Recent Advances in the α-C(sp3)-H Bond Functionalization of Glycine Derivatives

doi:10.6023/cjoc201903006

Abstract

α-Amino acids are the units of proteins, which not only widely occur in many biological important compounds and natural products, but also are useful as organic catalysts or ligands for asymmetric synthesis. Among them, glycines are particularly useful building blocks in organic synthesis. Direct C(sp³)-H bond functionalization of glycine derivatives provided an attractive synthesis strategy for the construction of a variety of α-substituted α-amino acids. The recent progress in the α-C(sp³)-H bond activation of glycine derivatives, with various reagents to form carbon-carbon and carbon-heteroatom bond, and oxidative coupling/cyclization reaction involving glycine derivatives is reviewed.

Key words: glycines, C-H bond, functionalization, cross-dehydrogenative-coupling, cascade cyclization

Cite this article

Zhu Zhiqiang, Xiao Lijin, Xie Zongbo, Le Zhanggao. Recent Advances in the α-C(sp³)-H Bond Functionalization of Glycine Derivatives[J]. Chin. J. Org. Chem., 2019, 39(9): 2345-2364.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Pollegioni, L.; Servi, S. Non-natural Amino Acids:Methods and Protocols, Springer, New York, 2012.
(b) Hughes, A. B. Amino Acids, Peptides and Proteins in Organic Chemistry, Wiley VCH, Weinheim, 2011.
[2] (a) Soloshonok, V. A.; Izawa, K. Asymmetric Synthesis and Application of α-Amino Acids, American Chemical Society, Washington DC, 2009, Vol. 1009.
(b) He, G.; Wang, B.; Nack, W. A.; Chen, G. Acc. Chem. Res. 2016, 49, 635.
(c) Bhat, S. V.; Nagasampagi, B. A.; Sivakumar, M. Chemistry of Natural Products, Springer, Berlin, 2005, p. 317.
(d) Li, X.; Xiong, W.; Ding, Q. Chin. J. Org. Chem. 2019, 39, 1874(in Chinese). (李小芳, 熊伟康, 丁秋平, 有机化学, 2019, 39, 1874.)
[3] (a) Albericio, F.; Kruger, H. G. Future Med. Chem. 2012, 4, 1527.
(b) Craik, D. J.; Fairlie, D. P.; Liras, S.; Price, D. Chem. Biol. Drug Des. 2013, 81, 136.
(c) Kaspar, A. A.; Reichert, J. M. Drug Discovery Today 2013, 18, 807.
[4] (a) Noisier, A. F. M.; Brimble, M. A. Chem. Rev. 2014, 114, 8775.
(b) Metz, A. M.; Kozlowski, M. C. J. Org. Chem. 2015, 80, 1.
[5] (a) Bauer, M.; Wang, W.; Lorion, M. M.; Dong, C.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 203.
(b) Stepan, A. F.; White, M. C. Nature 2016, 537, 214.
(c) Uhlig, T.; Kyprianou, T.; Martinelli, F. G.; Oppici, C. A.; Heiligers, D.; Heiligers, D.; Hills, X. R.; Calvo, P. V. Eup. Open Proteomics 2014, 4, 58.
(d) Xiao, H.; Chatterjee, A.; Choi, S. H.; Bajjuri, K. M.; Sinha, S. C.; Schultz, P. G. Angew. Chem., Int. Ed. 2013, 52, 14080.
[6] (a) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
(b) Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8.
(c) Petasis, N. A.; Zavialov, A. I. J. Am. Chem. Soc. 1997, 119, 445.
[7] (a) Bayer, A.; Kazmaier, U. J. Org. Chem. 2014, 79, 8491.
(b) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
[8] (a) Brown, Jihn. M.; Cooley, Nei. A. Chem. Rev. 1988, 88, 1031.
