Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2021; 53(20): 3815-3826
DOI: 10.1055/a-1509-8624
DOI: 10.1055/a-1509-8624
paper
Direct Approach to 3-Fluoroindoles and 3,3-Difluoroindolines from 2,2-Difluoro-2-phenylethan-1-amines via C–H/N–H Coupling
Authors
This work was supported by grants from Science and Technology Commission of Shanghai Municipality (18431907100), and by the State Key Laboratory of Drug Research (SIMM193ZZ-03).
Abstract
Herein, a direct method for the synthesis of 3-fluoroindoles and 3,3-difluoroindolines from easily accessible 2,2-difluoro-2-phenylethan-1-amines is presented. This protocol was performed by Pd-catalyzed direct C–H/N–H coupling and employed picolinamide as a directing group. By controlling the temperature for this transformation, various 3,3-difluoroindolines and 3-fluoroindoles could be isolated with moderate to good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1509-8624.
- Supporting Information (PDF)
Publication History
Received: 21 April 2021
Accepted after revision: 17 May 2021
Accepted Manuscript online:
17 May 2021
Article published online:
15 June 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Qin M, Cao Q, Wu X, Liu C, Zheng S, Xie H, Tian Y, Xie J, Zhao Y, Hou Y, Zhang X, Xu B, Zhang H, Wang X. Eur. J. Med. Chem. 2020; 186: 111856
- 1b Wang S.-Y, Shi X.-C, Laborda P. Eur. J. Med. Chem. 2020; 185: 111847
- 1c Zhu Y, Sun N, Yu M, Guo H, Xie Q, Wang Y. Eur. J. Org. Chem. 2019; 111589
- 1d Melander RJ, Minvielle MJ, Melander C. Tetrahedron 2014; 70: 6363
- 1e Sibel S. Curr. Org. Chem. 2017; 21: 2068
- 1f Zeeli S, Weill T, Finkin-Groner E, Bejar C, Melamed M, Furman S, Zhenin M, Nudelman A, Weinstock M. J. Med. Chem. 2018; 61: 4004
- 2 Teena S, Sanjiv K, Balasubramanian N. Cent. Nerv. Syst. Agents Med. Chem. 2016; 16: 19
- 3 Namasivayam V, Vanangamudi M, Kramer VG, Kurup S, Zhan P, Liu X, Kongsted J, Byrareddy SN. J. Med. Chem. 2019; 62: 4851
- 4 Drayson P, Mahdi A, Tarassenko L, Watkinson P. WO2019211632A1, 2019
- 5a Yu Y, Zhong J.-S, Xu K, Yuan Y, Ye K.-Y. Adv. Synth. Catal. 2020; 362: 2102
- 5b Neto JS. S, Zeni G. Org. Chem. Front. 2020; 7: 155
- 5c Nagaraju K, Ma D. Chem. Soc. Rev. 2018; 47: 8018
- 5d Mondal D, Kalar PL, Kori S, Gayen S, Das K. Curr. Org. Chem. 2020; 24: 2665
- 5e Colella M, Degennaro L, Luisi R. Molecules 2020; 25: 3242
- 5f Christodoulou MS, Beccalli EM, Foschi F, Giofre S. Synthesis 2020; 52: 2731
- 5g Aggarwal T, Sushmita, Verma AK. Org. Biomol. Chem. 2019; 17: 8330
- 6 Wang J, Sanchez-Rosello M, Acena JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
- 7 Zimmer LE, Sparr C, Gilmour R. Angew. Chem. Int. Ed. 2011; 50: 11860
- 8 Nazaré M, Will DW, Matter H, Schreuder H, Ritter K, Urmann M, Essrich M, Bauer A, Wagner M, Czech J, Lorenz M, Laux V, Wehner V. J. Med. Chem. 2005; 48: 4511
