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
Synthesis 2022; 54(20): 4561-4575
DOI: 10.1055/a-1863-3443
DOI: 10.1055/a-1863-3443
paper
Gram-Scale Synthesis of Substituted Triarylmethanes
The authors would like to thank the Ministry of Science and Technology of the Republic of China (Taiwan) for the financial support (MOST 109-2113-M-037-014-MY3).
Abstract
A high-yield, open-vessel route for the facile-operational, gram-scale synthesis of functionalized triarylmethanes (TRAMs) is described via silica-coated magnetic nanoparticles of modified polyphosphoric acid (NiFe2O4@SiO2-PPA)-mediated intermolecular Friedel–Crafts reaction of substituted aryl aldehydes with 2 equivalents of oxygenated arenes under environmentally friendly reaction conditions. Among the overall reaction process, only water was generated as the by-product. Various reaction conditions are investigated for efficient transformation.
Key words
gram-scale synthesis - triarylmethanes - magnetic nanoparticles - Friedel–Crafts reaction - environmentally friendlySupporting Information
- Scanned photocopies of NMR spectral data for all compounds and X-ray analysis data of 4e and 4ah-1. Supporting information for this article is available online at https://doi.org/10.1055/a-1863-3443.
- Supporting Information
Publication History
Received: 26 April 2022
Accepted after revision: 27 May 2022
Accepted Manuscript online:
27 May 2022
Article published online:
21 July 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Duxbury DF. Chem. Rev. 1993; 93: 381
- 2 Shchepinov MS, Korshun VA. Chem. Soc. Rev. 2003; 32: 170
- 3 Nair V, Thomas S, Mathew SC, Abhilash KG. Tetrahedron 2006; 62: 6731
- 4 Mondal S, Panda G. RSC Adv. 2014; 4: 28317
- 5 Nambo M, Crudden CM. ACS Catal. 2015; 5: 4734
- 6a Kshatriya R, Jejurkar VP, Saha S. Eur. J. Org. Chem. 2019; 3818
- 6b Liu X, Wu X, Zhang L, Lin X, Huang D. Synthesis 2020; 52: 2311
- 6c Irfana JC. P. A, Mercy AH, Ravindra S, Kataria R, Nandi GC. J. Org. Chem. 2020; 85: 3000
- 7 Kraus GA, Jeon I, Nilsen-Hamilton MA, Awad M, Banerjee J, Parvin B. Molecules 2008; 13: 986
- 8 Wilsdorf M, Leichnitz D, Reissig H.-U. Org. Lett. 2013; 15: 2494
- 9 Li H, Yang J, Liu Y, Li Y. J. Org. Chem. 2009; 74: 6797
- 10 Periasamy M, Jayakumar KN, Bharathi P. J. Org. Chem. 2000; 65: 3548
- 11 Rodrigues SM. M, Previdi D, Baviera GS, Matias AA, Donate PM. Synthesis 2019; 51: 4498
- 12 Bardajee GR. Beilstein J. Org. Chem. 2011; 7: 135
- 13 Wang X, Wang Y, Du DM, Xu J. J. Mol. Catal. A: Chem. 2006; 255: 31
- 14a Nair V, Abhilash KG, Vidya N. Org. Lett. 2005; 7: 5857
- 14b Nair V, Vidya N, Abhilash KG. Synthesis 2006; 3647
- 15 Kothandapani J, Ganesan A, Vairaprakash P, Ganesan SS. Tetrahedron Lett. 2015; 56: 2238