(b) Godula, K.; Sames, D. Science 2006, 312, 67.
(c) Bergman, R. G. Nature 2007, 446, 391.
[9] (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(b) Sun, C.; L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
(c) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857.
(d) Zhang, J.; Lu, Q. Q.; Liu, C.; Lei, A. W. 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.)
(e) Pei, P. K.; Zhang, F.; Yi, H.; Lei, A. W. Acta Chim. Sinica 2017, 75, 15(in Chinese). (裴朋昆, 张凡, 易红, 雷爱文, 化学学报, 2017, 75, 15.)
[10] (a) Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J. Q. Acc. Chem. Res. 2012, 45, 788.
(b) Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911.
(c) Yang, L.; Huang, H. Chem. Rev. 2015, 115, 3468.
(d) Dong, Z.; Ren, Z.; Thompson, S. J.; Xu, Y.; Dong, G. Chem. Rev. 2017, 117, 9333.
(e) Liu, W.; Zheng, X, Y.; Zeng, J. G.; Cheng, P. Chin. J. Org. Chem. 2017, 37, 1(in Chinese). (刘薇, 郑昕宇, 曾建国, 程辟, 有机化学, 2017, 37, 1.)
[11] (a) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.
(b) Li, C. J. Acc. Chem. Res. 2009, 42, 335.
[12] (a) Zhu, Z. Q.; Bai, P.; Huang, Z. Z. Org. Lett. 2014, 16, 4881.
(b) Salman, M.; Zhu, Z. Q.; Huang, Z. Z. Org. Lett. 2016, 18, 1526.
(c) Zhu, Z. Q.; Xie, Z. B.; Le, Z. G. J. Org. Chem. 2016, 81, 9449.
(d) Zhu, Z. Q.; Xie, Z. B.; Le, Z. G. Synlett. 2017, 28, 485.
(e) Zhu, Z. Q.; Xiao L. J.; Chen, Y.; Zhu, H. B.; Xie, Z. B.; Le, Z. G. Synthesis 2018, 50, 2775.
(f) Xiao L. J.; Zhu, Z. Q.; Guo, D.; Xie, Z. B.; Lu, Y.; Le, Z. G. Synlett 2018, 29, 1659.
(g) Zhu, Z. Q.; Xiao L. J.; Zhou, C. C.; Song, H. L.; Xie, Z. B.; Le, Z. G. Tetrahedron Lett. 2018, 59, 3326.
(h) Zhu, Z. Q.; Xiao L. J.; Guo, D.; Chen, X.; Ji, J. J.; Zhu, X.; Xie, Z. B.; Le, Z. G. J. Org. Chem. 2019, 84, 435.
[13] (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640.
(b) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170.
(c) Prier, C. K.; Rankic, D. A.; Mac Millan, D. W. C. Chem. Rev. 2013, 113, 5322.
[14] Luo, Y. R. Handbook of Bond Dissociation Energy in Organic Compound, CRC Press, Boca Raton, 2002.
[15] (a) Li, Z.; Bohle, D. S.; Li, C. J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 8928.
(b) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2006, 128, 56.
[16] Zhao, L.; Li, C. J. Angew. Chem., Int. Ed. 2008, 47, 7075.
[17] Luo, M. H.; Jiang, Y. Y.; Xu, K.; Liu, Y. G.; Sun, B. G.; Zeng, C. C. Beilstein J. Org. Chem. 2018, 14, 499.
[18] Sud, A.; Sureshkumar, D.; Klussmann, M. Chem. Commun. 2009, 3169.
[19] Xie, J.; Huang, Z. Z. Angew. Chem., Int. Ed. 2010, 49, 10181.
[20] Liu, P.; Wang, Z.; Lin, J.; Hu, X. Eur. J. Org. Chem. 2012, 2012, 1583.
[21] Gao, X. W.; Meng, Q. Y.; Xiang, M.; Chen, B.; Feng, K.; Tung, C. H.; Wu, L. Z. Adv. Synth. Catal. 2013, 355, 2158.
[22] Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429.
[23] Tan, Y. Q.; Yuan, W.; Gong, L.; Meggers, E. Angew. Chem., Int. Ed. 2015, 127, 13237.
[24] (a) Deng, G. J.; Zhao, L.; Li, C. J. Angew. Chem., Int. Ed. 2008, 47, 6278.
(b) Ochiai, M.; Miyamato, K.; Kaneaki, T.; Hayashi, S.; Nakanishi, W. Science 2011, 332, 448.
