Progress in Diazo Compounds Mediated Transition-Metal-Catalyzed C—H Alkylation

doi:10.6023/cjoc201511017

Abstract

Diazo compounds had been widely employed as a class of environment friendly and highly efficient coupling reagents in transition-metal-catalyzed C—H bonds insertion reactions. Recently, C—H alkylation of various arenes and heteroarenes has been achieved enormous successes using diazo compounds as the alkylation reagents under a new catalytic model. The recent progress in diazo compounds mediated transition-metal-catalyzed C—H alkylation and tandem C—H alkylation/cyclization is reviewed, including reaction mechanism and synthetic applications. Furthermore, the prospects of this reaction are also discussed.

Key words: diazo compounds, transition-metal-catalysis, C—H activation, alkyaltion

Cite this article

Wang Liang, Li Zhana, Wan Kang, Qu Xinga, Hu Siqian, Wang Feng. Progress in Diazo Compounds Mediated Transition-Metal-Catalyzed C—H Alkylation[J]. Chin. J. Org. Chem., 2016, 36(5): 889-912.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) 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.
[2] (a) Trost, B. M. Science 1991, 254, 1471.
(b) Lu, X. Prog. Chem. 1998, 10, 123 (in Chinese).
(陆熙炎, 化学进展, 1998, 10, 123.) (c) You, S.-L.; Xia, J.-B. Top. Curr. Chem.2009, 292, 165.
(d) Luo, H.; Zhang, Z.; Liu, H.; Liu, H. Chin. J. Org. Chem. 2015, 35, 802 (in Chinese).
(罗海清, 张志鹏, 刘海东, 柳辉金, 有机化学, 2015, 35, 802.) (e) Zhang, J.; Lu, Q.; Liu, C.; Lei, A. Chin. J. Org. Chem.2015, 35, 743 (in Chinese).
(张剑, 陆庆全, 刘超, 雷爱文, 有机化学, 2015, 35, 743.)
[3] (a) 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.
[4] (a) 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.
[5] (a) Xu, J.; Wei, Z.; Li, J. Chin. J. Org. Chem. 2012, 32, 1208 (in Chinese).
(徐娟, 魏真, 李加荣, 有机化学, 2012, 32, 1208.) (b) Yu, H.; Su, S.; Zhang, C.; Dang, Z.-M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese).
(于海珠, 苏圣钦, 张弛, 党智敏, 有机化学, 2013, 33, 1628.) (c) Li, D.; He, C.; Cai, H.; Wang, G. Chin. J. Org. Chem. 2013, 33, 203 (in Chinese).
(李丹丹, 何程林, 蔡海婷, 王官武, 有机化学, 2013, 33, 203.) (d) Hu, Z.; Tong, X.; Liu, G. Chin. J. Org. Chem. 2015, 35, 539 (in Chinese).
(胡志勇, 童晓峰, 刘桂霞, 有机化学, 2015, 35, 539.) (e) Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487 (in Chinese).
(张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
[6] (a) 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.
[7] Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc.2006, 128, 78.
[8] Ackermann, L. Chem. Commun. 2010, 46, 4866.
[9] Lee, D.-H.; Kwon, K.-H.; Yi, C.-S. Science 2011, 333, 1613.
[10] (a) 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.
[11] (a) Yu, S.-C.; Ma, S.-M. Chin. J. Org. Chem. 2002, 22, 307 (in Chinese).
(余世超, 麻生明, 有机化学, 2002, 22, 307.) (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev.2010, 110, 624.
[12] Pan, S.; Shibata, T. ACS Catal. 2013, 3, 704.
[13] (a) 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.
[14] (a) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
(b) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev.2010, 110, 704.
(c) Davies, H. M. L.; Hedley, S. J. Chem. Soc. Rev. 2007, 36, 1109.
(d) Chen, B.; Liang, F.-T.; Hou, Y.-H.; Wang, J.-B. Chin. J. Org. Chem. 2000, 20, 433 (in Chinese).
(陈蓓, 梁锋廷, 侯益华, 王剑波, 有机化学, 2000, 20, 433.)
[15] Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc.2012, 134, 13565.
[16] Yu, X.; Yu, S.; Xiao, J.; Wan, B.; Li, X. J. Org. Chem. 2013, 78, 5444.
[17] Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888.
[18] Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908.
[19] Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed.2014, 53, 1364.
[20] Cacchi, S.; Fabrizi, G. Chem.Rev.2005, 105, 2873.
[21] Shi, J.; Yan, Y.; Li, Q.; Xu, H. E.; Yi, W. Chem.Commun. 2014, 50, 6483.
[22] (a) 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.
[23] Liu, Y.; Zhang, Y.; Fei, H.; Jin, X. Chin. J. Org. Chem. 2013, 33, 267 (in Chinese).
(刘雅莉, 张韻慧, 费红艳, 晋兴华, 有机化学, 2013, 33, 267.)
