Progress in Diazo Compounds Mediated Transition-Metal-Catalyzed C—H Alkylation
- Corresponding author: Hu Siqian, hbeukj@126.com Wang Feng, wangliang@jhun.edu.cn
Citation:
Wang Liang, Li Zhana, Wan Kang, Qu Xinga, Hu Siqian, Wang Feng. Progress in Diazo Compounds Mediated Transition-Metal-Catalyzed C—H Alkylation[J]. Chinese Journal of Organic Chemistry,
;2016, 36(5): 889-912.
doi:
10.6023/cjoc201511017
Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068. (b) Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030. (c) Yeung, C. S.; Dong, V. M. Chem. Rev, 2011, 111, 1215. (d) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. (e) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed.2012, 51, 10236.
Godula, K.; Sames, D. Science 2006, 312, 67. (b) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172. (c) Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593. (d) Leow, D.; Li, G.; Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518. (e) Tang, R.-Y.; Li, G.; Yu, J.-Q. Nature 2014, 507, 215.
Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (b) Daugulis, O.; Do, H. Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074. (c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. (d) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651. (e) Ackermann, L. Acc. Chem. Res. 2014, 47, 281. (f) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634. (b) Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am.Chem. Soc 2008, 130, 7190.
Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc.2006, 128, 78.
Ackermann, L. Chem. Commun. 2010, 46, 4866.
Lee, D.-H.; Kwon, K.-H.; Yi, C.-S. Science 2011, 333, 1613.
Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814. (b) Li, Y.; Li, B.-J.; Wang, W.-H.; Huang, W.-P.; Zhang, X.-S.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 2115.
Pan, S.; Shibata, T. ACS Catal. 2013, 3, 704.
Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507. (b) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577. (c) Hu, F.; Xia, Y.; Ma, C.; Zhang, Y.; Wang, J. Chem. Commun. 2015, 51, 7986. (d) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236.
Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc.2012, 134, 13565.
Yu, X.; Yu, S.; Xiao, J.; Wan, B.; Li, X. J. Org. Chem. 2013, 78, 5444.
Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888.
Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908.
Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed.2014, 53, 1364.
Cacchi, S.; Fabrizi, G. Chem.Rev.2005, 105, 2873.
Shi, J.; Yan, Y.; Li, Q.; Xu, H. E.; Yi, W. Chem.Commun. 2014, 50, 6483.
Kimyonok, A.; Wang, X. Y.; Weck, M. Polym. Rev.2006, 46, 47. (b) Yan, G.; Borah, A. J.; Yang, M. Adv. Synth. Catal. 2014, 356, 2375.
Jeong, J.; Patel, P.; Hwang, H.; Chang, S. Org. Lett.2014, 16, 4598.
Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003. (b) Wang, D.-S.; Chen, Q.-A.; Li, W.; Yu, C.-B.; Zhou, Y.-G.; Zhang, X. J. Am. Chem. Soc.2010, 132, 8909.
Song, Z.; Samanta, R.; Antonchick, A. P. Org. Lett.2013, 15, 5662.
Ai, W.; Yang, X.; Wu, Y.; Wang, X.; Li, Y.; Yang, Y.; Zhou, B. Chem. Eur. J. 2014, 20, 17653.
Xia, Y.; Liu, Z.; Feng, S.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 223.
Zhou, J.; Shi, J.; Liu, X.; Jia, J.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun.2015, 51, 5868.
Iagafarova, I. E.; Vorobyeva, D. V.; Peregudov, A. S.; Osipov, S. N. Eur. J. Org. Chem. 2015, 4950.
Liu, X.-G.; Zhang, S.-S.; Wu, J.-Q.; Li, Q.; Wang, H. Tetrahedron Lett. 2015, 56, 4093.
Li, H.; Li, P.; Zhao, Q.; Wang, L. Chem. Commun. 2013, 49, 9170. (b) Li, H.; Xi, X.; Wang, L. Chem. Commun.2014, 50, 4218. (c) Lian, Y.; Bergman, R. G.; Lavis, L. D.; Ellman, J. A. J. Am. Chem. Soc.2013, 135, 7122.
Sharma, S.; Han, S. H.; Han, S.; Ji, W.; Oh, J.; Lee, S.-Y.; Oh, J. S.; Jung, Y. H.; Kim, I. S. Org. Lett. 2015, 17, 2852.
Zhou, J.; He, J.; Wang, B.; Yang, W.; Ren, H. J. Am. Chem. Soc. 2011, 133, 6868. (b) Wang, C.; Chen, H.; Wang, Z.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2012, 51, 7242. (c) Wang, C.; Sun, H.; Fang, Y.; Huang, Y. Angew. Chem., Int. Ed. 2013, 52, 5795.
Zhang, S.-S.; Jiang, C.-Y.; Wu, J.-Q.; Liu, X.-G.; Li, Q.; Huang, Z.-S.; Li, D.; Wang, H. Chem. Commun. 2015, 51, 10240.
Choi, M.; Park, J.; Mishra, N. K.; Lee, S.-Y.; Kim, J. H.; Jeong, K. M.; Lee, J.; Jung, Y. H.; Kim, I. S. Tetrahedron Lett. 2015, 56, 4678.
Wang, L.; Li, Z.; Qu, X.; Peng, W.-M.; Hu, S.-Q.; Wang, H.-B. Tetrahedron Lett.2015, 56, 6214.
Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc.2013, 135, 5364.
Lam, H.-W.; Man, K.-Y.; Chan, W.-W.; Zhou, Z.; Yu, W.-Y. Org. Biomol. Chem. 2014, 12, 4112.
Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 12426.
Liang, Y.; Yu, K.; Li, B.; Xu, S.; Song, H.; Wang, B. Chem. Commun. 2014, 50, 6130.
Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242. (b) Chu, L.; Xiao, K.-J.; Yu, J.-Q. Science 2014, 346, 451. (c) Shibata, T.; Shizuno, T. Angew. Chem., Int. Ed. 2014, 53, 5410.
Zhang, Y.; Wang, D.; Cui, S. Org. Lett. 2015, 17, 2494.
Zhou, B.; Chen, Z.; Yang, Y.; Ai, W.; Tang, H.; Wu, Y.; Zhu, W.; Li, Y. Angew. Chem., Int. Ed. 2015, 54, 12121.
Yang, Y.; Wang, X.; Li, Y.; Zhou, B. Angew. Chem., Int. Ed. 2015, 54, 15400.
Shi, Z.; Koester, D. C. Boultadakis-Arapinis, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 12204.
Shi, J.; Zhou, J.; Yan, Y.; Jia, J.; Liu, X.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 668.
Li, X. G.; Sun, M.; Liu, K.; Jin, Q.; Liu, P. N. Chem. Commun. 2015, 51, 2380.
Zhao, D.; Kim, J. H.; Stegemann, L.; Strassert, C. A.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 4508
Son, J.-Y.; Kim, S.; Jeon, W. H.; Lee, P. Org. Lett. 2015, 17, 2518.
Wu, J.-Q.; Yang, Z.; Zhang, S.-S.; Jiang, C.-Y.; Li, Q.; Huang, Z.-S.; Wang, H. ACS Catal. 2015, 5, 6453.
Cui, S.; Zhang, Y.; Wang, D.; Wu, Q. Chem. Sci. 2013, 4, 3912.
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