(c) Tran, B.; Li, B.; Driess, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 2555.
[25] Forkin, A. A.; Schreiner, P. R. Chem. Rev. 2002, 102, 1551.
[26] Wei, W. T.; Song, R. J.; Li, J. H. Adv. Synth. Catal. 2014, 356, 1703.
[27] Peng, H.; Yu, J. T.; Jiang, Y.; Yang, H.; Cheng, J. J. Org. Chem. 2014, 79, 9847.
[28] San Segundo, M.; Guerrero, I.; Correa, A. Org. Lett. 2017, 19, 5288.
[29] Mutra, M. R.; Dhandabani, G. K.; Wang, J. J. Adv. Synth. Catal. 2018, 360, 3960.
[30] Segundo, M. S.; Correa, A. ChemSusChem. 2018, 11, 3893.
[31] Li, K.; Tan, G.; Huang, J.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 12942.
[32] Li, K.; Wu, Q.; Lan, J.; You, J. S. Nat. Chem. 2015, 6, 8404.
[33] Tan, M.; Li, K.; Yin, J.; You, J. Chem. Commun. 2018, 54, 1221.
[34] (a) Inagaki, A.; Akita, M. Coord. Chem. Rev. 2010, 254, 1220.
(b) Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102.
(c) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687.
(d) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[35] (a) McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114.
(b) Petronijevic, F. R.; Nappi, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 18323.
(c) Pirnot, M. T.; Rankic, D. A.; Martin, D. B.; MacMillan, D. W. C. Science 2013, 339, 1593.
[36] Xuan, J.; Zeng, T. T.; Feng, Z. J.; Deng, Q. H.; Chen, J. R.; Lu, L. Q.; Xiao, W. J.; Alper H. Angew. Chem., Int. Ed. 2015, 54, 1625.
[37] Ding, W.; Lu, L. Q.; Liu, J.; Liu, D.; Song, H. T.; Xiao W. J. J. Org. Chem. 2016, 81, 7237.
[38] Wang, C.; Guo, M. Z.; Qi, R. P.; Shang, Q. Y.; Liu, Q. Y.; Wang, S.; Zhao, L.; Wang, R.; Xu, Z. Q. Angew. Chem., Int. Ed. 2018, 130, 16067.
[39] (a) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.
(b) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968.
(c) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810.
[40] Xie, Z.; Liu, X.; Liu, L. Org. Lett. 2016, 18, 2982.
[41] (a) Muller, J.; Saunders, J. O. F.; Salituro, G.; Travins, J. M.; Yan, S.; Zhao, F.; Su, S. M. ACS Med. Chem. Lett. 2012, 3, 850.
(b) Zhang, L.; Wang, X.; Li, X.; Xu, W. J. Enzyme. Inhib. Med. Chem. 2014, 29, 333.
(c) Weigel, L. F.; Nitsche, C.; Graf, D.; Bartenschlager, R.; Klein, C. D. J. Med. Chem. 2015, 58, 7719.
[42] (a) Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1991, 56, 6939.
(b) Buyck, T.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2013, 52, 12714.
[43] (a) Shirakawa, S.; Maruoka, K. Angew. Chem., Int. Ed. 2013, 52, 4312.
(b) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.
[44] Zhao, L.; Baslé, O.; Li, C. J. Proc. Natl. Acd. Sci. U. S. A. 2009, 106, 4106.
[45] Zhu, S. Q.; Rueping, M. Chem. Commun. 2012, 48, 11960.
[46] Wang, Z. Q.; Hu, M.; Huang, X. C.; Gong, L. B.; Xie, Y. X.; Li, J. H. J. Org. Chem. 2012, 77, 8705.
[47] Huo, C.; Wang, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y. Adv. Synth. Catal. 2014, 356, 411.
[48] Huo, C.; Yuan, Y.; Wu, M.; Jia, X.; Wang, X.; Chen, F.; Tang, J. Angew. Chem. 2014, 53, 13544.
[49] Gao, X. W.; Meng, Q. Y.; Li, J. X.; Zhong, J. J.; Lei, T.; Li, X. B.; Tung, C. H.; Wu, L. Z. ACS Catal. 2015, 5, 2391.
[50] Zhang, Y.; Ni, M. J.; Feng, B. N. Org. Biomol. Chem. 2016, 14, 1550.
[51] Wu, J. C.; Song, R. J.; Wang, Z. Q.; Huang, X. C.; Xie, Y. X.; Li, J. H. Angew. Chem., Int. Ed. 2012, 51, 3453.
[52] Huo, C.; Wang, C.; Sun, C.; Jia, X.; Wang, X.; Chang, W.; Wu, M. Adv. Synth. Catal. 2013, 355, 1911.
[53] Li, S. L.; Yang, X. R.; Wang, Y. W.; Zhou, H.; Zhang, B. Y.; Huang, G. X.; Zhang, Y.; Li Y. Adv. Synth. Catal. 2018, 360, 4452.
[54] Zhou, J. L.; Liu, J. C.; Chen, Q. Y. Chin. J. Org. Chem. 2009, 29, 1708(in Chinese). (周建良, 刘建超, 陈启元, 有机化学, 2009, 29, 1708.)
[55] Jin, C. A.; Xu, Q.; Feng, G. F.; Jin, Y.; Zhang, L. Y. Chin. J. Org. Chem. 2018, 38, 775(in Chinese). (金城安, 徐庆, 冯高峰, 金阳, 张连阳, 有机化学, 2018, 38, 775.)
[56] Jiao, J.; Zhang, J. R.; Liao, Y. Y.; Xu, L.; Hu, M.; Tang, R. Y. RSC Adv. 2017, 7, 30152.
[57] Ramana, D. V.; Chowhan, L. R.; Chandrasekharam, M. ChemistrySelect 2017, 2, 2241.
[58] Wei, Y. Y.; Wang, J.; Wang, Y. J.; Yao, X. Q.; Yang, C. X.; Huo, C. Org. Biomol. Chem. 2018, 16, 4985.
[59] Gao, Y. Z.; Tang, G.; Zhao, Y. F. Chin. J. Org. Chem. 2018, 38, 62(in Chinese). (高玉珍, 唐果, 赵玉芬, 有机化学, 2018, 38, 62.)
[60] Baslé, O.; Li, C. J. Chem. Commun. 2009, 4124.
[61] Yang, B.; Yang, T. T.; Li, X. A.; Wang, J. J.; Yang, S. D. Org. Lett. 2013, 15, 5024.
[62] Zhi, H.; Ung, S. P. M.; Liu, Y.; Zhao, L.; Li, C. J. Adv. Synth. Catal. 2016, 358, 2553.
[63] Jia, X.; Liu, X.; Shao, Y.; Yuan, Y.; Zhu, Y.; Hou, W.; Zhang, X. Adv. Synth. Catal. 2017, 359, 4399.
[64] Liu, X. X.; Wu, Z. Y.; He, Y. Q.; Zhou, X. Q.; Hu, T.; Ma, C. W.; Huang, G. S. Adv. Synth. Catal. 2016, 358, 2385.
[65] Chen, C.; Zhu, M. H.; Jiang, L. H.; Zeng, Z. B.; Yi, N. N.; Xiang, J. N. Org. Biomol. Chem. 2017, 15, 8134.
[66] Daggupati, R.; Malapak, C. Org. Chem. Front. 2018, 5, 788.
[67] Liu, X.; Pu, J.; Luo, X.; Cui, X.; Wu, Z.; Huang, G. Org. Chem. Front. 2018, 5, 361.
[68] (a) Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 953.
(b) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 2039.
[69] Richter, H.; García Mancheño, O. Org. Lett. 2011, 13, 6066.
[70] Liu, P.; Wang, Z.; Lin, J.; Hu, X. Eur. J. Org. Chem. 2012, 1583.
[71] Rohlmann, R.; Stopka, T.; Richter, H.; Mancheño, O. J. Org. Chem. 2013, 78, 6050.
[72] Jia, X.; Peng, F.; Qing, C.; Huo, C.; Wang, X. Org. Lett. 2012, 14, 4030.
[73] Jia, X.; Huo, W.; Shao, Y.; Yuan, Y.; Chen, Q.; Li, P.; Liu, X.; Ji, H. Chem.-Eur. J. 2017, 23, 12980.
[74] Jia, X. D.; Wang, Y.; Peng, F.; Huo, C.; Yu, L.; Liu, J.; Wang, X. Adv. Synth. Catal. 2014, 356, 1210.
[75] (a) Bolm, C.; Legros, J.; Le Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217.
(b) Bauer, I.; Knölker, H. J. Chem. Rev. 2015, 115, 3170.
[76] Li, Z.; Cao, L.; Li, C. J. Angew. Chem., Int. Ed. 2007, 46, 6505.
[77] Huo, C.; Chen, F.; Yuan, Y.; Xie, H.; Wang, Y. Org. Lett. 2015, 17, 5028.
[78] Huo, C.; Yuan, Y.; Chen, F.; Wang, Y. Adv. Synth. Catal. 2015, 357, 3648.
[79] Huo, C.; Xie, H.; Chen, F.; Tang, J.; Wang, Y. Adv. Synth. Catal. 2016, 358, 724.
