N-Heterocycle Synthesis via Gold-Catalyzed Intermolecular Nitrene Transfer Reactions of Alkynes
- Corresponding author: Chen Gui, chengui@fjirsm.ac.cn Huang Xueliang, huangxl@fjirsm.ac.cn
Citation:
Liao Yun, Zhu Lei, Yu Yinghua, Chen Gui, Huang Xueliang. N-Heterocycle Synthesis via Gold-Catalyzed Intermolecular Nitrene Transfer Reactions of Alkynes[J]. Chinese Journal of Organic Chemistry,
;2017, 37(11): 2785-2799.
doi:
10.6023/cjoc201708021
(a) Pozharskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R. Heterocycles in Life and Society, Wiley, New York, 1997.
(b) Katritzky, A. R. Handbook of Heterocyclic Chemistry, Per-gamon Press, Oxford, 1985.
(c) Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Chem. Rev. 2004, 104, 2777.
Related reviews, see:(a) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
(b) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
(c) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
(d) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.
(e) Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208.
(f) Hashmi, A. S. K. Angew. Chem., Int. Ed.2010, 49, 5232.
(g) Xiao, J.; Li, X. Angew. Chem., Int. Ed. 2011, 50, 7226.
(h) Friend, C. M.; Hashmi, A. S. K. Acc. Chem. Res. 2014, 47, 729.
(i) Zhang, L. Acc. Chem. Res. 2014, 47, 877.
(j) Yeom, H.-S.; Shin, S. Acc. Chem. Res. 2014, 47, 966.
(k) Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115, 9028.
(l) Qian, D.; Zhang, J. Chem. Soc. Rev. 2015, 44, 677.
(m) Davies, P. W.; Garzûn, M. Asian J. Org. Chem. 2015, 4, 694.
(n) Huple, D. B.; Ghorpade, S.; Liu, R.-S. Adv. Synth. Catal. 2016, 358, 1348.
(o) Pan, F.; Shu, C.; Ye, L.-W. Org. Biomol. Chem. 2016, 14, 9456.
(p) Shu, C.; Li, L.; Tan, T.-D.; Yuan, D.-Q.; Ye, L.-W. Sci. Bull. 2017, 62, 352.
Recent related reviews, see:(a) Davies, P. W.; Garzûn, M. Asian J. Org. Chem. 2015, 4, 694.
(b) Song, X.-R.; Qiu, Y.-F.; Liu, X.-Y.; Liang, Y.-M. Org. Bio-mol. Chem. 2016, 14, 11317.
(a) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
(b) Huo, Z.; Yamamoto, Y. Tetrahedron Lett. 2009, 50, 3651.
(c) Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354.
(d) Lu, B.; Luo, Y.; Liu, L.; Ye, L.; Wang, Y.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 8358.
(e) Yan, Z.-Y.; Xiao, Y.; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 8624.
(f) Xiao, Y.; Zhang, L. Org. Lett. 2012, 14, 4662.
(g) Gronnier, C.; Boissonnat G.; Gagosz, F. Org. Lett. 2013, 15, 4234.
(h) Prechter, A.; Henrion, G.; Bel, P. F.; Gagosz, F. Angew. Chem., Int. Ed. 2014, 53, 4959.
(i) Shen, C.-H.; Pan, Y.; Yu, Y.-F.; Wang, Z.-S.; He, W.; Li, T.; Ye, L.-W. J. Organomet. Chem. 2015, 795, 63.
(j) Li, N.; Wang, T. Y.; Gong, L. Z.; Zhang, L. Chem. Eur. J. 2015, 21, 3585.
(k) Pan, Y.; Chen, G.-W.; Shen, C.-H.; He, W.; Ye, L.-W. Org. Chem. Front. 2016, 3, 491.
(l) Li, N.; Lian, X. L.; Li, Y. H.; Wang, T. Y.; Han, Z. Y.; Zhang, L.; Gong, L. Z. Org. Lett. 2016, 18, 4178.
(m) Lonca, G. H.; Tejo, C.; Chan, H. L.; Chiba, S.; Gagosz, F. Chem. Commun. 2017, 53, 736.
(n) Zhang, X.-X.; Sun, X.-P.; Fan, H.; Li, P.; Lyu, C.; Rao, W.-D. Eur. J. Org. Chem. 2016, 25, 4265.
