自由基促进的醇/醚α-O-C(sp3)-H键选择性活化的最新研究进展
收稿日期: 2015-06-12
网络出版日期: 2015-10-12
基金资助
项目受国家自然科学基金(Nos.21272096,21472080)资助.
Recent Advances in Free-Radical-Promoted Selective Activation of Alcohol/Ether α-O-C(sp3)-H Bond
Received date: 2015-06-12
Online published: 2015-10-12
Supported by
Project supported by the National Natural Science Foundation of China(Nos. 21272096 and 21472080).
尚筱洁 , 柳忠全 . 自由基促进的醇/醚α-O-C(sp3)-H键选择性活化的最新研究进展[J]. 化学学报, 2015 , 73(12) : 1275 -1282 . DOI: 10.6023/A15060407
Alcohols/ethers are the most common chemicals. And the hydroxyl group in alcohols is believed to be universal functional group in synthetic organic chemistry. It is undeniably attractive to form a new chemical bond through selective cleavage of the α-O-C(sp3)-H bond. Considerable developments in the free-radical-promoted alcohol/ether C(sp3)-H functionalization have been achieved in recent years. These methods have drawn much attention from synthetic chemists due to the features of alcohol/ether as starting materials, reservation of the hydroxyl group and excellent regioselectivity, etc. This paper summarizes the recent advances in free-radical-initiated selective activation of the α-O-C(sp3)-H bonds in alcohol/ether. For a start, the possible factors such as bond dissociation energy(BDE) and stability of the key radical intermediate that dominates the regioselectivity in radical-initiated C(sp3)-H bond activation have been analyzed here. Moreover, recent developments in this field have been demonstrated in details from different reaction types as following.(a) Minisci reactions of heterocycles with alcohols/ethers;(b) Radical addition/elimination reactions of activated alkenes with alcohols/ethers;(c) Free-radical addition/cyclization cascade reactions of activated olefins and/or biaryl isonitriles with alcohols/ethers;(d) Free-radical addition/difunctionalization and rearrangement reactions of alcohols/ethers with activated alkenes. Besides, other free radical reactions such as oxidative coupling reactions of aryl boronic acids with ethers, C-O and C-N bond formation reactions have also been exhibited. In addition, the suggested mechanisms for most of these reactions have been depicted and discussed in this review. Finally, the disadvantages of present systems and the possible modifications along with the future studies of this active area have been summarized at the end of this article.
Key words： free radical; alcohol; C-H activation; C-C bond formation; oxidative coupling
[1] Bergman, R. G. Nature 2007, 446, 391.
[2] (a) Godula, K.; Sames, D. Science 2006, 312, 67.
(b) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(c) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
(d) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857.
(e) Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362.
(f) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788.
(g) Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911.
(h) White, M. C. Science 2012, 335, 807.
(i) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
(j) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
(k) Yang, L.; Huang, H. Chem. Rev. 2015, 115, 3468.
[3] de Montellano, P. R. O. Chem. Rev. 2010, 110, 932.
[4] Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640.
[5] Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2011, 40, 1937.
[6] (a) Jia, F.; Li, Z. Org. Chem. Front. 2014, 1, 194;
(b) Ma, Y.; Li, W.; Yu, B. Acta Chim. Sinica 2013, 71, 541.(马玉勇, 李微, 俞飚, 化学学报, 2013, 71, 541.);
(c) Zhang, W.; Zhang, J.; Liu, Y.-K. Chin. J. Org. Chem. 2014, 34, 36.(张巍, 张家慧, 刘运奎, 有机化学, 2014, 34, 36.);
(d) Zhang, B.; Guan, H.; Liu, B.; Shi, B.-F. Chin. J. Org. Chem. 2014, 34, 1487.(张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.);
(e) Luo, H.-Q.; Zhang, Z.; Liu, H.; Liu, H. Chin. J. Org. Chem. 2015, 35, 802.(罗海清, 张志鹏, 刘海东, 柳辉金, 有机化学, 2015, 35, 802.)
[7] Luo, Y.-R. Handbook of Bond Dissociation Energy in Organic Compound, CRC Press, Boca Raton, 2002.
[8] Correia, C. A.; Yang, L.; Li, C.-J. Org. Lett. 2011, 13, 4581.
[9] Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489.
[10] He, T.; Yu, L.; Zhang, L.; Wang, L.; Wang, M. Org. Lett. 2011, 13, 5016.
