[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. |