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 2013; 45(1): 118-126
DOI: 10.1055/s-0032-1317849
DOI: 10.1055/s-0032-1317849
paper
Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethylindenes
Further Information
Publication History
Received: 20 September 2012
Accepted after revision: 19 November 2012
Publication Date:
11 December 2012 (online)
Abstract
A palladium-catalyzed tandem carbocyclization–Suzuki coupling is described leading to the synthesis of trifluoromethyl-containing indenes in moderate to good yields. The reactions take place in the presence of palladium(II) acetate, a phosphorus-containing ligand [dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine] and potassium carbonate in toluene as the solvent. The process occurs via intramolecular carbocyclization and subsequent Suzuki coupling of the ortho-(2-chlorovinyl)-alkynylbenzenes with arylboronic acids.
-
References
- 1a Majetich G, Shimkus JM. J. Nat. Prod. 2010; 73: 284
- 1b Lee BH, Choi YL, Shin S, Heo JN. J. Org. Chem. 2011; 76: 6611
- 2a Gao H, Katzenellenbogen JA, Garg R, Hansch C. Chem. Rev. 1999; 99: 723
- 2b Korte A, Legros J, Bolm C. Synlett 2004; 2397
- 2c Alcalde E, Mesquida N, López-Pérez S, Frigola J, Mercè R. J. Med. Chem. 2009; 52: 675
- 2d Solomak T, Stacko P, Veetil AT, Pospisil T, Klan P. J. Org. Chem. 2010; 75: 7300
- 3a Akbulut U, Khurshid A, Hacioglu B, Toppare L. Polymer 1990; 31: 1343
- 3b Barbera J, Rakitin OA, Ros MB, Torroba T. Angew. Chem. Int. Ed. 1998; 37: 296
- 3c Yang J, Lakshmikantham MV, Cava MP, Lorcy D, Bethelot JR. J. Org. Chem. 2000; 65: 6739
- 4a Alt HG, Köppl A. Chem. Rev. 2000; 100: 1205
- 4b Kim DH, Lee JA, Lee BY, Chung YK. J. Organomet. Chem. 2005; 690: 1822
- 4c Izmer VV, Lebedev AY, Nikulin MV, Ryabov AN, Asachenko AF, Lygin AV, Sorokin DA, Voskoboynikov AZ. Organometallics 2006; 25: 1217
- 5a Wang S, Zhu Y, Wang Y, Lu P. Org. Lett. 2009; 11: 2615
- 5b Ye S, Gao K, Zhou H, Yang X, Wu J. Chem. Commun. 2009; 5406
- 5c Tran DN, Cramer N. Angew. Chem. Int. Ed. 2011; 50: 11098
- 5d Zhou F, Han X, Lu X. J. Org. Chem. 2011; 76: 1491
- 6a Schreiner PR, Prall M, Lutz V. Angew. Chem. Int. Ed. 2003; 42: 5757
- 6b Bekele T, Christian CF, Lipton MA, Singleton DA. J. Am. Chem. Soc. 2005; 127: 9216
- 6c Furuta T, Asakawa T, Iinuma M, Fujii S, Tanaka K, Kan T. Chem. Commun. 2006; 3648
- 6d Rahman SM. A, Sonoda M, Ono M, Miki K, Tobe Y. Org. Lett. 2006; 8: 1197
- 6e Gao K, Wu J. Org. Lett. 2008; 10: 2251
- 6f Bucher G, Mahajan AA, Schmittel M. J. Org. Chem. 2008; 73: 8815
- 6g Ye S, Yang X, Wu J. Chem. Commun. 2010; 46: 2590
- 6h Ye S, Wu J. Org. Lett. 2011; 13: 5980
- 7 Zhao J.-B, Clark DA. Org. Lett. 2012; 14: 1668
- 8 Zhang D.-H, Liu Z.-J, Yum EK, Larock RC. J. Org. Chem. 2007; 72: 251
- 9a Shimizu M, Hiyama T. Angew. Chem. Int. Ed. 2005; 44: 214
- 9b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
- 9c Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 9d Hagmann WK. J. Med. Chem. 2008; 51: 4359
- 10a Gassman PG, Ray JA, Wenthold PG, Mickelson JW. J. Org. Chem. 1991; 56: 5143
- 10b Jeong IH, Park YS, Kim MS, Song YS. J. Fluorine Chem. 2003; 120: 195
- 10c Hwang JH, Jung YH, Hong YY, Jeon SL, Jeong IH. J. Fluorine Chem. 2011; 132: 1227
- 11a Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
- 11b Lundgren RJ, Stradiotto M. Angew. Chem. Int. Ed. 2010; 49: 9322
- 11c Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475
- 11d Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
- 11e Roy S, Gregg BT, Gribble GW, Le VD, Roy S. Tetrahedron 2011; 67: 2161
- 12a Yoshida M, Yoshida T, Kobayashi M, Kamigata N. J. Chem. Soc., Perkin Trans. 1 1989; 909
- 12b Sawada H, Nakayama M. J. Fluorine Chem. 1990; 46: 423
- 12c Kino T, Nagase Y, Ohtsuka Y, Yamamoto K, Uraguchi D, Tokuhisa K, Yamakawa T. J. Fluorine Chem. 2010; 131: 98
- 12d Iqbal N, Choi S, Ko E, Cho EJ. Tetrahedron Lett. 2012; 53: 2005
- 13a Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
- 13b Uneyama K, Katagiri T, Amii H. Acc. Chem. Res. 2008; 41: 817
- 14a Dong S.-X, Zhang X.-G, Liu Q, Tang R.-Y, Zhong P, Li J.-H. Synthesis 2010; 1521
- 14b Li C.-L, Zhang X.-G, Tang R.-Y, Zhong P, Li J.-H. J. Org. Chem. 2010; 75: 7037
- 14c Sun L.-L, Liao Z.-Y, Tang R.-Y, Deng C.-L, Zhang X.-G. J. Org. Chem. 2012; 77: 2850
- 14d Shi S, Sun L.-L, Liao Z.-Y, Zhang X.-G. Synthesis 2012; 44: 966
- 15 This compound was prepared by the reaction of 2-bromo-benzaldehyde with CF3CCl3, followed by a Sonogashira reaction with phenylacetylene. All substrates 1 have almost the same Z/E ratio. See ref. 6e and: Fujita M, Hiyama T. Bull. Chem. Soc. Jpn. 1987; 60: 4377
- 16 D’Souza DM, Muschelknautz C, Rominger F, Müller TJ. J. Org. Lett. 2010; 12: 3364
For selected examples on the syntheses of indenes, see:
For selected examples on the syntheses of 1-methylene-indene, see:
For recent reviews, see:
For recent reviews, see: