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-00000083.xml
Synlett 2016; 27(19): 2689-2694
DOI: 10.1055/s-0036-1588302
DOI: 10.1055/s-0036-1588302
letter
Organopromoted Direct Synthesis of 1,1-Diphenyl-3-arylindanes via Formal [3+2] Cycloadditions of Triphenylcarbenium Tetrafluoroborate with Styrenes
Weitere Informationen
Publikationsverlauf
Received: 12. Juni 2016
Accepted after revision: 05. August 2016
Publikationsdatum:
29. August 2016 (online)
Abstract
A formal [3+2] cycloaddition of triphenylcarbenium tetrafluoroborate with structurally different styrene derivatives has been developed. A combination of benzophenone and Et3N is key for promoting a formal [3+2] cycloaddition of triphenylcarbenium tetrafluoroborate with styrenes affording 1,1-diphenyl-3-arylindanes in moderate to good yields. The reaction mechanism of this transformation is also discussed.
Key words
styrenes - triphenylcarbenium tetrafluoroborate - indanes - formal [3+2] cycloaddition - organocatalystSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588302.
- Supporting Information
-
References and Notes
- 1a DeSolms SJ, Woltersdorf OW. Jr, Cragoe EJ. Jr. J. Med. Chem. 1978; 21: 437
- 1b Bøgesø KP, Christensen AV, Hyttel J, Liljefors T. J. Med. Chem. 1985; 28: 1817
- 1c Dorsey BD, Levin RB, McDaniel SL, Vacca JP, Guare JP, Darke PL, Zugay JA, Emini EA, Schleif WA, Quintero JC, Lin JH, Chen I.-W, Holloway MK, Fitzgerald PM. D, Axel MG, Ostovic D, Anderson PS, Huff JR. J. Med. Chem. 1994; 37: 3443
- 1d Sugimoto H, Iimura Y, Yamanishi Y, Yamatsu K. J. Med. Chem. 1995; 38: 4821
- 2 Carta M, Msayib KJ, Budd PM, McKeown NB. Org. Lett. 2008; 10: 2641
- 3a MacKenzie H, Budd PM, McKeown NB. J. Mater. Chem. 2008; 18: 573
- 3b Budd PM, Ghanem B, Msayib K, McKeown NB, Tattershall C. J. Mater. Chem. 2003; 13: 2721
- 4a McKeown NB, Gahnem B, Msayib KJ, Budd PM, Tattershall CE, Mahmood K, Tan S, Book D, Langmi HW, Walton A. Angew. Chem. Int. Ed. 2006; 45: 1804
- 4b Budd PM, Butler A, Selbie J, Mahmood K, McKeown NB, Ghanem B, Msayib K, Book D, Walton A. Phys. Chem. Chem. Phys. 2007; 9: 1802
- 4c Ghanem BS, Msayid KJ, McKeown NB, Harris KD. M, Pan Z, Budd PM, Butler A, Selbie J, Book D, Walton A. Chem. Commun. 2007; 67
- 4d McKeown NB, Budd PM, Book D. Macromol. Rapid Commun. 2007; 28: 995
- 5 Budd PM, Elabas ES, Ghanem BS, Makhseed S, McKeown NB, Msayib KJ, Tattershall CE, Wang D. Adv. Mater. 2004; 16: 456
- 6a Angle SR, Arnaiz DO. J. Org. Chem. 1992; 57: 5937
- 6b Katritzky AR, Zhang G, Xie L. Synth. Commun. 1997; 27: 2467
- 6c Lantaño B, Aguirre JM, Finkielsztien L, Alesso EN, Brunet E, Moltrasio GY. Synth. Commun. 2004; 34: 625
