Palladium-catalyzed tandem carbocyclization-suzuki coupling reactions of trifluoromethyl-containing building blocks leading to 2-trifluoromethylindenes

Synthesis (Germany)

Volumn 45, Issue 1, 2013, Pages 118-126

  Wang, Wen Ying ^a   Sun, Lei Lei ^a   Deng, Chen Liang ^a   Tang, Ri Yuan ^a   Zhang, Xing Guo ^a  

^a WENZHOU UNIVERSITY   (China)

Author keywords

carbocyclization; indene; palladium; Suzuki coupling; trifluoromethyl

Indexed keywords

ARYLBORONIC ACIDS; BUILDING BLOCKES; CARBOCYCLIZATION; COUPLING REACTION; INDENE; PALLADIUM ACETATE; PALLADIUM-CATALYZED; SUZUKI COUPLINGS; TRIFLUOROMETHYL;

ORGANIC SOLVENTS; PALLADIUM; PALLADIUM COMPOUNDS; PHOSPHORUS; PHOSPHORUS COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS; POTASSIUM; TOLUENE;

CATALYSIS;

1 (DIPHENYLMETHYLENE) 2 (TRIFLUOROMETHYL) 1H INDENE; 1 (DIPHENYLMETHYLENE) 5 METHOXY 2 (TRIFLUOROMETHYL) 1H INDENE; 1 (DIPHENYLMETHYLENE) 6 FLUORO 2 (TRIFLUOROMETHYL) 1H INDENE; 1 (DIPHENYLMETHYLENE) 6 METHYL 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [(2 METHOXYPHENYL)(PHENYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [(3 NITROPHENYL)(PHENYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [(4 CHLOROPHENYL)(PHENYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [(4 FLUOROPHENYL)(PHENYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [(4 METHOXYPHENYL)(PHENYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [(4 NITROPHENYL)(PHENYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [4 [PHENYL [2 (TRIFLUOROMETHYL) 1H INDEN 1 YLIDENE]METHYL]PHENYL]ETHANONE; 1 [PHENYL (3 TOLYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [PHENYL (4 TOLYL)METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 1 [PHENYL [2 (TRIFLUOROMETHYL) 1H INDEN 1 YLIDENE]METHYL]NAPHTHALENE; 1 [PHENYL [4 (TRIFLUOROMETHYL)PHENYL]METHYLENE] 2 (TRIFLUOROMETHYL) 1H INDENE; 2 TRIFLUOROMETHY INDENE; 4 [PHENYL [2 (TRIFLUOROMETHYL) 1H INDEN 1 YLIDENE]METHYL]BENZONITRILE; ALKYLBENZENE; BORONIC ACID DERIVATIVE; INDENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBOCYCLIZATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; HIGH RESOLUTION MELTING ANALYSIS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 84871620637     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1317849     Document Type: Article

References (48)

