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Synthesis 2025; 57(06): 1223-1229
DOI: 10.1055/a-2502-7704
DOI: 10.1055/a-2502-7704
paper
Scandium(III)-Catalyzed N-Alkylation of Carbazoles with Alcohols
This research was supported by Zhejiang Provincial Natural Science Foundation of China (Grant No. LY23B040001) and Programs Supported by Ningbo Natural Science Foundation (Grant No. 202003N4009).

Abstract
A general and efficient protocol has been developed for the N-alkylation of carbazoles with benzylic alcohols via scandium-catalyzed reaction. This transformation proceeds smoothly under an air atmosphere and features simple reaction conditions and wide substrate scope, which deliver a variety of N-alkylated carbazoles with up to 99% yields and broad functional group compatibilities.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2502-7704.
- Supporting Information
Publication History
Received: 09 October 2024
Accepted after revision: 15 December 2024
Accepted Manuscript online:
15 December 2024
Article published online:
22 January 2025
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References
- 1a Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
- 1b Schmidt AW, Reddy KR, Knolker HJ. Chem. Rev. 2012; 112: 3193
- 1c Bashir M, Bano A, Ijaz AS, Chaudhary BA. Molecules 2015; 20: 13496
- 1d Kumar N, Lal N, Nemaysh V, Luthra PM. Bioorg. Chem. 2020; 100: 103911
- 1e Wang GQ, Sun SF, Guo H. Eur. J. Med. Chem. 2022; 229: 113999
- 2a Zhang Y, Tangadanchu VK. R, Cheng Y, Yang RG, Lin JM, Zhou CH. ACS Med. Chem. Lett. 2018; 9: 244
- 2b Xiong Y, Zhang GZ. Org. Lett. 2019; 21: 7873
- 2c Xiao E.-K, Wu X.-T, Ma F, Feng X, Chen P, Jiang Y.-J. Org. Lett. 2020; 23: 449
- 2d Sun HL, Yang F, Ye WT, Wang JJ, Zhu R. ACS Catal. 2020; 10: 4983
- 3a Kaarsholm NC, Madsen P, Schlein M, Olsen HB, Havelund S, Steensgaard DB, Ludvigsen S, Jakobsen P, Petersen AK, Schluckebier G. Patent WO2004056347 A2, 2004
- 3b Poss MA, Tortolani DR, Dodd DS, Mussari CP, Tokarski JS, Gavai AV, Zhao YF, Delucca GV, O’Malley D, Norris DJ, Gill P, Quesnelle CA, Han WC. Patent US20140256700 A1, 2014
- 3c Ten Brink RE, Merchant KM, McCarthy TJ. Patent WO2003089438 A1, 2003
- 4 Kumar R, Van der Eycken EV. Chem. Soc. Rev. 2013; 42: 1121
- 5a Guillena G, Ramón DJ, Yus M. Chem. Rev. 2009; 110: 1611
- 5b Bähn S, Imm S, Mevius K, Neubert L, Tillack A, Williams JM. J, Beller M. Chem. Eur. J. 2010; 16: 3590
- 5c Chen M, Sun J. Angew. Chem. Int. Ed. 2017; 56: 4583
- 5d Zhang LY, Wu BQ, Chen ZT, Hu JJ, Zeng XF, Zhong GF. Chem. Commun. 2018; 54: 9230
- 5e Chang CY, Lin YH, Wu YK. Chem. Commun. 2019; 55: 1116
- 5f Mouhsine B, Karim A, Dumont C, Saint Pol A, Suisse I, Sauthier M. Eur. J. Org. Chem. 2022; 13
- 6a Kobayashi S. Eur. J. Org. Chem. 1999; 15
- 6b Kobayashi S, Sugiura M, Kitagawa H, Lam WW. L. Chem. Rev. 2002; 102: 2227
- 6c Pellissier H. Coord. Chem. Rev. 2016; 313: 1
- 6d Banerjee B. ARKIVOC 2017; (i): 1
- 6e Wu Y.-H, Zhang L.-Y, Wang N.-X, Xing Y. Catal. Rev. 2020; 64: 679
- 6f Sun D, Xu J, Liu G, Chen Y.-H. Eur. J. Org. Chem. 2024; e202400540
- 7a Wu XT, Xiao EK, Ma F, Yin J, Wang J, Chen P, Jiang YJ. J. Org. Chem. 2021; 86: 6734
- 7b Xiao EK, Wu XT, Ma F, Miao LW, Jiang YJ, Chen P. Chem. Commun. 2021; 57: 7148
- 7c Yin J, Chen P, Miao LW, Wang J, Jiang YJ. Eur. J. Org. Chem. 2023; e202300290
- 7d Ma F, Wu XT, Miao LW, Sun F, Jiang YJ, Chen P. Adv. Synth. Catal. 2022; 364: 3477
- 7e Li MY, Chen P, Pan MX, Hu HL, Jiang YJ. Org. Biomol. Chem. 2024; 22: 6090