Ruthenium-Catalyzed Cycloisomerization of 2,2′-Diethynyl- biphenyls Involving Cleavage of a Carbon-Carbon Triple Bond

Chemistry - A European Journal

Volumn 22, Issue 6, 2016, Pages 1941-1943

  Matsuda, Takanori ^a   Kato, Kotaro ^a   Goya, Tsuyoshi ^b   Shimada, Shingo ^a   Murakami, Masahiro ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

alkynes; cycloisomerization; phenanthrenes; ruthenium; vinylidene ligands

Indexed keywords

ANTHRACENE; BUTENES; CATALYSIS; ISOMERIZATION; RUTHENIUM; RUTHENIUM COMPOUNDS;

ALKYNES; CARBON-CARBON DOUBLE BONDS; CARBON-CARBON TRIPLE BONDS; CYCLOISOMERIZATION REACTIONS; CYCLOISOMERIZATIONS; PHENANTHRENES; VINYLIDENE COMPLEXES; VINYLIDENE LIGANDS;

CARBON;

EID: 84970883639     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201504937     Document Type: Article

References (50)

1. M. I. Bruce, Chem. Rev. 1991, 91, 197;
2. J. P. Selegue, Coord. Chem. Rev. 2004, 248, 1543;
3. H. Werner, Coord. Chem. Rev. 2004, 248, 1693;
4. Y. Wakatsuki, J. Organomet. Chem. 2004, 689, 4092;
5. Metal Vinylidenes and Allenylidenes in Catalysis (Eds.:, C. Bruneau, P. Dixneuf,), Wiley-VCH, Weinheim (Germany), 2008;
6. J. M. Lynam, Chem. Eur. J. 2010, 16, 8238.
7. C. Bruneau, P. H. Dixneuf, Acc. Chem. Res. 1999, 32, 311;
8. H. Katayama, F. Ozawa, Coord. Chem. Rev. 2004, 248, 1703;
9. C. Bruneau, P. H. Dixneuf, Angew. Chem. Int. Ed. 2006, 45, 2176;
10. Angew. Chem. 2006, 118, 2232;
11. Angew. Chem. 2006, 118, 2232;
12. J. A. Varela, C. Saá, Chem. Eur. J. 2006, 12, 6450;
13. K. Ohe, Bull. Korean Chem. Soc. 2007, 28, 2153;
14. B. M. Trost, A. McClory, Chem. Asian J. 2008, 3, 164;
15. R.-S. Liu, Synlett 2008, 801;
16. J. A. Varela, C. González-Rodríguez, C. Saá, Top. Organomet. Chem. 2014, 48, 237.
17. A. S. Gamble, K. R. Birdwhistell, J. L. Templeton, Organometallics 1988, 7, 1046;
18. D. Bauer, P. Härter, E. Herdtweck, J. Chem. Soc. Chem. Commun. 1991, 829;
19. H. Fischer, O. Podschadly, A. Früh, C. Troll, R. Stumpf, A. Schlageter, Chem. Ber. 1992, 125, 2667;
20. H. Fischer, H.-P. Volkland, A. Früh, R. Stumpf, J. Organomet. Chem. 1995, 491, 267;
21. W. Weng, T. Bartik, M. T. Johnson, A. M. Arif, J. A. Gladysz, Organometallics 1995, 14, 889;
22. H. Fischer, F. Leroux, G. Roth, R. Stumpf, Organometallics 1996, 15, 3723;
23. H. Fischer, O. Podschadly, G. Roth, S. Herminghaus, S. Klewitz, J. Heck, S. Houbrechts, T. Meyer, J. Organomet. Chem. 1997, 541, 321;
24. F. Leroux, R. Stumpf, H. Fischer, Eur. J. Inorg. Chem. 1998, 1225;
25. M. A. Jiménez Tenorio, M. Jiménez Tenorio, M. C. Puerta, P. Valerga, Organometallics 2000, 19, 1333;
26. P. Alvarez, E. Lastra, J. Gimeno, M. Bassetti, L. R. Falvello, J. Am. Chem. Soc. 2003, 125, 2386;
27. J. Díez, M. P. Gamasa, J. Gimeno, E. Lastra, A. Villar, Organometallics 2005, 24, 1410;
28. Y.-S. Yen, Y.-C. Lin, S.-L. Huang, Y.-H. Liu, H.-L. Sung, Y. Wang, J. Am. Chem. Soc. 2005, 127, 18037;
29. C.-W. Cheng, Y.-C. Kuo, S.-H. Chang, Y.-C. Lin, Y.-H. Liu, Y. Wang, J. Am. Chem. Soc. 2007, 129, 14974;
30. L.-H. Chang, C.-W. Yeh, H.-W. Ma, S.-Y. Liu, Y.-C. Lin, Y. Wang, Y.-H. Liu, Organometallics 2010, 29, 1092.
31. T. Matsuda, T. Moriya, T. Goya, M. Murakami, Chem. Lett. 2011, 40, 40;
32. D. B. Walker, J. Howgego, A. P. Davis, Synthesis 2010, 3686;
33. M. M. Machuy, C. Würtele, P. R. Schreiner, Synthesis 2012, 44, 1405.
34. T. Matsuda, T. Goya, L. Liu, Y. Sakurai, S. Watanuki, N. Ishida, M. Murakami, Angew. Chem. Int. Ed. 2013, 52, 6492;
35. Angew. Chem. 2013, 125, 6620.
36. W. Baidossi, H. Schumann, J. Blum, Tetrahedron 1996, 52, 8349;
37. T. Suzuki, S. Tanaka, H. Higuchi, H. Kawai, K. Fujiwara, Tetrahedron Lett. 2004, 45, 8563;
38. A. McIver, D. D. Young, A. Deiters, Chem. Commun. 2008, 4750;
39. H. Tsuji, I. Tanaka, K. Endo, K. Yamagata, M. Nakamura, E. Nakamura, Org. Lett. 2009, 11, 1845;
40. T. Shibata, T. Uchiyama, Y. Yoshinami, S. Takayasu, K. Tsuchikama, K. Endo, Chem. Commun. 2012, 48, 1311;
41. Y. Sawada, S. Furumi, A. Takai, M. Takeuchi, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2012, 134, 4080;
42. K. Murayama, Y. Sawada, K. Noguchi, K. Tanaka, J. Org. Chem. 2013, 78, 6202;
43. A. Jančařík, J. Rybáček, K. Cocq, J. V. Chocholoušová, J. Vacek, R. Pohl, L. Bednárová, P. Fiedler, I. Císařová, I. G. Stará, I. Starý, Angew. Chem. Int. Ed. 2013, 52, 9970;
44. Angew. Chem. 2013, 125, 10154;
45. K. Murayama, Y. Oike, S. Furumi, M. Takeuchi, K. Noguchi, K. Tanaka, Eur. J. Org. Chem. 2015, 1409.
46. H.-C. Shen, J.-M. Tang, H.-K. Chang, C.-W. Yang, R.-S. Liu, J. Org. Chem. 2005, 70, 10113;
47. C. A. Merlic, M. E. Pauly, J. Am. Chem. Soc. 1996, 118, 11319;
48. P. M. Donovan, L. T. Scott, J. Am. Chem. Soc. 2004, 126, 3108;
49. K. Maeyama, N. Iwasawa, J. Org. Chem. 1999, 64, 1344.
50. M. Sarobe, R. van Heerbeek, L. W. Jenneskens, J. W. Zwikker, Liebigs Ann. 1997, 2499.