel J, Roemelt M, Suna E, Francke R. J. Org. Chem. 2017; 82: 11669
- 12e Gieshoff T, Kehl A, Schollmeyer D, Moeller KD, Waldvogel SR. Chem. Commun. 2017; 53: 2974
- 12f Hayrapetyan D, Shkepu V, Seilkhanov OT, Zhanabil Z, Lam K. Chem. Commun. 2017; 53: 8451
- 12g Jiang YY, Liang S, Zeng CC, Hu LM, Sun BG. Green Chem. 2016; 18: 6311
- 12h Jiang YY, Wang QQ, Liang S, Hu LM, Lieelt RD, Zeng CC. J. Org. Chem. 2016; 81: 4713
- 12i Wang Y, Qian P, Su JH, Li Y, Bi M, Zha Z, Wang Z. Green Chem. 2017; 19: 4769
- 12j Zhao HB, Liu ZJ, Song J, Xu HC. Angew. Chem. Int. Ed. 2017; 56: 12732
- 12k Li C, Kawamata Y, Nakamura H, Vantourout JC, Liu Z, Hou Q, Bao D, Starr JT, Chen J, Yan M, Baran PS. Angew. Chem. Int. Ed. 2017; 56: 13088
- 12l Huang P, Wang P, Tang S, Fu Z, Lei A. Angew. Chem. Int. Ed. 2018; 57: 8115
- 12m Niu L, Wang S, Liu J, Yi H, Liang XA, Liu T, Lei A. Chem. Commun. 2018; 54: 1659
- 12n Mo SK, Teng QH, Pan YM, Tang HT. Adv. Synth. Catal. 2019; 361: 1756
- 12o Wan C, Song RJ, Li JH. Org. Lett. 2019; 21: 2800
- 12p Wen J, Zhang L, Yang X, Niu C, Wang S, Wei W, Sun X, Yang J, Wang H. Green Chem. 2019; 21: 3597
- 13a Yu Q, Zhang Y, Wan J.-P. Green Chem. 2019; 21: 3436
- 13b Wan JP, Tu Z, Wang Y. Chem. Eur. J. 2019; 25: 6907
- 13c Guo Y, Wang G, Wei L, Wan J.-P. J. Org. Chem. 2019; 84: 2984
- 13d Yang L, Wei L, Wan JP. Chem. Commun. 2018; 54: 7475
- 13e Sun J, Cheng X, Mansaray JK, Fei W, Wan J, Yao W. Chem. Commun. 2018; 54: 13953
- 13f Zhou P, Hu B, Li L, Rao K, Yang J, Fu C. J. Org. Chem. 2017; 82: 13268
- 13g Xu H, Zhou B, Zhou P, Zhou J, Shen Y, Yu F.-C, Lu L.-L. Chem. Commun. 2016; 52: 8002
- 13h Yang Z, Hu L, Cao T, An L, Li L.-J, Yang T, Zhou C. New J. Chem. 2019; 43: 16441
- 13i Yang Z, Liu S, Li A, Liao J, Li L, Yang T, Zhou C. ChemistrySelect 2019; 4: 6583
- 13j Fu L, Wan J.-P. Asian J. Org. Chem. 2019; 8: 767
- 13k Xaing H, Zhao Q, Tang Z, Xiao J, Xia P, Wang C, Yang C, Chen X, Yang H. Org. Lett. 2017; 19: 146
- 14 Dyga M, Hayrapetyan D, Rit RK, Gooßen LJ. Adv. Synth. Catal. 2019; 361: 3548