New Synthesis of Dibenzofulvenes by Palladium-Catalyzed Double Cross-Coupling Reactions
Masaki Shimizu A C , Ikuhiro Nagao A , Shin-ichi Kiyomoto A and Tamejiro Hiyama A B
+ Author Affiliations
- Author Affiliations
A Department of Materials Chemistry, Graduate School of Engineering, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
B Current address: Research & Development Initiative, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
C Corresponding author. Email: m.shimizu@hs2.ecs.kyoto-u.ac.jp
Australian Journal of Chemistry 65(9) 1277-1284 https://doi.org/10.1071/CH12060
Submitted: 31 January 2012 Accepted: 22 February 2012 Published: 13 April 2012
Abstract
Palladium-catalyzed double cross-coupling reactions of 1,1-bis(pinacolato)borylalk-1-enes with 2,2′-dibromobiaryls and of 9-stannafluorenes with 1,1-dibromoalk-1-enes have been demonstrated to serve as new synthetic methods for dibenzofulvenes.
References
[1] (a) H. Tong, Y. Dong, M. Häußler, J. W. Y. Lam, H. H. Y. Sung, I. D. Williams, J. Sun, B. Z. Tang, Chem. Commun. 2006, 1133.| Crossref | GoogleScholarGoogle Scholar |
(b) H. Tong, Y. Dong, Y. Hong, M. Haussier, J. W. Y. Lam, H. H. Y. Sung, X. Yu, J. Sun, I. D. Williams, H. S. Kwok, B. Z. Tang, J. Phys. Chem. C 2007, 111, 2287.
| Crossref | GoogleScholarGoogle Scholar |
(c) X. Luo, J. Li, C. Li, L. Heng, Y. Q. Dong, Z. Liu, Z. Bo, B. Z. Tang, Adv. Mater. 2011, 23, 3261.
| Crossref | GoogleScholarGoogle Scholar |
(d) F. G. Brunetti, X. Gong, M. Tong, A. J. Heeger, F. Wudl, Angew. Chem. Int. Ed. 2010, 49, 532.
| Crossref | GoogleScholarGoogle Scholar |
(e) F. G. Brunetti, A. Varotto, N. A. Batara, F. Wudl, Chem.–Eur. J. 2011, 17, 8604.
| Crossref | GoogleScholarGoogle Scholar |
(f) H. Usta, A. Facchetti, T. J. Marks, J. Am. Chem. Soc. 2008, 130, 8580.
| Crossref | GoogleScholarGoogle Scholar |
(g) H. Usta, A. Facchetti, T. J. Marks, Org. Lett. 2008, 10, 1385.
| Crossref | GoogleScholarGoogle Scholar |
(h) H. Usta, C. Risko, Z. Wang, H. Huang, M. K. Deliomeroglu, A. Zhukhovitskiy, A. Facchetti, T. J. Marks, J. Am. Chem. Soc. 2009, 131, 5586.
| Crossref | GoogleScholarGoogle Scholar |
(i) J. Vicario, M. Walko, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 5127.
| Crossref | GoogleScholarGoogle Scholar |
(j) R. Eelkema, B. L. Feringa, Chem. Asian J. 2006, 1, 367.
| Crossref | GoogleScholarGoogle Scholar |
(k) D. Pijper, B. L. Feringa, Angew. Chem. Int. Ed. 2007, 46, 3693.
| Crossref | GoogleScholarGoogle Scholar |
(l) T. L. Andrew, J. R. Cox, T. M. Swager, Org. Lett. 2010, 12, 5302.
| Crossref | GoogleScholarGoogle Scholar |
[2] M. L. T. M. B. Franco, B. J. Herold, J. C. Evans, C. C. Rowlands, J. Chem. Soc., Perkin Trans. 2 1988, 443.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXnsFaj&md5=923ee91d40c210ef7237732568a6faacCAS |
[3] M. Banerjee, S. J. Emond, S. V. Lindeman, R. Rathore, J. Org. Chem. 2007, 72, 8054.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVGmtbvF&md5=848bce285500ba407be0e0fcb8acdeecCAS |
[4] (a) N. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 5636.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjslahtrs%3D&md5=7b1753c54351315a956bc367844b5466CAS |
(b) N. Chernyak, V. Gevorgyan, Adv. Synth. Catal. 2009, 351, 1101.
| Crossref | GoogleScholarGoogle Scholar |
(c) S. A. Kandil, R. E. Dessy, J. Am. Chem. Soc. 1966, 88, 3027.See also
| Crossref | GoogleScholarGoogle Scholar |
[5] (a) Q. Tian, R. C. Larock, Org. Lett. 2000, 2, 3329.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXmslGis7w%3D&md5=13da806085d1a5be542597ec5d0b56b0CAS |
(b) R. C. Larock, Q. Tian, J. Org. Chem. 2001, 66, 7372.
| Crossref | GoogleScholarGoogle Scholar |
(c) T. Morishita, H. Yoshida, J. Ohshita, Chem. Commun. 2010, 46, 640.See also
| Crossref | GoogleScholarGoogle Scholar |
[6] V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Chem.–Eur. J. 2010, 16, 1436.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVGqu78%3D&md5=55761aac8db36377528fdc6166a316b0CAS |
[7] (a) C. V. Ramana, B. K. Kishore Reddy, C. Nageswara Reddy, R. G. Gonnade, M. K. Gurjar, Synlett 2007, 127.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1Squr8%3D&md5=e59c0f8599baaa1305622d217a801188CAS |
(b) S. Paul, T. Gorai, A. Koley, J. K. Ray, Tetrahedron Lett. 2011, 52, 4051.
| Crossref | GoogleScholarGoogle Scholar |
[8] (a) M. Shimizu, I. Nagao, Y. Tomioka, T. Hiyama, Angew. Chem. Int. Ed. 2008, 47, 8096.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Olu7fO&md5=c28732d4a5157304f5af5a674a49cce8CAS |
(b) M. Shimizu, Y. Tomioka, I. Nagao, T. Hiyama, Synlett 2009, 3147.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Shimizu, I. Nagao, Y. Tomioka, T. Kadowaki, T. Hiyama, Tetrahedron 2011, 67, 8014.
| Crossref | GoogleScholarGoogle Scholar |
(d) I. Nagao, M. Shimizu, T. Hiyama, Angew. Chem. Int. Ed. 2009, 48, 7573.
| Crossref | GoogleScholarGoogle Scholar |
[9] (a) T. Hata, H. Kitagawa, H. Masai, T. Kurahashi, M. Shimizu, T. Hiyama, Angew. Chem. Int. Ed. 2001, 40, 790.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhs12qtbo%3D&md5=668a2db70605c24892b869eb8b37a94aCAS |
(b) T. Kurahashi, T. Hata, H. Masai, H. Kitagawa, M. Shimizu, T. Hiyama, Tetrahedron 2002, 58, 6381.
| Crossref | GoogleScholarGoogle Scholar |
(c) M. Shimizu, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc. 2005, 127, 1250.
| Crossref | GoogleScholarGoogle Scholar |
[10] In ref. [8d], two examples of the annulation using 7 and 1,1-dibromoalk-1-enes were preliminarily reported.
[11] To the best of our knowledge, this is the first synthesis of dinaphthofulvenes of type 4e.