- 16 Podder S, Choudhury J, Roy UK, Roy S. J. Org. Chem. 2007; 72: 3100
- 17 Reddy CS, Nagaraj A, Srinivas A, Reddy GP. Indian J. Chem. 2009; 48B: 248
- 18 An LT, Ding FQ, Zou JP. Dyes Pigments 2008; 77: 478
- 19 Singh K, Sharma S, Sharma A. J. Mol. Catal. A: Chem. 2011; 347: 34
- 20 Prakash GK. S, Fogassy G, Olah GA. Catal. Lett. 2010; 138: 155
- 21 Bachhav HM, Takale BS, Telvekar VN. Synth. Commun. 2013; 43: 1909
- 22 Jaratjaroonphong J, Sathalalai S, Techasauvapak P, Reutrakul V. Tetrahedron Lett. 2009; 50: 6012
- 23 Shanmuga P, Varma L. Indian J. Chem. Sect. B 2001; 40B: 1258
- 24 Kang LQ, Gao H, Cai YQ. Monatsh. Chem. 2018; 149: 57
- 25 Pasha MA, Nagashree S. Int. J. Res. Chem. Environ. 2013; 3: 54
- 26 Lim CW, Lee IS. Nano Today 2010; 5: 412
- 27 Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset JM. Chem. Rev. 2011; 111: 3036
- 28 Li S, Lin MM, Kim HH, Topark MS, Kim DK, Muhammed M. Nano Rev. 2010; 1: 4883
- 29 Astruc D, Lu F, Aranzaes JR. Angew. Chem. Int. Ed. 2005; 44: 7852
- 30 Yamada M, Arisawa M. Tetrahedron Lett. 2020; 61: 151422
- 31 Lin J.-S, Li T.-T, Liu J.-R, Jiao G.-Y, Gu Q.-S, Cheng J.-T, Guo Y.-L, Hong X, Liu X.-Y. J. Am. Chem. Soc. 2019; 14: 1074
- 32 Yue C, Na F, Fang X, Cao Y, Antilla JC. Angew. Chem. Int. Ed. 2018; 57: 11004
- 33 Wong YF, Wang Z, Sun J. Org. Biomol. Chem. 2016; 14: 5751
- 34 Saha S, Alamsetti SK, Schneider C. Chem. Commun. 2015; 51: 1461
- 35 Zhuo M.-H, Jiang Y.-J, Fan Y.-S, Gao Y, Liu S, Zhang S. Org. Lett. 2014; 16: 1096
- 36 Zhang Z, Wang H, Qiu N, Kong Y, Zeng W, Zhang Y, Zhao J. J. Org. Chem. 2018; 83: 8710
- 37 Zhang J, Bellomo A, Creamer AD, Dreher SD, Walsh PJ. J. Am. Chem. Soc. 2012; 134: 13765
- 38a Eshghi H, Khojastehnezhad A, Moeinpour F, Bakavoli M, Zeinabi N, Allameh S. Res. Chem. Intermed. 2015; 41: 7915
- 38b Chaudhuri A, Mandal M, Mandal K. J. Alloys Compd. 2009; 487: 698
- 39 Khojastehnezhad A, Moeinpour F, Javid A. Polycycl. Aromat. Comp. 2019; 39: 404
- 40 Moeinpour F, Khojastehnezhad A. Arabian J. Chem. 2017; 10: S3468
- 41 Vajar S, Mokhtary M. Polycycl. Aromat. Comp. 2019; 39: 111
- 42 Vekariya RH, Prajapati NP, Patel HD. Synth. Commun. 2016; 46: 197
- 43 CCDC 1981539 (4e) and 1981540 (4ah-1) contain 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
- 44 Li P, Huang Y, Hu X, Dong X.-Q, Zhang X. Org. Lett. 2017; 19: 3855
- 45 Balakrishna B, Bauzá A, Frontera A, Vidal-Ferran A. Chem. Eur. J. 2016; 22: 10607
- 46 Fischer-Cornelssen KA. Arzneimittelforschung 1984; 34: 125
- 47 Woggon B, Angst J, Bartels M, Heinrich K, Hippius H, Koukkou M, Krebs E, Kufferle B, Muller-Oerlinghausen B, Poldinger W. Neuropsychobiology 1984; 11: 116