[24] Jeong, J.; Patel, P.; Hwang, H.; Chang, S. Org. Lett.2014, 16, 4598.
[25] (a) 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.
[26] Song, Z.; Samanta, R.; Antonchick, A. P. Org. Lett.2013, 15, 5662.
[27] Ai, W.; Yang, X.; Wu, Y.; Wang, X.; Li, Y.; Yang, Y.; Zhou, B. Chem. Eur. J. 2014, 20, 17653.
[28] Xia, Y.; Liu, Z.; Feng, S.; Zhang, Y.; Wang, J. J. Org. Chem. 2015, 80, 223.
[29] Zhou, J.; Shi, J.; Liu, X.; Jia, J.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun.2015, 51, 5868.
[30] (a) Nie, J.; Guo, H.; Cahard, D.; Ma, J. Chem. Rev. 2011, 111, 455.
(b) Qing, F. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
(卿凤翎, 有机化学, 2012, 32, 815.) (c) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).
(潘菲, 施章杰, 化学学报, 2012, 70, 1679.) (d) Lü, C.; Shen, Q.; Liu, D. Chin. J. Org. Chem.2012, 32, 1380 (in Chinese).
(吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.)
[31] Iagafarova, I. E.; Vorobyeva, D. V.; Peregudov, A. S.; Osipov, S. N. Eur. J. Org. Chem. 2015, 4950.
[32] Liu, X.-G.; Zhang, S.-S.; Wu, J.-Q.; Li, Q.; Wang, H. Tetrahedron Lett. 2015, 56, 4093.
[33] (a) 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.
[34] 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.
[35] (a) 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.
[36] Wang, D.; Cui, S. Tetrahedron 2016, 72, 2725.
[37] 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.
[38] 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.
[39] Wang, L.; Li, Z.; Qu, X.; Peng, W.-M.; Hu, S.-Q.; Wang, H.-B. Tetrahedron Lett.2015, 56, 6214.
[40] Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc.2013, 135, 5364.
[41] Lam, H.-W.; Man, K.-Y.; Chan, W.-W.; Zhou, Z.; Yu, W.-Y. Org. Biomol. Chem. 2014, 12, 4112.
[42] Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 12426.
[43] Liang, Y.; Yu, K.; Li, B.; Xu, S.; Song, H.; Wang, B. Chem. Commun. 2014, 50, 6130.
[44] (a) 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.
[45] Ye, B.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 7896.
[46] (a) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608.
(b) Wang, L.; Guo, W.; Zhang, X.-X.; Xia, X.-D.; Xiao, W.-J. Org. Lett. 2012, 14, 740.
(c) Xie, W.; Zuo, Z.; Zi, W.; Ma, D. Chin. J. Org. Chem.2013, 33, 869 (in Chinese).
(谢卫青, 左智伟, 资伟伟, 马大为, 有机化学, 2013, 33, 869.) (d) Zhang, D.; Qin, Y. Acta Chim. Sinica2013, 71, 147 (in Chinese).
(张丹, 秦勇, 化学学报, 2013, 71, 147.) (e) Wang, L.; Qu, X.; Li, Z.; Peng, W. Chin. J. Org. Chem. 2015, 35, 688 (in Chinese).
(王亮, 瞿星, 李站, 彭望明, 有机化学, 2015, 35, 688.)
[47] Zhang, Y.; Zheng, J.; Cui, S. J. Org. Chem. 2014, 79, 6490.
[48] Zhang, Y.; Wang, D.; Cui, S. Org. Lett. 2015, 17, 2494.
[49] Zhou, B.; Chen, Z.; Yang, Y.; Ai, W.; Tang, H.; Wu, Y.; Zhu, W.; Li, Y. Angew. Chem., Int. Ed. 2015, 54, 12121.
[50] Yang, Y.; Wang, X.; Li, Y.; Zhou, B. Angew. Chem., Int. Ed. 2015, 54, 15400.
[51] (a) Du, D.; Fang, J.-X. Chin. J. Org. Chem. 2007, 27, 1318 (in Chinese).
(杜鼎, 方建新, 有机化学, 2007, 27, 1318.) (b) Zhou, Y.-D.; Zeng, H.-P.; Jing, H.-L.; Yuan, G.-Z.; Ouyang, X.-H. Chin. J. Org. Chem. 2006, 26, 783 (in Chinese).
(周亚东, 曾和平, 靖慧莲, 袁国赞, 欧阳新华, 有机化学, 2006, 26, 783.) (c) Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459.
(d) Henry, G. D. Tetrahedron 2004, 60, 6043.
(e) Michael, J. P. Nat. Prod. Rep.2005, 22, 627.
[52] Shi, Z.; Koester, D. C. Boultadakis-Arapinis, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 12204.
[53] Shi, J.; Zhou, J.; Yan, Y.; Jia, J.; Liu, X.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 668.
[54] Li, X. G.; Sun, M.; Liu, K.; Jin, Q.; Liu, P. N. Chem. Commun. 2015, 51, 2380.
[55] Zhao, D.; Kim, J. H.; Stegemann, L.; Strassert, C. A.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 4508
[56] Cheng, Y.; Bolm, C. Angew. Chem., Int. Ed.2015, 54, 12349.
[57] Son, J.-Y.; Kim, S.; Jeon, W. H.; Lee, P. Org. Lett. 2015, 17, 2518.
[58] Wu, J.-Q.; Yang, Z.; Zhang, S.-S.; Jiang, C.-Y.; Li, Q.; Huang, Z.-S.; Wang, H. ACS Catal. 2015, 5, 6453.
[59] Cui, S.; Zhang, Y.; Wang, D.; Wu, Q. Chem. Sci. 2013, 4, 3912.

重氮参与的过渡金属催化C—H烷基化反应研究进展