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 2012; 44(12): 1874-1884
DOI: 10.1055/s-0031-1290950
DOI: 10.1055/s-0031-1290950
special topic
Synthesis of 2-Indol-3-ylbenzofulvenes through a Tandem Reaction Catalyzed by Cationic Gold(I) Complexes
Further Information
Publication History
Received: 08 March 2012
Accepted: 30 March 2012
Publication Date:
04 May 2012 (online)
Dedicated to our good friend Professor Francisco J. Fañanás on the occasion of his 60th birthday
Abstract
A new access to benzofulvenes bearing an indol-3-yl substituent at C-2 has been developed. Treatment of 3-propargylindoles possessing an additional hydroxy group at the other propargylic position with a cationic gold(I) complex triggers a tandem 1,2-indole migration/aura-iso-Nazarov cyclization/elimination sequence that takes place under mild conditions.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 New address: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
- 2a Tietze LF. Chem. Rev. 1996; 96: 115
- 2b Tietze LF, Brasche G, Gericke K. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006: 672
- 2c Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
- 3a Mayer SF, Kroutil W, Faber K. Chem. Soc. Rev. 2001; 30: 332
- 3b McCarroll AJ, Walton JC. Angew. Chem. Int. Ed. 2001; 40: 2224
- 3c Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem. Int. Ed. 2006; 45: 7134
- 4a Fogg DE, dos Santos EN. Coord. Chem. Rev. 2004; 248: 2365
- 4b Shindoh N, Takemoto Y, Takasu K. Chem.–Eur. J. 2009; 15: 12168
- 5 Bruggink A, Schoevaart R, Kieboom T. Org. Process Res. Dev. 2003; 7: 622
- 6 For a recent review, see: Vlaar T, Ruijter E, Orru RV. A. Adv. Synth. Catal. 2011; 353: 809
-
For recent reviews, see:
- 7a Nolan SP. Acc. Chem. Res. 2011; 44: 91
- 7b Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
- 7c Krause N, Winter C. Chem. Rev. 2011; 111: 1994
- 7d Wegner HA, Auzias M. Angew. Chem. Int. Ed. 2011; 50: 8236
- 7e Hopkinson MN, Gee AD, Gouverneur V. Chem.–Eur. J. 2011; 17: 8242
-
For recent examples of Au(I)-catalyzed tandem reaction initiated by migration of propargyl esters, see:
- 8a Zhang D.-H, Yao L.-F, Wei Y, Shi M. Angew. Chem. Int. Ed. 2011; 50: 2583
- 8b Lebœuf D, Simonneau A, Aubert C, Malacria M, Gandon V, Fensterbank L. Angew. Chem. Int. Ed. 2011; 50: 6868
- 8c Rao W, Susanti D, Chan PW. H. J. Am. Chem. Soc. 2011; 133: 15248
-
See, for example:
- 9a Nakano T, Takewaki K, Yade T, Okamoto Y. J. Am. Chem. Soc. 2001; 123: 9182
- 9b Cappelli A, Mohr GP, Anzini M, Vomero S, Donati A, Casolaro M, Mendichi R, Giorgi G, Makovec F. J. Org. Chem. 2003; 68: 9473
- 10 Alt HG, Köppl A. Chem. Rev. 2000; 100: 1205
- 11a Wang S, Yang Q, Mak TC. W, Xie Z. Organometallics 2000; 19: 334
- 11b Kovalenko SV, Peabody S, Manoharan M, Clark RJ, Alabugin IV. Org. Lett. 2004; 6: 2457
- 12 See, for instance: Clegg NJ, Paruthiyil S, Leitman DC, Scanlan TS. J. J. Med. Chem. 2005; 48: 5989
-
For selected recent benzofulvene syntheses from monocyclic precursors, see:
- 13a Lee C.-Y, Wu M.-J. Eur. J. Org. Chem. 2007; 3463
- 13b Bucher G, Mahajan AA, Schmittel M. J. Org. Chem. 2008; 73: 8815
- 13c Cordier P, Aubert C, Malacria M, Lacôte E, Gandon V. Angew. Chem. Int. Ed. 2009; 48: 8757
- 13d Jeffrey JL, Sarpong R. Tetrahedron Lett. 2009; 50: 1969
- 13e Ye S, Gao K, Zhou H, Yang X, Wu J. Chem. Commun. 2009; 5406
- 13f Bryan CS, Lautens M. Org. Lett. 2010; 12: 2754
- 13g Ye S, Yang X, Wu J. Chem. Commun. 2010; 46: 2950
- 13h Tsuchikama K, Kasagawa M, Endo K, Shibata T. Synlett 2010; 97
- 13i Chinnagolla RK, Jeganmohan M. Eur. J. Org. Chem. 2012; 417
- 14a Sanz R, Miguel D, Álvarez-Gutiérrez JM, Rodríguez F. Synlett 2008; 975
- 14b Sanz R, Miguel D, Martínez A, Gohain M, García-García P, Fernández-Rodríguez MA, Álvarez E, Rodríguez F. Eur. J. Org. Chem. 2010; 7027
- 15a Sanz R, Miguel D, Rodríguez F. Angew. Chem. Int. Ed. 2008; 47: 7354
- 15b Sanz R, Miguel D, Gohain M, García-García P, Fernández-Rodríguez MA, González-Pérez A, Nieto-Faza O, de Lera AR, Rodríguez F. Chem.–Eur. J. 2010; 16: 9818
- 16 The selectivity of this tandem reaction (1,2-migration followed by aura-iso-Nazarov cyclization) could be switched by the proper choice of catalyst and reaction conditions allowing the isolation of 2-(inden-3-yl)indenes derived from an aura-Nazarov cyclization. See: Álvarez E, Miguel D, García-García P, Fernández-Rodríguez MA, Rodríguez F, Sanz R. Beilstein J. Org. Chem. 2011; 7: 786
- 17a Marion N, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2750
- 17b Marco-Contelles J, Soriano E. Chem. Eur. J. 2007; 13: 1350
- 17c Wang S, Zhang G, Zhang L. Synlett 2010; 692
- 18a Martínez A, García-García P, Fernández-Rodríguez MA, Rodríguez F, Sanz R. Angew. Chem. Int. Ed. 2010; 49: 4633
- 18b Sanz R, Martínez A, García-García P, Fernández-Rodríguez MA, Rashid MA, Rodríguez F. Chem. Commun. 2010; 46: 7427
- 19 Mézailles N, Ricard L, Gagosz F. Org. Lett. 2005; 7: 4133
- 20 The stereochemistry of the double bond was assigned by NOESY experiments. See Supporting Information
- 21 CCDC 869753 (5c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif