ACCOUNT

Double Stabilization of Highly Strained Six-Membered Rings by Phosphonium and Transition Metal

  • Zhu Congqing ,
  • Cao Xiaoyu ,
  • Xia Haiping
Expand
  • College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005

Received date: 2013-01-31

  Revised date: 2013-03-21

  Online published: 2013-03-22

Supported by

Project supported by the National Basic Research Program of China (No. 2012CB821600), the National Natural Science Foundation of China (Nos. 21174115, 20925208) and the Program for Changjiang Scholars and Innovative Research Team in University.

Abstract

Cycloalkynes and cyclocumulenes have attracted considerable attention because they are key intermediates in organic synthesis. Stabilization of these highly active species remains a challenge for synthetic chemists. Recently, we found that phosphonium and transition metal replacement can double stabilize these species. Using this strategy, a series of highly strained six-membered rings with remarkable stability have been synthesized. Herein, the latest progress of our group is reviewed.

Cite this article

Zhu Congqing , Cao Xiaoyu , Xia Haiping . Double Stabilization of Highly Strained Six-Membered Rings by Phosphonium and Transition Metal[J]. Chinese Journal of Organic Chemistry, 2013 , 33(04) : 657 -662 . DOI: 10.6023/cjoc201301084

References

[1] Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.

[2] Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. Nature 2012, 490, 208.

[3] Goetz, A. E.; Garg, N. K. Nat. Chem. 2013, 5, 54.

[4] (a) Jaz, A.; Bradley, A. Z.; Burrell, R. C.; Li, W. H. H.; Daoust, K. J.; Bovee, L. B.; DiRico, K. J.; Johnson, R. P. J. Org. Chem. 2011, 76, 9320.
(b) Engels, B.; Schöneboom, J. C.; M黱ster, A. F.; Groetsch, S.; Christl, M. J. Am. Chem. Soc. 2002, 124, 287.
(c) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.

[5] (a) Smith, A. B. III; Kim, W.-S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6787.
(b) Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 17270.
(c) Carroll, F. I.; Robinson, T. P.; Brieaddy, L. E.; Atkinson, R. N.; Mascarella, S. W.; Damaj, M. I.; Martin, B. R.; Navarro, H. A. J. Med. Chem. 2007, 50, 6383.

[6] (a) Wen, T. B.; Zhou, Z. Y.; Jia, G. Angew. Chem., Int. Ed. 2001, 40, 1951.
(b) Suzuki, N.; Nishiura, M.; Wakatsuki, Y. Science 2002, 295, 660.
(c) Rosenthal, U. Angew. Chem., Int. Ed. 2004, 43, 3882.
(d) Jia, G. Coord. Chem. Rev. 2007, 251, 2167.
(e) Suzuki, N.; Hashizume, D. Coord. Chem. Rev. 2010, 254, 1307.

[7] Barrio, P.; Esteruelas, M. A.; Oñate, E. J. Am. Chem. Soc. 2004, 126, 1946.

[8] (a) Xia, H.; He, G.; Zhang, H.; Wen, T. B.; Sung, H. H. Y.; Williams, I. D.; Jia, G. J. Am. Chem. Soc. 2004, 126, 6862.
(b) Zhang, H.; Xia, H.; He, G.; Wen, T. B.; Gong, L.; Jia, G. Angew. Chem., Int. Ed. 2006, 45, 2920.
(c) Lin, R.; Zhang, H.; Li, S.; Wang, J.; Xia, H. Chem.-Eur. J. 2011, 17, 4223.

[9] Zhao, Q.; Gong, L.; Xu, C.; Zhu, J.; He, X.; Xia, H. Angew. Chem., Int. Ed. 2011, 50, 1354.

[10] Zhao, Q.; Zhu, J.; Huang, Z.-A.; Cao, X.-Y.; Xia, H. Chem.-Eur. J. 2012, 18, 11597.

[11] Wang, T.; Zhang, H.; Han, F.; Lin, R.; Lin, Z.; Xia, H. Angew. Chem., Int. Ed. 2012, 51, 9838.

[12] (a) Based on a search of the Cambridge Structural Database, 2011, CSD version 5.33.
(b) Bolaño, T.; Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2007, 26, 2037.
(c) Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2007, 26, 2129.

[13] (a) Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
(b) Peña, D.; P閞ez, D.; Guiti醤, E. Angew. Chem., Int. Ed. 2006, 45, 3579.
(c) Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140.
(d) Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520.

[14] (a) Ng, S. M.; Huang, X.; Wen, T. B.; Jia, G.; Lin, Z. Organometallics 2003, 22, 3898.
(b) Yang, S. Y.; Li, X. Y.; Huang, Y. Z. J. Organomet. Chem. 2002, 658, 9.

[15] (a) Chen, J.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. Angew. Chem., Int. Ed. 2011, 50, 10675.
(b) Chen, J.; Shi, C.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. Angew. Chem., Int. Ed. 2011, 50, 7295.
(c) He, G.; Zhu, J.; Hung, W. Y.; Wen, T. B.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. Angew. Chem., Int. Ed. 2007, 46, 9065.
(d) Wen, T. B.; Hung, W. Y.; Sung, H. H. Y.; Williams, I. D.; Jia, G. J. Am. Chem. Soc. 2005, 127, 2856.
(e) Wen, T. B.; Ng, S. M.; Hung, W. Y.; Zhou, Z. Y.; Lo, M. F.; Shek, L. Y.; Williams, I. D.; Lin, Z.; Jia, G. J. Am. Chem. Soc. 2003, 125, 884.

[16] Hung, W. Y.; Zhu, J.; Wen, T. B.; Yu, K. P.; Sung, H. H. Y.; Williams, I. D.; Lin, Z.; Jia, G. J. Am. Chem. Soc. 2006, 128, 13742.

[17] (a) Goetz, A. E.; Bronner, S. M.; Cisneros, J. D.; Melamed, J. M.; Paton, R. S.; Houk, K. N.; Garg, N. K. Angew. Chem., Int. Ed. 2012, 51, 2758.
(b) Jiang, L.; Yu, X.; Fang, B.; Wu, J. Org. Biomol. Chem. 2012, 10, 8102.
(c) Fang, Y.; Larock, R. C. Tetrahedron 2012, 68, 2819.
(d) Winkler, M.; Cakir, B.; Sander, W. J. Am. Chem. Soc. 2004, 126, 6135.

[18] (a) Weller, K. J.; Filippov, I.; Briggs, P. M.; Wigley, D. E. Organometallics 1998, 17, 322.
(b) Liu, B.; Wang, H.; Xie, H.; Zeng, B.; Chen, J.; Tao, J.; Wen, T.; Cao, Z.; Xia, H. Angew. Chem., Int. Ed. 2009, 48, 5430.

[19] (a) De Proft, F.; Geerlings, P. Phys. Chem. Chem. Phys. 2004, 6, 242.
(b) Mauksch, M.; Tsogoeva, S. B. Chem.-Eur. J. 2010, 16, 7843.

[20] (a) Jiao, H.; Schleyer, P. v. R.; Mo, Y.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1997, 119, 7075.
(b) Schleyer, P. V. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. V. E. J. Am. Chem. Soc. 1996, 118, 6317.
(c) Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. V. R. Chem. Rev. 2005, 105, 3842.

[21] Iron, M. A.; Lucassen, A. C. B.; Cohen, H.; van der Boom, M. E.; Martin, J. M. L. J. Am. Chem. Soc. 2004, 126, 11699.
Outlines

/