Solvent-Free Iridium(III)-Catalyzed [2+2+2] Cycloaddition Providing Access to Fused Arenes: Isoindolines, Dihydroisobenzofurans and Indanes

Abstract

A practical and convenient solvent-free iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes and alkynes to prepare fused arenes has been developed. The method has shown high efficiency as isoindolines, dihydroisobenzofurans and indanes have been synthesized in good to excellent yields.

Keywords

cycloadditions - iridium - atom economy - solvent-free conditions - benzannulation

• References


For selected reviews on reactions under environmentally friendly and solvent-free conditions, see:
• 1a Tanaka K. Solvent-Free Organic Synthesis . Wiley-VCH; Weinheim: 2003
• 1b Tanaka K, Toda F. Chem. Rev. 2000; 100: 1025
• 1c Metzger JO. Angew. Chem. Int. Ed. 1998; 37: 2975
• 1d Cave GW. V, Raston CL, Scott JL. Chem. Commun. 2001; 2159
• 1e Walsh PJ, Li H, de Parrodi CA. Chem. Rev. 2007; 107: 2503
• 1f Marvaniya HM, Modi KN, Sen DJ. Int. J. Drug Dev. Res. 2011; 3 (02) 34
• 1g Varma RS. Green Chem. 1999; 1: 43
• 1h Capello C, Fischer U, Hungerbühler K. Green Chem. 2007; 9: 927
• 1i Keith LH, Gron LU, Young JL. Chem. Rev. 2007; 107: 2695
• 1j Genin E, Leseurre L, Michelet V In Génie des procédés verts et durables: outils et méthodes . Poux M, Cognet P, Gourdon C. Dunod; Paris: 2009: 276
• 2a Saito S, Yamamoto Y. Chem. Rev. 2000; 100: 2901
• 2b Rubin M, Sromek AW, Gevorgyan V. Synlett 2003; 2265
• 2c D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
• 3a Kotha S, Brahmachary E, Lahiri K. Eur. J. Org. Chem. 2005; 4741
• 3b Yamamoto Y. Curr. Org. Chem. 2005; 9: 503
• 3c Gandon V, Aubert C, Malacria M. Chem. Commun. 2006; 2209
• 3d Gandon V, Aubert C, Malacria M. Curr. Org. Chem. 2005; 9: 1699
• 3e Chopade PR, Louie J. Adv. Synth. Catal. 2006; 348: 2307
• 3f Leboeuf D, Gandon V, Malacria M. Transition Metal-Mediated [2+2+2] Cycloadditions . In Handbook of Cyclization Reactions . Vol. 1. Ma S. Wiley-VCH; Weinheim: 2009: 367-406
• 3g Haughton L, Williams JM. J. J. Chem. Soc., Perkin Trans. 1 1999; 2645
• 3h Weding N, Hapke M. Chem. Soc. Rev. 2011; 40: 4525
• 3i Inglesby PA, Evans PA. Chem. Soc. Rev. 2010; 39: 2791
• 3j Domingez G, Pérez-Castells J. Chem. Soc. Rev. 2011; 40: 3430
• 4a Kezuka S, Tanaka S, Ohe T, Nakaya Y, Takeuchi R. J. Org. Chem. 2006; 71: 543
• 4b Shanmugasundaram M, Aguirre AL, Leyva M, Quan B, Martinez LE. Tetrahedron Lett. 2007; 48: 7698
• 4c Matsuda T, Kadowaki S, Goya T, Murakami M. Org. Lett. 2007; 9: 133
• 4d Onodera G, Matsuzawa M, Aizawa T, Kitahara T, Shimizu Y, Kezuka S, Takeuchi R. Synlett 2008; 755
• 4e Takeuchi R, Nakaya Y. Org. Lett. 2003; 5: 3659
• 4f Takeuchi R, Tanaka S, Nakaya Y. Tetrahedron Lett. 2001; 42: 2991

For the enantioselective iridium-catalyzed preparation of polyaromatics, see:
• 4g Shibata T, Yoshida S, Arai Y, Otsuka M, Endo K. Tetrahedron 2008; 64: 821
• 4h Shibata T, Arai Y, Takami K, Tsuchikama K, Fujimoto T, Takebayashi S, Takagi K. Adv. Synth. Catal. 2006; 348: 2475
• 4i Shibata T, Tsuchikama K, Otsuka M. Tetrahedron: Asymmetry 2006; 17: 614
• 4j Shibata T, Tsuchikama K. Chem. Commun. 2005; 6017
• 4k Shibata T, Fujimoto T, Yokota K, Takagi K. J. Am. Chem. Soc. 2004; 126: 8382
• 5a Yamagata T, Tadaoka H, Nagata M, Hirao T, Kataoka Y, Ratovelomanana-Vidal V, Genêt J.-P, Mashima K. Organometallics 2006; 25: 2505
• 5b Deport C, Buchotte M, Abecassis K, Tadaoka H, Ayad T, Ohshima T, Genêt J.-P, Mashima K, Ratovelomanana-Vidal V. Synlett 2007; 2743
• 5c Cartigny D, Nagano T, Ayad T, Genêt J.-P, Ohshima T, Mashima K, Ratovelomanana-Vidal V. Adv. Synth. Catal. 2010; 352: 1886
• 5d Tadaoka H, Cartigny D, Nagano T, Gosavi T, Ayad T, Genêt J.-P, Ohshima T, Ratovelomanana-Vidal V, Mashima K. Chem. Eur. J. 2009; 15: 9990
• 5e Ez-Zoubir M, Le Boucher d’Herouville F, Brown J, Ratovelomanana-Vidal V, Michelet V. Chem. Commun. 2010; 46: 6332
• 5f Cartigny D, Berhal F, Nagano T, Phansavath P, Ayad T, Genet J.-P, Ohshima T, Mashima K, Ratovelomanana-Vidal V. J. Org. Chem. 2012; 77: 4544
• 6a Auvinet A.-L, Ez-Zoubir M, Vitale MR, Brown JA, Michelet V, Ratovelomanana-Vidal V. ChemSusChem 2012; 5: 1888
• 6b Auvinet A.-L, Ez-Zoubir M, Vitale MR, Brown JA, Michelet V, Ratovelomanana-Vidal V. ChemCatChem 2013; in press; DOI: 10.1002/cctc.201300068
• 7a Eissen ME, Metzger JO, Schmidt E, Schneidewind U. Angew. Chem. Int. Ed. 2002; 41: 414
• 7b Green Chemistry: Theory and Practice . Anastas PT, Warner JC. Oxford University Press; New York: 1998: 15
• 8 Bonfield ER, Li C.-J. Adv. Synth. Catal. 2008; 350: 370
• 9a Favor DA, Powers JJ, Repine JT, White AD (Pfizer) WO2008/020306A2, 2008
• 9b Gallagher NJ, Lyons JF, Thompson NT, Yule SM, Murray CW (Astex Pharmaceuticals) WO2008/044029A1, 2008
• 10 Kinoshita H, Shinokubo H, Oshima K. J. Am. Chem. Soc. 2003; 125: 7784
• 11 Horiuchi T, Nagata M, Kitagawa M, Akahane K, Uoto K. Bioorg. Med. Chem. 2009; 17: 7850