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(17): 2702-2712
DOI: 10.1055/a-2096-7045
DOI: 10.1055/a-2096-7045
paper
A Nickel(II) Chloride and Tetrahydroxydiboron Cocatalyzed Facile Synthesis of Benzo[b]azepines with an Appended Fluorinated Side Chain
The authors are grateful for the financial support from the National Natural Science Foundation of China (No. 22271214).
Abstract
A novel nickel-catalyzed chemoselective cascade reaction strategy towards the synthesis of benzo[b]azepines was developed. The method is characterized by simple and mild conditions, low cost, and a wide range of substrates. This method enabled the facile and efficient synthesis of a series of 2,3,4,5-tetrahydro-1H-benzo[b]azepine analogues with an appended fluorinated side chain.
Key words
tetrahydroxydiboron - ethyl bromodifluoroacetate - nickel catalyst - radical cascade - benzo[b]azepinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2096-7045.
- Supporting Information
Publikationsverlauf
Eingereicht: 19. April 2023
Angenommen nach Revision: 22. Mai 2023
Accepted Manuscript online:
22. Mai 2023
Artikel online veröffentlicht:
19. Juni 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Puig-Antich J, Perel JM, Lupatkin W, Chambers WJ, Tabrizi MA, King J, Goetz R, Davies M, Stiller RL. Arch. Gen. Psychiatry 1987; 44: 81
- 2 Sallee FR, Pollock BG. Clin. Pharmacokinet. 1990; 18: 346
- 3 Yamamoto Y, Ishihara Y, Kuntz ID. J. Med. Chem. 1994; 37: 3141
- 4 Jiang Y.-R, Yang Y.-Y, Chen Y.-L, Liang Z.-J. Curr. Comput.-Aided Drug Des. 2013; 9: 385
- 5 Yempala T, Babu T, Gibson D, Cassels BK. Synth. Commun. 2019; 50: 438
- 6 Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
- 7 Heidelberger C, Chaudhuri NK, Danneberg P, Mooren D, Griesbach L, Duschinsky R, Schnitzer RJ. Nature 1957; 179: 663
- 8 Wong DT, Horng JS, Bymaster FP, Hauser KL, Molloy BB. Life Sci. 1974; 15: 471
- 9 Robertson JF. R, Come SE, Jones SE, Beex L, Kaufmann M, Makris A, Nortier JW. R, Possinger K, Rutqvist L.-E. Eur. J. Cancer 2005; 41: 346
- 10 Carvalho MF, Oliveira RS. Crit. Rev. Biotechnol. 2017; 37: 880
- 11 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 12 Zhou Y, Wang J, Gu Z, Wang S, Zhu W, Acena JL, Soloshonok VA, Izawa K, Liu H. Chem. Rev. 2016; 116: 422
- 13 Hassner A, D’Costa R, McPhail AT, Butler W. Tetrahedron Lett. 1981; 22: 3691
- 14 Chen W.-Y, Gilman NW. J. Heterocycl. Chem. 1983; 20: 663
- 15 Scheiner P. J. Org. Chem. 1967; 32: 2628
- 16 Tamura SY, Goldman EA, Bergum PW, Semple JE. Bioorg. Med. Chem. Lett. 1999; 9: 2573
- 17 Li D, Park Y, Yang J. Org. Lett. 2018; 20: 7526
- 18 Clark AJ, Jones K, McCarthy C, Storey JM. D. Tetrahedron Lett. 1991; 32: 2829
- 19 Qadir M, Cobb J, Sheldrake PW, Whittall N, White AJ. P, Hii KK, Horton PN, Hursthouse MB. J. Org. Chem. 2005; 70: 1545
- 20 Qadir M, Priestley RE, Rising TW. D. F, Gelbrich T, Coles SJ, Hursthouse MB, Sheldrake PW, Whittall N, Hii KK. Tetrahedron Lett. 2003; 44: 3675
- 21 Suh CW, Kwon SJ, Kim DY. Org. Lett. 2017; 19: 1334
- 22 Waldmann H, Eberhardt L, Wittstein K, Kumar K. Chem. Commun. 2010; 46: 4622
- 23 Wang R, Jin R.-X, Qin Z.-Y, Bian K.-J, Wang X.-S. Chem. Commun. 2017; 53: 12229
- 24 Hu J, Pu T.-J, Xu Z.-W, Xu W.-Y, Feng Y.-S. Adv. Synth. Catal. 2019; 361: 708
- 25 Liu L, Aguilera MC, Lee W, Youshaw CR, Neidig ML, Gutierrez O. Science 2021; 374: 432
- 26 Li C, Xue L, Zhou J, Zhao Y, Han G, Hou J, Song Y, Liu Y. Org. Lett. 2020; 22: 3291
- 27 Meng Z, Zhang X, Shi M. Org. Chem. Front. 2021; 8: 3796
- 28 Qu C, Xu P, Ma W, Cheng Y, Zhu C. Chem. Commun. 2015; 51: 13508
- 29 Xiao Q, Lu M, Deng Y, Jian J.-X, Tong Q.-X, Zhong J.-J. Org. Lett. 2021; 23: 9303
- 30 Zhuang X, Shi X, Zhu R, Sun B, Su W, Jin C. Org. Chem. Front. 2021; 8: 736
- 31 Zheng J, Chen P, Yuan Y, Cheng J. J. Org. Chem. 2017; 82: 5790
- 32 Chen H, Wang X, Guo M, Zhao W, Tang X, Wang G. Org. Chem. Front. 2017; 4: 2403
- 33 Wang X, Li M, Yang Y, Guo M, Tang X, Wang G. Adv. Synth. Catal. 2018; 360: 2151
- 34 Wang X, Liu J, Yu Z, Guo M, Tang X, Wang G. Org. Lett. 2018; 20: 6516
- 35 Yang Y, Yuan F, Ren X, Wang G, Zhao W, Tang X, Guo M. J. Org. Chem. 2019; 84: 4507
- 36 Yuan F, Zhou S, Yang Y, Guo M, Tang X, Wang G. Org. Chem. Front. 2018; 5: 3306
- 37 Sun Z.-Y, Zhou S, Yang K, Guo M, Zhao W, Tang X, Wang G. Org. Lett. 2020; 22: 6214
- 38 Yang Z, Chen L, Sun Q, Guo M, Wang G, Zhao W, Tang X. J. Org. Chem. 2022; 87: 3788
- 39 Leishner T, Suarez LA, Spannenberg A, Junge K, Nova A, Beller M. Chem. Sci. 2019; 10: 10566
- 40 Cerichelli G, Luchetti L. Tetrahedron 1993; 49: 10733
- 41 Perumal G, Kandasamy M, Ganesan B, Govindan K, Sathya H, Hung M.-Y, Senadi GC, Wu Y.-C, Lin W.-Y. Tetrahedron 2021; 80: 131891
- 42 Zhao Y, Ge S. Angew. Chem. Int. Ed. 2022; 61: e202116133
- 43 Fujita T, Morioka R, Arita T, Ichikawa J. Chem. Commun. 2018; 54: 12938
- 44 Xu P, Wang G, Zhu Y, Li W, Cheng Y, Li S, Zhu C. Angew. Chem. Int. Ed. 2016; 55: 2939