- 6d Lantaño B, Aguirre JM, Ugliarolo EA, Benegas ML, Moltrasio GY. Tetrahedron 2008; 64: 4090
- 7 Khalaf AA, EI-Khawaga AM, Awad IM, Abd El-AalH. A. K. Arkivoc 2009; (xiv): 314
- 8a Madhavan D, Murugalakshmi M, Lalitha A, Pitchumani K. Catal. Lett. 2001; 73: 1
- 8b Ciminale F, Lopez L, Farinola GM, Sportelli S, Nacci A. Eur. J. Org. Chem. 2002; 3850
- 8c Peppe C, Lang ES, de Andrade FM, de Castro LB. Synlett 2004; 1723
- 8d Sun H.-B, Li B, Hua R, Yin Y. Eur. J. Org. Chem. 2006; 4231
- 9a Hixson SS, Franke LA. J. Org. Chem. 1988; 53: 2706
-
9b Miyaura N, Ishiyama T, Sasaki H, Ishikawa M, Satoh M, Suzuki A. J. Am. Chem. Soc. 1989; 111: 314
- 9c Bailey WF, Longsfaff SC. J. Org. Chem. 1998; 63: 432
- 9d Ruan J, Iggo JA, Xiao J. Org. Lett. 2011; 13: 268
- 10 Ducharme Y, Latour S, Wuest JD. Organometallics 1984; 3: 208
- 11 Wu I.-Y, Tsai J.-H, Huang B.-C, Chen S.-C, Lin Y.-C. Organometallics 1993; 12: 3971
- 12 Acar MH, Küçüköner M. Polymer 1997; 38: 2829
- 13 Auricchio S, Magnani C, Truscello AM. Eur. J. Org. Chem. 2002; 2411
- 14 Morkovnik AS, Suslov AN, Klimov ES, Morkovnik ZS, Okhlobystin OY. Chem. Heterocycl. Compd. 1995; 31: 847
- 15 Zhang X.-M, Yang D.-L, Liu Y.-C. J. Org. Chem. 1993; 58: 224
- 16 General Procedure for the Synthesis of 1,1,3-Triphenylindane (6a) A round-bottom flask equipped with a magnetic stirrer bar was charged with styrene (1.0 mmol), benzophene (0.3 mmol), Et3N (1.0 mmol), and toluene (2.5 mL). Triphenylcarbenium tetrafluoroborate (1.5 mmol) was then added, and the resulting mixture was allowed to react at 80 °C for 48 h. After the end of the reaction, the mixture was filtered through a plug of Celite® and eluted with hexane–EtOAc (8:2). The filtrate was concentrated in vacuo and purified by column chromatography on silica gel. The final product 6a was obtained in 77% yield as a white solid, mp 111.5–112.5 °C. Analytical TLC on silica gel: R ƒ = 0.40 (hexanes–EtOAc = 9.9:0.1). IR (KBr): νmax = 3080, 3061, and 3025 (aromatic), 2966, 2928, and 2862 (CH of aliphatic), 1596, and 1491 (aromatic), 1470, 1454, and 1444 (CH of aliphatic) cm–1. 1H NMR (300 MHz, CDCl3): δ = 7.35–7.16 (m, 17 H), 7.1 (d, J = 6.8 Hz, 1 H), 6.92 (d, J = 6.8 Hz, 1 H), 4.2 (dd, J = 6.4, 11.1 Hz, 1 H), 3.2 (dd. J = 6.4, 12.6 Hz, 1 H), 2.90 (dd, 11.1, 12.6 Hz, 1 H). 13C NMR (75 MHz, CDCl3): δ = 149.41 (C), 148.05 (C), 146.66, (C), 145.83 (C), 143.88 (C), 128.61 (3 CH), 128.54 (3 CH), 128.52 (2 CH), 128.03 (2 CH), 127.99 (2 CH), 127.19 (CH), 126.72 (CH), 126.62 (CH), 126.28 (CH), 126.08 (CH), 126.04 (CH), 125.03 (CH), 60.84 (C), 54.13 (CH2), 49.01 (CH). HRMS (ESI-TOF): m/z [M + Na]+ calcd for C27H22Na: 369.1619; found: 369.1531.