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Synthesis
DOI: 10.1055/a-2597-8248
DOI: 10.1055/a-2597-8248
paper
Metal-Free Synthesis of 1-(α-Hydroxyindole)-o-carboranes in Neat
This work was supported by the National Natural Science Foundation of China (22071201), Natural Science Foundation of Sichuan Science and Technology Program (2024NSFSC0028), and Mianyang Science and Technology Program (2023ZYDF008).
Abstract
An efficient and environmentally friendly protocol for the synthesis of 1-(α-hydroxyindole)-o-carboranes has been developed via Friedel–Crafts reaction of C3-H of indoles with 1-formyl-o-carborane in the absence of Lewis acid and solvent. The intermolecular σ-π interaction between indole and B–H bonds of o-carborane was proposed for promoting the Friedel–Crafts reaction of the C3-H of indole.
Key words
carborane - indole - Friedel–Crafts reaction - metal-free reaction - 1-(α-hydroxyindole)-o-carboraneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2597-8248.
- Supporting Information
Publication History
Received: 18 March 2025
Accepted after revision: 30 April 2025
Accepted Manuscript online:
30 April 2025
Article published online:
26 May 2025
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References
- 1a Poater J, Solà M, Viñas C, Teixidor F. Angew. Chem. Int. Ed. 2014; 53: 1219
- 1b Poater J, Viñas C, Bennour I, Escayola S, Sola M, Teixidor F. J. Am. Chem. Soc. 2020; 142: 9396
- 1c Poater J, Solà M, Viñas C, Teixidor F. Chem. Eur. J. 2016; 22: 7437
- 2a Hawthorne MF. Angew. Chem., Int. Ed. Engl. 1993; 32: 950
- 2b Lee W, Sarkar S, Ahn H, Kim JY, Lee YJ, Chang Y, Yoo J. Biochem. Bioph. Res. Commun. 2020; 522: 669
- 2c Hu K, Yang Z, Zhang L, Xie L, Wang L, Xu H, Josephson L, Liang SH, Zhang M.-R. Coord. Chem. Rev. 2020; 405: 213139
- 3a Dash BP, Satapathy R, Gaillard ER, Maguire JA, Hosmane NS. J. Am. Chem. Soc. 2010; 132: 6578
- 3b Wee K.-R, Cho Y.-J, Song JK, Kang SO. Angew. Chem., Int. Ed. 2013; 52: 968
- 3c Yang X, Jiang W, Knobler CB, Hawthorne MF. J. Am. Chem. Soc. 1992; 114: 9719
- 3d Oleshkevich E, Viñas C, Romero I, Choquesillo-Lazarte D, Haukka M, Teixidor F. Inorg. Chem. 2017; 56: 5502
- 4a Hosmane NS, Maguire JA. Comprehensive Organometallic Chemistry III, Vol. 3. Elsevier; Oxford: 2007: 175-264
- 4b Spokoyny AM, Machan CW, Clingerman DJ, Rosen MS, Wiester MJ, Kennedy RD, Stern CL, Sarjeant AA, Mirkin CA. Nat. Chem. 2011; 3: 590
- 4c Yao Z.-J, Jin G.-X. Coord. Chem. Rev. 2013; 257: 2522
- 4d Qiu Z, Ren S, Xie Z. Acc. Chem. Res. 2011; 44: 299
- 4e Fisher SP, Tomich AW, Lovera SO, Kleinsasser JF, Guo J, Asay MJ, Nelson HM, Lavallo V. Chem. Rev. 2019; 119: 8262
- 5a Prokhorov AM, Hofbeck T, Czerwieniec R, Suleymanova AF, Kozhevnikov DN, Yersin H. J. Am. Chem. Soc. 2014; 136: 9637
- 5b Kirlikovali KO, Axtell JC, Gonzalez A, Phung AC, Khan SI, Spokoyny AM. Chem. Sci. 2016; 7: 5132
- 5c Wu X, Guo J, Cao Y, Zhao J, Jia W, Chen Y, Jia D. Chem. Sci. 2018; 9: 5270
- 5d Koshino M, Tanaka T, Solin N, Suenaga K, Isobe H, Nakamura E. Science 2007; 316: 853
- 5e Núñez R, Romero I, Teixidor F, Viñas C. Chem. Soc. Rev. 2016; 45: 5147
- 5f Jiang Q, Wang Z, Wang G, Liu K, Xu W, Shang C, Gou X, Liu T, Fang YA. Chin. J. Chem. 2022; 40: 201
- 6a Issa F, Kassiou M, Rendina LM. Chem. Rev. 2011; 111: 5701
- 6b Scholz M, Hey-Hawkins E. Chem. Rev. 2011; 111: 7035
- 6c Ogawa T, Ohta K, Yoshimi T, Yamazaki H, Suzuki T, Ohta S, Endo Y. Bioorg. Med. Chem. Lett. 2006; 16: 3943
- 6d Ogawa T, Ohta K, Iijima T, Suzuki T, Ohta S, Endo Y. Bioorg. Med. Chem. 2009; 17: 1109
- 6e Ohta K, Ogawa T, Oda A, Kaise A, Endo Y. Bioorg. Med. Chem. Lett. 2015; 25: 4174
- 6f Ohta K, Ogawa T, Endo Y. Bioorg. Med. Chem. Lett. 2017; 27: 4030
- 7a Cao K, Zhang C.-Y, Xu T.-T, Wu J, Wen X.-Y, Jiang W.-J, Chen M, Yang J. Molecules 2020; 25: 391
- 7b Olid D, Núñez R, Viñas C, Teixidor F. Chem. Soc. Rev. 2013; 42: 3318
- 7c Dziedzic RM, Spokoyny AM. Chem. Commun. 2019; 55: 430
- 7d Quan Y, Xie Z. Chem. Soc. Rev. 2019; 48: 3660
- 7e Sivaev IB. Russ. J. Inorg. Chem. 2021; 66: 1289
- 7f Yu W.-B, Cui P.-F, Gao W.-X, Jin G.-X. Coord. Chem. Rev. 2017; 350: 300
- 7g Zhang X, Yan H. Coord. Chem. Rev. 2019; 378: 466
- 7h Cao K, Zhang C.-Y. Eur. J. Org. Chem. 2022; e202200737
- 7i Cao K, Zhang C.-Y, Wu J, Yang J. Handbook of CH-Functionalization . Wiley-VCH; Weinheim: 2023.