- 9 Young BL, Cooks RG, Madden MC, Bair M, Jia J, Aubry A.-F, Miller SA. J. Pharm. Biomed. Anal. 2007; 43: 1602
- 10 Ma C, Gao P, Chu J, Wu X, Wen C, Kang D, Bai J, Pei X. WO2017211303A1, 2017
- 11a Zhang B, Zhang X, Hao J, Yang C. Org. Lett. 2017; 19: 1780
- 11b Zeidan N, Zambri M, Unger S, Dank C, Torelli A, Mirabi B, Lautens M. Org. Lett. 2020; 22: 3688
- 11c Fujita T, Sugiyama K, Sanada S, Ichitsuka T, Ichikawa J. Org. Lett. 2016; 18: 248
- 11d Nosova EV, Lipunova GN, Charushin VN, Chupakhin ON. J. Fluorine Chem. 2018; 212: 51
- 11e Fujita T, Watabe Y, Yamashita S, Tanabe H, Nojima T, Ichikawa J. Chem. Lett. 2016; 45: 964
- 12a Torres J, Garden SJ, Pinto AC, da Silva FS. Q, Boechat N. Tetrahedron 1999; 55: 1881
- 12b Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
- 12c Yang L, Ma Y, Song F, You J. Chem. Commun. 2014; 50: 3024
- 12d Jiang X, Zhang F, Yang J, Yu P, Yi P, Sun Y, Wang Y. Adv. Synth. Catal. 2017; 359: 853
- 12e Yuan X, Yao JF, Tang ZY. Org. Lett. 2017; 19: 1410
- 12f Panferova LI, Smirnov VO, Levin VV, Kokorekin VA, Struchkova MI, Dilman AD. J. Org. Chem. 2017; 82: 745
- 12g Bora PP, Bihani M, Plummer S, Gallou F, Handa S. ChemSusChem 2019; 12: 3037
- 13a Li J, Zhang X, Xiang H, Tong L, Feng F, Xie H, Ding J, Yang C. J. Org. Chem. 2017; 82: 6795
- 13b Zhang X, Yang C. Adv. Synth. Catal. 2015; 357: 2721
- 13c Xiang H, Yang C. Org. Lett. 2014; 16: 5686
- 14a Karnakanti S, Zang ZL, Zhao S, Shao PL, Hu P, He Y. Chem. Commun. 2017; 53: 11205
- 14b Xu J, Qiao L, Shen J, Chai K, Shen C, Zhang P. Org. Lett. 2017; 19: 5661
- 14c Landge VG, Midya SP, Rana J, Shinde DR, Balaraman E. Org. Lett. 2016; 18: 5252
- 14d Yu X, Yang F, Wu Y, Wu Y. Org. Lett. 2019; 21: 1726
- 14e Rej S, Chatani N. ACS Catal. 2018; 8: 6699
- 14f Parella R, Babu SA. J. Org. Chem. 2017; 82: 6550
- 14g Mao CL, Zhao S, Zang ZL, Xiao L, Zhou CH, He Y, Cai GX. J. Org. Chem. 2020; 85: 774
- 14h Aleman-Ponce de Leon D, Sanchez-Chavez AC, Polindara-Garcia LA. J. Org. Chem. 2019; 84: 12809
- 14i Lukasevics L, Cizikovs A, Grigorjeva L. Org. Lett. 2020; 22: 2720
- 14j Kuai C, Wang L, Li B, Yang Z, Cui X. Org. Lett. 2017; 19: 2102
- 14k Biswas S, Bheemireddy NR, Bal M, Van Steijvoort BF, Maes BU. W. J. Org. Chem. 2019; 84: 13112
- 15a Usui K, Haines BE, Musaev DG, Sarpong R. ACS Catal. 2018; 8: 4516
- 15b He G, Lu C, Zhao Y, Nack WA, Chen G. Org. Lett. 2012; 14: 2944
- 16a Kreutter KD, Lu T, Lee L, Giardino EC, Patel S, Huang H, Xu G, Fitzgerald M, Haertlein BJ, Mohan V, Crysler C, Eisennagel S, Dasgupta M, McMillan M, Spurlino JC, Huebert ND, Maryanoff BE, Tomczuk BE, Damiano BP, Player MR. Bioorg. Med. Chem. Lett. 2008; 18: 2865
- 16b Mizuta S, Stenhagen IS. R, O’Duill M, Wolstenhulme J, Kirjavainen AK, Forsback SJ, Tredwell M, Sandford G, Moore PR, Huiban M, Luthra SK, Passchier J, Solin O, Gouverneur V. Org. Lett. 2013; 15: 2648