(o) Zhang, X.-X.; Sun, X.-P.; Fan, H.; Lyu, C.; Li, P.; Zhang, H.-F.; Rao, W.-D. RSC Adv. 2016, 6, 56319.
(p) Zhang, X.-X; Li, P.; Lyu, C.; Yong, W.-X.; Li, J.; Zhu, X.-B.; Rao, W.-D. Org. Biomol. Chem. 2017, 15, 6080.
(q) González, J.; Santamaría, J.; Suárez-Sobrino, Á. L.; Ballesteros, A. Adv. Synth. Catal. 2016, 358, 1398.
Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738.
doi: 10.1021/ol2002607
(a) Davies, P. W.; Cremonesi, A.; Dumitrescu, L. Angew. Chem., Int. Ed. 2011, 50, 8931.
(b) Gillie, A. D.; Reddy, R. J.; Davies, P. W. Adv. Synth. Catal. 2016, 358, 226.
(a) Chatzopoulou, E.; Davies, P. W. Chem. Commun. 2013, 49, 8617.
(b) Garzûn, M.; Davies, P. W. Org. Lett. 2014, 16, 4850.
Reddy, R. J.; Ball-Jones, M. P.; Davies, P. W. Angew. Chem., Int. Ed. 2017, 56, 13310..
doi: 10.1002/anie.201706850
Sahani, R. L.; Liu, R.-S. Angew. Chem., Int. Ed. 2017, 56, 1026.
doi: 10.1002/anie.201610665
(a) Jin, H.; Huang, L.; Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 794.
(b) Jin, H.; Tian, B.; Song, X.; Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 12688.
(c) Sahani, L.-R.; Liu, R.-S. Angew. Chem., Int. Ed. 2017, 56, 12736.
Chen, M.; Sun, N.; Chen, H.-Y.; Liu, Y.-H. Chem. Commun. 2016, 52, 6324.
doi: 10.1039/C6CC02776H
Zhao, Y.-Y.; Hu, Y.-C.; Wang, C.-X.; Li, X.-C.; Wan, B.-S. J. Org. Chem. 2017, 82, 3935.
doi: 10.1021/acs.joc.7b00076
Xu, W.; Wang, G.-N.; Sun, N.; Liu, Y.-H. Org. Lett. 2017, 19, 3307.
doi: 10.1021/acs.orglett.7b01469
Zeng, Z.-Y.; Jin, H.-M.; Xie, J.; Tian, B.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Org. Lett. 2017, 19, 1020.
doi: 10.1021/acs.orglett.7b00001
Zeng, Z.; Jin, H.; Song, X.; Wang, Q.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Chem. Commun. 2017, 53, 4304.
doi: 10.1039/C7CC00789B
Zhu, L.; Yu, Y.; Mao, Z.; Huang, X. Org. Lett. 2015, 17, 30.
doi: 10.1021/ol503172h
(a) Shu, C.; Wang, Y.-H.; Zhou, B.; Li, X.-L.; Ping, Y.-F.; Lu, X.; Ye, L.-W. J. Am. Chem. Soc. 2015, 137, 9567.
(b) Shu, C.; Wang, Y.-H.; Shen, C.-H.; Ruan, P.-P.; Lu, X.; Ye, L.-W. Org. Lett. 2016, 18, 3254.
(c) Shu, C.; Shen, C.-H.; Wang, Y.-H.; Li, L.; Li, T.; Lu, X.; Ye, L.-W. Org. Lett. 2016, 18, 4630.
(d) Ruan, P.-P.; Li, H.-H.; Liu, X.; Zhang, T.; Zuo, S.-X.; Zhu, C.-Y.; Ye, L.-W. J. Org. Chem. 2017, 82, 9119.
Wu, Y.; Zhu, L.; Yu, Y.; Luo, X.; Huang, X. J. Org. Chem. 2015, 80, 11407.
doi: 10.1021/acs.joc.5b02057
Pawar, S. K.; Sahani, R. L.; Liu, R.-S. Chem. Eur. J. 2015, 21, 10843.
doi: 10.1002/chem.v21.30
Yu, Y.; Chen, G.; Zhu, L.; Liao, Y.; Wu, Y.; Huang, X. J. Org. Chem. 2016, 81, 8142.
doi: 10.1021/acs.joc.6b01948
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