[80] Wei, W. T.; Li, H. B.; Song, R. J.; Li, J. H. Chem. Commun. 2015, 51, 11325.
[81] (a) Jia, X.; Wang, Y.; Peng, F.; Huo, C.; Yu, L.; Liu, J.; Wang, X. J. Org. Chem. 2013, 78, 9450.
(b) Wang, Y.; Peng, F.; Liu, J.; Huo, C.; Wang, X.; Jia, X. J. Org. Chem. 2015, 80, 609.
(c) Liu, J.; Wang, Y.; Yu, L.; Huo, C.; Wang, X.; Jia, X. Adv. Synth. Catal. 2014, 356, 3214.
(d) Liu, G.; Quian, J.; Hua, J.; Cai, F.; Li, X.; Liu, L. Org. Biomol. Chem. 2016, 14, 1147.
(e) Xie, Z.; Jia, J.; Liu, X.; Liu, L. Adv. Synth. Catal. 2016, 358, 919.
(e) Ni, M.; Zhang, Y.; Gong, T.; Feng, B. Adv. Synth. Catal. 2017, 359, 824.
(f) Yang, X.; Li, L.; Li, Y.; Zhang, Y. J. Org. Chem. 2016, 81, 12433.
(g) Liu, X.; Shao, Y.; Li, P.; Ji, H.; Yuan, Y.; Jia, X. Tetrahedron Lett. 2018, 59, 637.
(h) Meng, Q. Y.; Gao, X. W.; Lei, T.; Liu, Z.; Zhan, F.; Li, Z. J.; Zhong, J. J.; Xiao, H.; Feng, K.; Chen, B.; Tao, Y.; Tung, C. H.; Wu, L. Z. Sci. Adv. 2017, 3, e1700666.
[82] Deng, Q. H.; Zou, Y. Q.; Lu, L. Q.; Tang, Z. L.; Chen, J. R.; Xiao, W. J. Chem.-Asian J. 2014, 9, 2432.
[83] Li, Y. J.; Li, X.; Zhang, S. X.; Zhao, Y. L.; Liu, Q. Chem. Commun. 2015, 51, 11565.
[84] Huo, C.; Yuan, Y.; Chen, F.; Tang, J.; Wang, Y. Org. Lett. 2015, 17, 4208.
[85] Xie, J.; Huang, Y.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2017, 19, 6056.
[86] Li, H.; Huang, S.; Wang, Y.; Huo, C. Org. Lett. 2018, 20, 92.
[87] Tang, L.; Li, X. M.; Matuska, J. H.; He, Y. H.; Guan, Z. Org. Lett. 2018, 20, 5618.

甘氨酸衍生物α-C(sp³)-H键官能团化反应的研究进展

Recent Advances in the α-C(sp³)-H Bond Functionalization of Glycine Derivatives

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447.
[2]	Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.
[3]	Yanshuo Zhu, Hongyan Wang, Penghua Shu, Ke'na Zhang, Qilin Wang. Recent Advances on Alkoxy Radicals-Mediated C(sp³)—H Bond Functionalization via 1,5-Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 1-17.
[4]	Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136.
[5]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[6]	Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.
[7]	Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527.
[8]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[9]	Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.
[10]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[11]	Linsheng Bai, Peng Hong, Anguo Ying. Research Progress of Functional Polyacrylonitrile Fiber in Promoting Organic Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1241-1270.
[12]	Yannian Pan, Xiao Qin, Chengkai Yuan, Yi Lu. Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 924-948.
[13]	Hongyu Hou, Yuanyuan Cheng, Bin Chen, Chenho Tung, Lizhu Wu. α-Acylation of Olefins via Photocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1012-1022.
[14]	Luomo Li, Xiaohui Yang. Recent Advances in Ionic Transfer Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1036-1044.
[15]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.

甘氨酸衍生物α-C(sp3)-H键官能团化反应的研究进展