Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethyl­indenes

Wen-Ying Wang; Lei-Lei Sun; Chen-Liang Deng; Ri-Yuan Tang; Xing-Guo Zhang

doi:10.1055/s-0032-1317849

Synthesis, Table of Contents

Synthesis 2013; 45(1): 118-126
DOI: 10.1055/s-0032-1317849

paper

Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethylindenes

Authors

Wen-Ying Wang

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China Fax: +86(577)86689615 Email: zxg@wzu.edu.cn
Lei-Lei Sun

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China Fax: +86(577)86689615 Email: zxg@wzu.edu.cn
Chen-Liang Deng

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China Fax: +86(577)86689615 Email: zxg@wzu.edu.cn
Ri-Yuan Tang

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China Fax: +86(577)86689615 Email: zxg@wzu.edu.cn
Xing-Guo Zhang*

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China Fax: +86(577)86689615 Email: zxg@wzu.edu.cn

Abstract

All articles of this category

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.

Key words

indene - palladium - trifluoromethyl - carbocyclization - Suzuki coupling

Full Text

References

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

For selected examples on the syntheses of indenes, see:

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

For selected examples on the syntheses of 1-methylene-indene, see:

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

For recent reviews, see:

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

For recent reviews, see:

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

17a Sköld C, Kleimark J, Trejos A, Odell LR, Lill SO. N, Norrby P.-O, Larhed M. Chem. Eur. J. 2012; 18: 4714
17b Trejos A, Fardost A, Yahiaoui S, Larhed M. Chem. Commun. 2009; 7587

Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethyl­indenes

Authors

Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethylindenes