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 2023; 55(18): 3040-3046
DOI: 10.1055/a-2025-1822
DOI: 10.1055/a-2025-1822
paper
Special Issue Electrochemical Organic Synthesis
Electrochemical Difunctionalization of Alkenes towards the Synthesis of β-Bromoethers under Metal-Free Conditions
Financial supported by National Natural Science Foundation of China (NSFC) (22161028, 21861026 and 22075123) and Jiangxi Provincial Natural Science Foundation (20224BAB203012) is gratefully acknowledged.
Abstract
A metal-free electrochemical method for vicinal difunctionalization of various alkenes with dibromomethane in alcohol as solvent has been well established to synthesize the corresponding β-bromo-α-alkyloxyalkanes with good functional group tolerance under ambient conditions. Preliminary mechanistic studies indicate the oxidation of bromine source occurs prior to that of alkene substrate with the involvement of bromine radical during electrolysis.
Key words
difunctionalization - alkene - β-bromoethers - electrochemical transformation - metal-free conditionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2025-1822.
- Supporting Information
Publikationsverlauf
Eingereicht: 16. Dezember 2022
Angenommen nach Revision: 02. Februar 2023
Accepted Manuscript online:
02. Februar 2023
Artikel online veröffentlicht:
09. März 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Lecourt C, Allievi L, Sanogo Y, Zeghbib N, Othman RB, Lannou MI, Sorin G, Ardisson J. Nat. Prod. Rep. 2018; 35: 105
- 2a Li Z, Fang G, Gu Q, Liu X. Chem. Soc. Rev. 2020; 49: 32
- 2b Lan X, Wang N, Xing Y. Eur. J. Org. Chem. 2017; 5821
- 2c Yin G, Mu X, Liu G. Acc. Chem. Res. 2016; 49: 2413
- 3a Patil DV, Si T, Kim HY, Oh K. Org. Lett. 2021; 23: 3105
- 3b Tao Z, Gilbert BB, Denmark SE. J. Am. Chem. Soc. 2019; 141: 19161
- 4a Xue Q, Xie J, Xu P, Hu K, Cheng Y, Zhu C. ACS Catal. 2013; 3: 1365
- 4b Haro T, Nevado C. Angew. Chem. Int. Ed. 2011; 50: 906
- 4c Mumford EM, Hemric BN, Denmark SE. J. Am. Chem. Soc. 2021; 143: 13408
- 4d Zhu H, Chen P, Liu G. J. Am. Chem. Soc. 2014; 136: 1766
- 4e Lai S, Wei B, Wang J, Yu W, Han B. Angew. Chem. Int. Ed. 2021; 60: 21997
- 5a Li N, Chang R, Yang W, Zhang Z, Guo Z. Organometallics 2020; 39: 2057
- 5b Zhou M, Song R, Ouyang X, Liu Y, Wei W, Deng G, Li J. Chem. Sci. 2013; 4: 2690
- 5c Zheng L, Huang H, Yang C, Xia W. Org. Lett. 2015; 17: 1034
- 5d Wang H, Guo L, Duan X. Adv. Synth. Catal. 2013; 355: 2222
- 5e Wei W, Zhou M, Fan J, Liu W, Song R, Liu Y, Hu M, Xie P, Li J. Angew. Chem. Int. Ed. 2013; 52: 3638
- 5f Mu X, Wu T, Wang H, Guo Y, Liu G. J. Am. Chem. Soc. 2012; 134: 878
- 5g Wang X, Li Y, Liu H, Zhang B, Gou X, Wang Q, Ma J, Liang Y. J. Am. Chem. Soc. 2019; 141: 13914
- 6a Liu Y, Yang X, Song R, Luo S, Li J. Nat. Commun. 2017; 8: 14720
- 6b Cheng X, Zhang Y, Wang J, Gu Q, Li Z, Liu X. J. Am. Chem. Soc. 2022; 144: 18081
- 6c Jiang H, Studer A. Chem. Soc. Rev. 2020; 49: 1790
- 6d Chen C, Chen P, Liu G. J. Am. Chem. Soc. 2015; 137: 15648
- 7a Zhang L, Liu S, Zhao Z, Su H, Hao J, Wang Y. Chem. Sci. 2018; 9: 6085
- 7b Liu H, Guo Q, Chen C, Wang M, Xu Z. Org. Chem. Front. 2018; 5: 1522
- 7c Geng X, Lin F, Wang X, Jiao N. Org. Lett. 2017; 19: 4738
- 7d Su Y, Liu G, Liu J, Tram L, Qiu H, Doyle MP. J. Am. Chem. Soc. 2020; 142: 13846
- 9a Jalali M, Hyland CJ. T, Bissember AC, Yates BF, Ariafard A. ACS Catal. 2021; 11: 5795
- 9b Yamauchi D, Nishimura T, Yorimitsu H. Angew. Chem. Int. Ed. 2017; 56: 7200
- 9c Li X, Fu B, Zhang Q, Yuan X, Zhang Q, Xiong T, Zhang Q. Angew. Chem. Int. Ed. 2020; 59: 23056
- 9d Wang D, Dong B, Wang Y, Qian J, Zhu J, Zhao Y, Shi Z. Nat. Commun. 2019; 10: 3539
- 10a Kumar R, Jain VK, Jain N. J. Org. Chem. 2022; 87: 11939
- 10b Zhang S, Wang C, Ye X, Shi X. Angew. Chem. Int. Ed. 2020; 59: 20470
- 10c Feng G, Sun S, Liu G, Long H, Liu L. Org. Lett. 2018; 20: 7522
- 11 Zhang P, Zhang L, Li J, Shoberu A, Zou J, Zhang W. Org. Lett. 2017; 19: 5537
- 12a Prieto A, Diter P, Toffano M, Hannedouche J, Magnier E. Adv. Synth. Catal. 2019; 361: 436
- 12b Zhang D, Wang H, Bolm C. Chem. Commun. 2018; 54: 5772
- 13 Liu C, Zhu M, Wei W, Yang D, Cui H, Liu X, Wang H. Org. Chem. Front. 2015; 2: 1356
- 14a Weber S, Zobernig D, Stöger B, Veiros LF, Kirchner K. Angew. Chem. Int. Ed. 2021; 60: 24488
- 14b Zhong M, Gagné Y, Hope TO, Pannecoucke X, Frenette M, Jubault P, Poisson T. Angew. Chem. Int. Ed. 2021; 60: 14498
- 14c Ulm F, Cornaton Y, Djukic JP, Chetcuti MJ, Ritleng V. Chem. Eur. J. 2020; 26: 8916
- 15a Bag R, Sar D, Punniyamurthy T. ACS Omega 2017; 2: 6278
- 15b Giglio BC, Schmidt VA, Alexanian EJ. J. Am. Chem. Soc. 2011; 133: 13320
- 16a Yang D, Huang B, Wei W, Li J, Lin G, Liu Y, Ding J, Sun P, Wang H. Green Chem. 2016; 18: 5630
- 16b Liu Q, Liu F, Yue H, Zhao X, Li J, Wei W. Adv. Synth. Catal. 2019; 361: 5277
- 17 Egami H, Yoneda T, Uku M, Ide T, Kawato Y, Hamashima Y. J. Org. Chem. 2016; 81: 4020
- 18a Wei W, Ji J. Angew. Chem. Int. Ed. 2011; 50: 9097
- 18b Bakhtiary A, Heravi MR. P, Hassanpour A, Amini I, Vessally E. RSC Adv. 2021; 11: 470
- 19a Meyer TH, Choi I, Tian C, Ackermann L. Chem 2020; 6: 1
- 19b Cheng X, Lei A, Mei T, Xu H, Xu K, Zeng C. CCS Chem. 2022; 4: 1120
- 19c Wang Z, Ma C, Fang P, Xu H, Mei T. Acta Chim. Sinica 2022; 80: 1115
- 19d Yuan Y, Yang J, Lei A. Chem. Soc. Rev. 2021; 50: 10058
- 19e Novaes LF. T, Liu J, Shen Y, Lu L, Meinhardt JM, Lin S. Chem. Soc. Rev. 2021; 50: 7941
- 20a Thadathil DA, Varghese A, Radhakrishnan KV. Asian J. Org. Chem. 2021; 10: 2820
- 20b Mei H, Yin Z, Liu J, Sun H, Han J. Chin. J. Chem. 2019; 37: 292
- 20c Sauer GS, Lin S. ACS Catal. 2018; 8: 5175
- 20d Thadathil DA, Varghese A, Radhakrishnan KV. Asian J. Org. Chem. 2021; 10: 2820
- 20e Martins GM, Shirinfar B, Hardwick T, Ahmed N. ChemElectroChem 2019; 6: 1300
- 20f Sauer GS, Lin S. ACS Catal. 2018; 8: 5175
- 21 Cai C, Shu X, Xu H. Nat. Commun. 2019; 10: 1
- 22 Xu F, Zhu L, Zhu S, Yan X, Xu H. Chem. Eur. J. 2014; 20: 12740
- 23a Huang Y, Hong H, Zou Z, Liao C, Lu J, Qin Y, Li Y, Lu C. Org. Biomol. Chem. 2019; 17: 5014
- 23b Zhang L, Zhang G, Wang P, Li Y, Lei A. Org. Lett. 2018; 20: 7396
- 24 Zou Z, Zhang W, Wang Y, Kong L, Karitsis G, Wang Y, Pan Y. Org. Lett. 2019; 21: 1857
- 25 Xiong P, Long H, Song J, Wang Y, Li J, Xu H. J. Am. Chem. Soc. 2018; 140: 16387
- 26 Meng X, Zhong P, Wang Y, Wang H, Tang H, Pan Y. Adv. Synth. Catal. 2020; 362: 506
- 27 Wan C, Song R, Li J. Org. Lett. 2019; 21: 2800
- 28 Zhou P, Niu K, Song H, Liu Y, Wang Q. Green Chem. 2022; 24: 5760
- 29 Zhang Y, Zhao X, Bi C, Lu W, Song M, Wang D, Qing G. Green Chem. 2021; 23: 1691
- 30 Dai C, Shen Y, Wei Y, Liu P, Sun P. J. Org. Chem. 2021; 86: 13711
- 31a Ye Z, Zhu R, Wang F, Jiang H, Zhang F. Org. Lett. 2021; 23: 8240
- 31b Siu JC, Sauer GS, Saha A, Macey RL, Fu N, Chauviré T, Lancaster KM, Lin S. J. Am. Chem. Soc. 2018; 140: 12511
- 31c Zhu Y, Jiang C, Li H, Liu P, Sun P. J. Org. Chem. 2022; 87: 11031
- 32 Yang J, Sun X, Yan K, Sun H, Sun S, Jia X, Zhang F, Wen J. Adv. Synth. Catal. 2022; 364: 2735
- 33a Chen J, Mei L, Wang H, Hu L, Sun X, Shi J, Li Q. ChemistryOpen 2019; 8: 1230
- 33b Meng X, Zhong P, Wang Y, Wang H, Tang H, Pan Y. Adv. Synth. Catal. 2020; 362: 506
- 34a Yuan Y, Chen Y, Tang S, Huang Z, Lei A. Sci. Adv. 2018; 4: 5312
- 34b Wang Y, Deng L, Mei H, Du B, Han J, Pan Y. Green Chem. 2018; 20: 3444
- 35a Zhang C, Yang M, Qiu Y, Song M, Wang H, Yang M, Xie W, Wu J, Ye S. Chem. Sci. 2022; 13: 11785
- 35b Liu J, Xu J, Mei H, Han J. Green Chem. 2022; 24: 6113
- 35c Ye Z, Gao J, Duan X, Guan J, Liu F, Chen K, Xiao J, Xiang H, Yang H. Chem. Commun. 2021; 57: 8969
- 35d Kong X, Yu K, Chen Q, Xu B. Asian J. Org. Chem. 2020; 9: 1
- 35e Zhang Z, Yan J, Ma D, Sun J. Chin. Chem. Lett. 2019; 30: 1509
- 36a Ullmann’s Encyclopedia of Industrial Chemistry, 6th ed., Electronic Release. Wiley-VCH; Weinheim: 1998
- 36b Cabanal-Duvillard I, Berrier JF, Royer J, Husson HP. Tetrahedron Lett. 1998; 39: 5181
- 37 Bityukov OV, Vil VA, Nikishin GI, Terent’ev AO. Adv. Synth. Catal. 2021; 363: 3070
- 38 Seitz J, Wirth T. Org. Biomol. Chem. 2021; 19: 6892
- 39a Fu Z, Hao G, Fu Y, He D, Xun T, Guo S, Cai H. Org. Chem. Front. 2020; 7: 590
- 39b He D, Yao J, Ma B, Wei J, Hao G, Tuo X, Guo S, Fu Z, Cai H. Green Chem. 2020; 22: 1559
- 39c Fu Z, Ying J, He D, Yi X, Guo S, Cai H. Green Chem. 2022; 24: 130
- 39d Fu Z, Yi X, Fang Z, Zhong T, He D, Guo S, Cai H. Chem Asian J. 2022; 17: e202200780
- 40 Lin X, Zeng C, Liu C, Fang Z, Guo K. Org. Biomol. Chem. 2021; 19: 1352
- 41a Sun X, Ma H, Mei T, Fang P, Hu Y. Org. Lett. 2019; 21: 3167
- 41b Gao M, Zhou K, Xu B. Adv. Synth. Catal. 2019; 361: 1
- 42 Zhang T.-T, Luo M.-J, Li Y, Song R.-J, Li J.-H. Org. Lett. 2020; 22: 7250
- 43 Bai Y, Li Y, Zhang Z, Yang X, Zhang Z, Chen L, Li Y, Zeng X, Zhang M. Tetrahedron Lett. 2022; 101: 153923