1. Majetich G., Shimkus J. M. J. Nat. Prod.: 2010; 73 284
2. Lee B. H., Choi Y. L., Shin S., Heo J. N. J. Org. Chem.: 2011; 76 6611
3. Gao H., Katzenellenbogen J. A., Garg R., Hansch C. Chem. Rev.: 1999; 99 723
4. Korte A., Legros J., Bolm C. Synlett: 2004; 2397
5. Alcalde E., Mesquida N., López-Pérez S., Frigola J., Mercè R. J. Med. Chem.: 2009; 52 675
6. Solomak T., Stacko P., Veetil A. T., Pospisil T., Klan P. J. Org. Chem.: 2010; 75 7300
7. Akbulut U., Khurshid A., Hacioglu B., Toppare L. Polymer: 1990; 31 1343
8. Barbera J., Rakitin O. A., Ros M. B., Torroba T. Angew. Chem. Int. Ed.: 1998; 37 296
9. Yang J., Lakshmikantham M. V., Cava M. P., Lorcy D., Bethelot J. R. J. Org. Chem.: 2000; 65 6739
10. Alt H. G., Köppl A. Chem. Rev.: 2000; 100 1205
11. Kim D. H., Lee J. A., Lee B. Y., Chung Y. K. J. Organomet. Chem.: 2005; 690 1822
12. Izmer V. V., Lebedev A. Y., Nikulin M. V., Ryabov A. N., Asachenko A. F., Lygin A. V., Sorokin D. A., Voskoboynikov A. Z. Organometallics: 2006; 25 1217
13. Wang S., Zhu Y., Wang Y., Lu P. Org. Lett.: 2009; 11 2615
14. Ye S., Gao K., Zhou H., Yang X., Wu J. Chem. Commun.: 2009; 5406
15. Tran D. N., Cramer N. Angew. Chem. Int. Ed.: 2011; 50 11098
16. Zhou F., Han X., Lu X. J. Org. Chem.: 2011; 76 1491
17. Schreiner P. R., Prall M., Lutz V. Angew. Chem. Int. Ed.: 2003; 42 5757
18. Bekele T., Christian C. F., Lipton M. A., Singleton D. A. J. Am. Chem. Soc.: 2005; 127 9216
19. Furuta T., Asakawa T., Iinuma M., Fujii S., Tanaka K., Kan T. Chem. Commun.: 2006; 3648
20. Rahman S. M. A, Sonoda M., Ono M., Miki K., Tobe Y. Org. Lett.: 2006; 8 1197
21. Gao K., Wu J. Org. Lett.: 2008; 10 2251
22. Bucher G., Mahajan A. A., Schmittel M. J. Org. Chem.: 2008; 73 8815
23. Ye S., Yang X., Wu J. Chem. Commun.: 2010; 46 2590
24. Ye S., Wu J. Org. Lett.: 2011; 13 5980
25. Shimizu M., Hiyama T. Angew. Chem. Int. Ed.: 2005; 44 214
26. Müller K., Faeh C., Diederich F. Science: 2007; 317 1881
27. Purser S., Moore P. R., Swallow S., Gouverneur V. Chem. Soc. Rev.: 2008; 37 320
28. Hagmann W. K. J. Med. Chem.: 2008; 51 4359
29. Gassman P. G., Ray J. A., Wenthold P. G., Mickelson J. W. J. Org. Chem.: 1991; 56 5143
30. Jeong I. H., Park Y. S., Kim M. S., Song Y. S. J. Fluorine Chem.: 2003; 120 195
31. Hwang J. H., Jung Y. H., Hong Y. Y., Jeon S. L., Jeong I. H. J. Fluorine Chem.: 2011; 132 1227
32. Schlosser M. Angew. Chem. Int. Ed.: 2006; 45 5432
33. Lundgren R. J., Stradiotto M. Angew. Chem. Int. Ed.: 2010; 49 9322
34. Tomashenko O. A., Grushin V. V. Chem. Rev.: 2011; 111 4475
35. Furuya T., Kamlet A. S., Ritter T. Nature: 2011; 473 470
36. Roy S., Gregg B. T., Gribble G. W., Le V. D., Roy S. Tetrahedron: 2011; 67 2161
37. Yoshida M., Yoshida T., Kobayashi M., Kamigata N. J. Chem. Soc., Perkin Trans. 1: 1989; 909
38. Sawada H., Nakayama M. J. Fluorine Chem.: 1990; 46 423
39. Kino T., Nagase Y., Ohtsuka Y., Yamamoto K., Uraguchi D., Tokuhisa K., Yamakawa T. J. Fluorine Chem.: 2010; 131 98
40. Iqbal N., Choi S., Ko E., Cho E. J. Tetrahedron Lett.: 2012; 53 2005
41. Schlosser M. Angew. Chem. Int. Ed.: 2006; 45 5432
42. Uneyama K., Katagiri T., Amii H. Acc. Chem. Res.: 2008; 41 817
43. Dong S.-X, Zhang X.-G, Liu Q., Tang R.-Y, Zhong P., Li J.-H. Synthesis: 2010; 1521
44. Li C.-L, Zhang X.-G, Tang R.-Y, Zhong P., Li J.-H. J. Org. Chem.: 2010; 75 7037
45. Sun L.-L, Liao Z.-Y, Tang R.-Y, Deng C.-L, Zhang X.-G. J. Org. Chem.: 2012; 77 2850
46. Shi S., Sun L.-L, Liao Z.-Y, Zhang X.-G. Synthesis: 2012; 44 966
47. Sköld C., Kleimark J., Trejos A., Odell L. R., Lill S. O. N, Norrby P.-O, Larhed M. Chem. Eur. J.: 2012; 18 4714
48. Trejos A., Fardost A., Yahiaoui S., Larhed M. Chem. Commun.: 2009; 7587