Chinese Journal of Organic Chemistry >
Recent Advances in Aryne Double Bond Insertion
Received date: 2014-11-26
Revised date: 2014-12-15
Online published: 2015-01-09
Supported by
Project supported by National Natural Science Foundation of China (No. 21002021) and the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 13HASTIT010).
Aryne double bond insertion generates an ortho-quinomethide-typed intermediate, which, like aryne itself, is one of the most important reactive intermediates in organic reactions. This review summarizes recent advances in this field and the potential applications in synthetic organic chemistry, with a focus on the reaction mechanism, as well as the structure and reactivity of the ortho-quinomethide intermediates.
Wu Chunrui , Yang Yupo , Shi Feng . Recent Advances in Aryne Double Bond Insertion[J]. Chinese Journal of Organic Chemistry, 2015 , 35(4) : 770 -780 . DOI: 10.6023/cjoc201411041
[1] For reviews, see:
(a) Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701.
(b) Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
(c) Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140.
(d) Wu, C.-R.; Shi, F. Asian J. Org. Chem. 2013, 2, 116.
(e) Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191.
(f) Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766.
(g) Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550.
[2] Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 12, 1211.
[3] For reviews of aryne insertion into s-bonds, see:
(a) Pena, D.; Perez, D.; Guitian, E. Angew. Chem., Int. Ed. 2006, 45, 3579.
(b) Yoshida, H.; Ohshita, J.; Kunai, A. Bull. Chem. Soc. Jpn. 2010, 83, 199.
[4] For reviews of o-quinomethides and related intermediates, see:
(a) Zheng, R.-S.; Zhu, S.-F. Chin. J. Org. Chem. 2014, 34, 1322 (in Chinese).
(郑若山, 祝诗发, 有机化学, 2014, 34, 1322.)
(b) Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199.
(c) Collier, S. J.; Storr, R. C. In Progress in Heterocyclic Chemistry, Vol. 10, Eds.: Gribble, G. W.; Gilchrist, T. L., Elsevier Science, Oxford, UK, 1998, pp. 25～48.
[5] Crews, P.; Beard, J. J. Org. Chem. 1973, 38, 522.
[6] Caubère, P. Top. Curr. Chem. 1978, 73, 49.
[7] (a) Hamura, T.; Ibusuki, Y.; Sato, K.; Matsumoto, T.; Osamura, Y.; Suzuki, K. Org. Lett. 2013, 15, 3551.
(b) Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 3534.
(c) Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Siegel, J. S.; Baldridge, K. K.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 10032.
(d) Hamura, T.; Arisawa, T.; Matsumoto, T.; Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 6842.
[8] (a) Gingrich, H. L.; Huang, Q.; Morales, A. L.; Jones, M. J. Org. Chem. 1992, 57, 3803.
(b) Heaney, H.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1974, 2693.
[9] Feltenberger, J. B.; Hayashi, R.; Tang, Y.; Babiash, E. S. C.; Hsung, R. P. Org. Lett. 2009, 11, 3666.
[10] Ma, Z.-X.; Feltenberger, J. B.; Hsung, R. P. Org. Lett. 2012, 14, 2742.
[11] Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029.
[12] Li, R.; Wang, X.-M.; Wei, Z.-B.; Wu, C.-R.; Shi, F. Org. Lett. 2013, 15, 4366.
[13] Li, R.; Tang, H.-R.; Fu, H.-X.; Wang, X.-M.; Wu, C.-R.; Wu, C.; Shi, F. J. Org. Chem. 2014, 79, 1344. [14] Nakayama, J.; Midorikawa, H.; Yoshida, M. Bull. Chem. Soc. Jpn. 1975, 48, 1063.
[15] Aly, A. A.; Mohamed, N. K.; Hassan, A. A.; Mourad, A.-F. E. Tetrahedron 1999, 55, 1111.
[16] Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040.
[17] Zhou, Y.; Chi, Y.; Zhao, F.; Zhang, W.-X.; Xi, Z.-F. Chem. Eur. J. 2014, 20, 2463.
[18] Nair, V.; Kim, K. H. J. Org. Chem. 1975, 40, 3784.
[19] Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2004, 6, 4049.
[20] Yoshioka, E.; Kohtani, S.; Miyabe, H. Org. Lett. 2010, 12, 1956.
[21] Yoshioka, E.; Miyabe, H. Tetrahedron 2012, 68, 179.
[22] Yoshioka, E.; Kohtani, S.; Miyabe, H. Angew. Chem., Int. Ed. 2011, 50, 6638.
[23] (a) Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340.
(b) Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Commun. 2005, 3292.
[24] (a) Yoshioka, E.; Tanaka, H.; Kohtani, S.; Miyabe, H. Org. Lett. 2013, 15, 3938.
(b) Yoshioka, E.; Kohtani, S.; Miyabe, H. Molecules 2014, 19, 863.
[25] Zhou, C.; Wang, J.; Jin, J.-S.; Lu, P.; Wang Y.-G. Eur. J. Org. Chem. 2014, 1832.
[26] Yoshioka, E.; Tamenaga, H.; Miyabe, H. Tetrahedron Lett. 2014, 55, 1402.
[27] Zhang, T.-X.; Huang, X.; Wu, L.-L. Eur. J. Org. Chem. 2012, 3507.
[28] Stokes, S.; Bekkam, M.; Rupp, M.; Mead, K. T. Synlett 2012, 23, 389.
[29] Zbiral, E. Tetrahedron Lett. 1964, 5, 3963.
[30] Alajarin, M.; Lopez-Leonardo, C.; Raja, R.; Orenes, R.-A. Org. Lett. 2011, 13, 5668.
[31] Lopez-Leonardo, C.; Raja, R.; López-Ortiz, F.; águila-Sánchez, M. A. D.; Alajarin, M. Eur. J. Org. Chem. 2014, 1084.
[32] It is possible that the ring opening of these benzannulated 4-membered ring intermediates is not retro-4p electrocyclization, but a simple heterolytic P—X bond cleavage, due to the structure and orientation of pentavalent phosphorous atoms.
Biswas, K.; Greaney, M. F. Org. Lett. 2011, 13, 4946.
[33] Liu, F.-L.; Chen, J.-R.; Zou, Y.-Q.; Wei, Q.; Xiao, W.-J. Org. Lett. 2014, 16, 3768.
[34] Chakrabarty, S.; Chatterjee, I.; Tebben, L.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 1.
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