[11] Studer, A. Chem. Soc. Rev. 2004, 33, 267.
[12] Liu, Y.; Jiang, B.; Zhang, W.; Xu, Z. J. Org. Chem. 2013, 78, 966.
[13] Bohman, B.; Berntsson, B.; Dixon, R. C. M.; Stewart, C. D.; Barrow, R. A. Org. Lett. 2014, 16, 2787.
[14] Neubert, T. D.; Schmidt, Y.; Conroy, E.; Stamos, D. Org. Lett. 2015, 17, 2362.
[15] Jin, J.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 1565.
[16] Jin, J.; MacMillan, D. W. C. Nature 2015, 525, 87.
[17] Liu, Z.-Q.; Sun, L.; Wang, J.-G.; Han, J.; Zhao, Y.-K.; Zhou, B. Org. Lett. 2009, 11, 1437.
[18] Cui, Z.; Shang, X.; Shao, X.-F.; Liu, Z.-Q. Chem. Sci. 2012, 3, 2853.
[19] Studer, A.; Curran, D. P. Nat. Chem. 2014, 6, 765.
[20] Amaoka, Y.; Nagatomo, M.; Watanabe, M.; Tao, K.; Kamijo, S.; Inoue, M. Chem. Sci. 2014, 5, 4339.
[21] Niu, B.; Zhao, W.; Ding, Y.; Bian, Z.; Pittman Jr., C. U.; Zhou, A.; Ge, H. J. Org. Chem. 2015, 80, 7251.
[22] Meng, Y.; Guo, L.-N.; Wang, H.; Duan, X.-H. Chem. Commun. 2013, 49, 7540.
[23] Zhou, Z.-Z.; Hua, H.-L.; Luo, J.-Y.; Chen, Z.-S.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Tetrahedron 2013, 69, 10030.
[24] Wei, W.-T.; Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638.
[25] Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505.
[26] Li, Z.; Fan, F.; Yang, J.; Liu, Z.-Q. Org. Lett. 2014, 16, 3396.
[27] Cao, J.-J.; Zhu, T.-H.; Wang, S.-Y.; Gu, Z.-Y.; Wang, X.; Ji, S.-J. Chem. Commun. 2014, 50, 6439.
[28] Zhou, W.; Ni, S.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2015, 17, 2724.
[29] Zhang, M.; Xie, P.; Zhao, W.; Niu, B.; Wu, W.; Bian, Z.; Pittman, Jr., C. U.; Zhou, A. J. Org. Chem. 2015, 80, 4176.
[30] Hu, M.; Fan, J.-H.; Liu, Y.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 9577.
[31] Tang, S.; Liu, K.; Liu, C.; Lei, A. Chem. Soc. Rev. 2015, 44, 1070.
[32] Chen, Z.-M.; Zhang, X.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2015, 44, 5220.
[33] Zhang, S.-Y.; Tu, Y.-Q.; Fan, C.-A.; Zhang, F.-M.; Shi, L. An-gew. Chem. Int. Ed. 2009, 48, 8761.
[34] (a) Chu, X.-Q.; Meng, H.; Zi, Y.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2014, 50, 9718;
(b) Chu, X.-Q.; Meng, H.; Zi, Y.; Xu, X.-P.; Ji, S.-J. Chem. Eur. J. 2014, 20, 17198.
[35] Du, P.; Li, H.; Wang, Y.; Cheng, J.; Wan, X. Org. Lett. 2014, 16, 6350.
[36] Cheng, J.-K.; Loh, T.-P. J. Am. Chem. Soc. 2015, 37, 42.
[37] Liu, D.; Liu, C.; Li, H.; Lei, A. Angew. Chem. Int. Ed. 2013, 52, 4453.
[38] (a) Guo, S.; Yu, J.-T.; Dai, Q.; Yang, H.; Cheng, J. Chem. Com-mun. 2014, 50, 6240;
(b) García-Cabeza, A. L.; Marín-Barrios, R.; Moreno-Dorado, F. J.; Ortega, M. J.; Vidal, H.; Gatica, J. M.; Massanet, G. M.; Guerra, F. M. J. Org. Chem. 2015, 80, 6814.
[39] Aruri, H.; Singh, U.; Sharma, S.; Gudup, S.; Bhogal, M.; Kumar, S.; Singh, D.; Gupta, V. K.; Kant, R.; Vishwakarma, R. A.; Singh, P. P. J. Org. Chem. 2015, 80, 1929.
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