- 8a Kamal A, Qureshi AA. Tetrahedron 1963; 19: 513
- 8b Bader H, Oroshnik W. J. Am. Chem. Soc. 1959; 81: 163
- 8c Ke B, Qin Y, Wang Y, Wang F. Synth. Commun. 2005; 35: 1209
- 8d Bandgar BP, Shaikh KA. Tetrahedron Lett. 2003; 44: 1959
- 8e Shi X.-L, Xing X, Lin H, Zhang W. Adv. Synth. Catal. 2014; 356: 2349
- 8f Liang D, Huang W, Yuan L, Ma Y, Ma J, Ning D. Catal. Commun. 2014; 55: 11
- 8g Karam A, Alonso JC, Gerganova TI, Ferreira P, Bion N, Barrault J, Jerome F. Chem. Commun. 2009; 7000
- 9a Zeng X, Ji S, Yiwan S. Tetrahedron 2005; 61: 10235
- 9b Bandgar BP, Abasaheb VP, Kamble VT. ARKIVOC 2007; (xvi): 252
- 10a Zhou P, Li Y, Meagher KL, Richard GM, Harrison BL. Tetrahedron Lett. 2001; 42: 7333
- 10b Elayaraja R, Karunakaran RJ. Tetrahedron Lett. 2012; 53: 6901
- 11 Satapathy R, Dash BP, Zheng C, Maguire JA, Hosmane NS. J. Org. Chem. 2011; 76: 3562
- 12a Wu J, Cao K, Zhang C.-Y, Xu T.-T, Ding L.-F, Li B, Yang J. Org. Lett. 2019; 21: 5986
- 12b Cao K, Huang Y, Yang J, Wu J. Chem. Commun. 2015; 51: 7257
- 12c Zhang C.-Y, Cao K, Xu T.-T, Wu J, Jiang L, Yang J. Chem. Commun. 2019; 55: 830
- 12d Cao K, Xu T.-T, Wu J, Jiang L, Yang J. Chem. Commun. 2016; 52: 11446
- 12e Wu J, Cao K, Zhang C.-Y, Xu T.-T, Wen X.-Y, Li B, Yang J. Inorg. Chem. 2020; 59: 17340
- 12f Xu T.-T, Cao K, Wu J, Zhang C.-Y, Yang J. Inorg. Chem. 2018; 57: 2925
- 12g Xu T.-T, Cao K, Zhang C.-Y, Wu J, Jiang L, Yang J. Chem. Commun. 2018; 54: 13603
- 12h Cao K, Xu T.-T, Wu J, Zhang C.-Y, Wen X.-Y, Yang J. Inorg. Chem. 2021; 60: 1080
- 12i Xu T.-T, Cao K, Zhang C.-Y, Wu J, Ding L.-F, Yang J. Org. Lett. 2019; 21: 9276
- 12j Zhang C.-Y, Cao K, Yang H.-B, Ding L.-F, Yang J. J. Org. Chem. 2022; 87: 10928
- 12k Zhang C.-Y, Cao K, Liu D, Yang H.-B, Teng C.-C, Li B, Yang J. Dalton Trans. 2023; 52: 2933
- 13 CCDC 2193713 (7a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
- 14 Zhang X, Dai H, Yan H, Zou W, Cremer D. J. Am. Chem. Soc. 2016; 138: 4334
- 15 Dozzo P, Kasar RA, Kahl SB. Inorg. Chem. 2005; 44: 8053
Selected references for applications in BNCT:
Selected references for applications in supramolecular design/nanomaterials:
Selected references for applications in coordination/organometallic chemistry:
Selected references for applications in optoelectronic functional materials:
Selected reviews for selective functionalization of o-carboranes:
Selected references for the synthesis of bis(indolyl)alkanes: