Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage

doi:10.6023/cjoc201803013

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 1949-1962.DOI: 10.6023/cjoc201803013 Previous Articles Next Articles

Reviews

过渡金属催化的基于季铵盐C-N键断裂的偶联反应研究进展

李刚^a,b, 陈烨^a, 夏纪宝^b

a 贵州大学化学与化工学院贵阳 550025;
b 中国科学院兰州化学物理研究所苏州研究院羰基合成与选择氧化国家重点实验室兰州 730000

收稿日期:2018-03-12 修回日期:2018-04-08 发布日期:2018-04-27
通讯作者: 陈烨, 夏纪宝 E-mail:jibaoxia@licp.cas.cn;ychen19@gzu.edu.cn
基金资助:
国家自然科学基金（Nos.21702212，21772208，21402089）和江苏省自然科学基金（No.BK20161260）资助项目.

Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage

Li Gang^a,b, Chen Ye^a, Xia Jibao^b

a School Chemistry of Chemical Engineering, Guizhou University, Guiyang 550025;
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics(LICP), Chinese Academy of Sciences, Lanzhou 730000

Received:2018-03-12 Revised:2018-04-08 Published:2018-04-27
Contact: 10.6023/cjoc201803013 E-mail:jibaoxia@licp.cas.cn;ychen19@gzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21702212, 21772208, 21602230) and the Natural Science Foundation of Jiangsu Province (No. BK20161260).

Amines containing carbon-nitrogen (C-N) bonds are widely distributed in natural products, drug molecules and functional materials. C-N bonds are one of the most abundant and inert bonds in organic molecules. Selective cleavage of C-N bonds to construct carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds represents a new synthetic method in organic synthesis. It is difficult for the direct cleavage of C-N bond. Ammonium salts are a series of stable compounds easily obtained from amines. The recent progress of transition-metal-catalyzed cross-coupling reactions via C-N bond cleavage using ammonium salts as starting materials is summerized.

Key words: transition-metal-catalysis, ammonium salt, cross-coupling reaction, C-N bond cleavage

Cite this article

Li Gang, Chen Ye, Xia Jibao. Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage[J]. Chin. J. Org. Chem., 2018, 38(8): 1949-1962.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
(b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
(c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
(d) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
[2] (a) Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
(b) Yao, X.-Q.; Hou, X.-J.; Jiao, H.; Xiang, H.-W.; Li, Y.-W. J. Phys. Chem. A 2003, 107, 9991.
[3] (a) Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132.
(b) Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098.
(c) Koreeda, T.; Kochi, T.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 7238.
(d) Tobisu, M.; Nakamura, K.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 5587.
(e) Zhao, Y.; Snieckus, V. Org. Lett. 2014, 16, 3200.
(f) Cong, X.; Fan, F.; Ma, P.; Luo, M.; Chen, H.; Zeng, X. J. Am. Chem. Soc. 2017, 139, 15182.
[4] (a) Geng, W.; Zhang, W.-X.; Hao, W.; Xi, Z. J. Am. Chem. Soc. 2012, 134, 20230.
(b) Xie, Y.; Hu, J.; Wang, Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
(c) Hao, W.; Geng, W.; Zhang, W. X.; Xi, Z. Chem.-Eur. J. 2014, 20, 2605.
[5] Balz, G.; Schiemann, G. Ber.-Umweltbundesamt (Ger.) 1927, 60B, 1186.
[6] Brasen, W. R.; Hauser, C. R. Org. Synth. 1954, 34, 58.
[7] (a) Ouyang, K.; Hao, W.; Zhang, W.-X.; Xi, Z. Chem. Rev. 2015, 115, 12045.
(b) Wang, Q.; Su, Y.; Li, L.; Huang, H. Chem. Soc. Rev. 2016, 45, 1257.
(c) Dander, J. E.; Garg, N. K. ACS Catal. 2017, 7, 1413.
(d) Takise, R.; Muto, K.; Yamaguchi, J. Chem. Soc. Rev. 2017, 46, 5864.
(e) Gao, Y.; Ji, C.-L.; Hong, X. Sci. China:Chem. 2017, 60, 1413.
(f) Liu, J.; Yuan, S.; Song, X.; Qiu, G. Chin. J. Org. Chem. 2016, 1790.
(g) Tang, H.; Huo, X.; Meng, Q.; Zhang, W. Acta Chim. Sinica 2016, 74, 219(in Chinese). (汤淏溟, 霍小红, 孟庆华, 张万斌, 化学学报, 2016, 74, 219.)
(h) Zeng, M.; Song, C.; Cui, D. Chin. J. Org. Chem. 2017, 37, 1352(in Chinese) (曾明, 宋婵, 崔冬梅, 有机化学, 2017, 37, 1352.)
[8] (a) Eds.:de Meijere, A.; Diederich, F.; Metal-Catalyzed CrossCoupling Reactions, Wiley-VCH, Weinheim, 2004, p. 437.
(b) Eds.:de Meijere, A.; Braese, S.; Oestreich, M. Metal-Catalyzed Cross-Coupling Reactions And More, Wiley-VCH, Weinheim, 2014.
[9] Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144a.
[10] Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
[11] Terao, J.; Kambe, N. Acc. Chem. Res. 2008, 41, 1545.
[12] Wenkert, E.; Han, A.-L.; Jenny, C.-J. J. Chem. Soc., Chem. Commun. 1988, 975.
[13] (a) Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
(b) Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486.
(c) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346.
(d) Su, B.; Cao, Z.-C.; Shi, Z.-J. Acc. Chem. Res. 2015, 48, 886.
(e) Tobisu, M.; Chatani, N. Acc. Chem. Res. 2015, 48, 1717.
[14] (a) Clot, E.; Eisenstein, O.; Jasim, N.; MacGregor, S. A.; McGrady, J. E.; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333.
(b) Keyes, L.; Love, J. A. RSC Catal. Ser. 2013, 11, 159.
(c) Yang, S.-D. In Homogeneous Transition-Metal-Catalyzed C-F Sctivation, John Wiley & Sons, New York, 2015, pp. 203~268.
[15] Reeves, J. T.; Fandrick, D. R.; Tan, Z.; Song, J. J.; Lee, H.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2010, 12, 4388.
[16] Guo, W.-J.; Wang, Z.-X. Tetrahedron 2013, 69, 9580.
[17] Guisan-Ceinos, M.; Martin-Heras, V.; Tortosa, M. J. Am. Chem. Soc. 2017, 139, 8448.
[18] Ma, S.; Liu, Q.; Tang, X.; Cai, Y. Asian J. Org. Chem. 2017, 6, 1209.
[19] (a) Dieck, H. A.; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133.
(b) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
[20] Pan, Y.; Zhang, Z.; Hu, H. Synthesis 1995, 245.
[21] (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(b) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
[22] Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
[23] Buszek, K. R.; Brown, N. Org. Lett. 2007, 9, 707.
[24] de la Herrán, G.; Segura, A.; Csákÿ, A. G. Org. Lett. 2007, 9, 961.
[25] Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
[26] Maity, P.; Shacklady-McAtee, D. M.; Yap, G. P. A.; Sirianni, E. R.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280.
[27] Shacklady-McAtee, D. M.; Roberts, K. M.; Basch, C. H.; Song, Y. G.; Watson, M. P. Tetrahedron 2014, 70, 4257.
[28] Liu, X.-Y.; Zhu, H.-B.; Shen, Y.-J.; Jiang, J.; Tu, T. Chin. Chem. Lett. 2017, 28, 350.
[29] Wang, T.; Yang, S.; Xu, S.; Han, C.; Guo, G.; Zhao, J. RSC Adv. 2017, 7, 15805.
[30] Turtscher, P. L.; Davis, H. J.; Phipps, R. J. Synthesis 2018, 50, 793.
[31] Basch, C. H.; Liao, J.; Xu, J.; Piane, J. J.; Watson, M. P. J. Am. Chem. Soc. 2017, 139, 5313.
[32] (a) Katritzky, A. R.; Gruntz, U.; Kenny, D. H.; Rezende, M. C.; Sheikh, H. J. Chem. Soc., Perkin Trans. 11979, 430.
(b) Katritzky, A. R.; Marson, C. M. Angew. Chem., Int. Ed. 1984, 23, 420.
[33] (a) Shao, Z.; Li, X.; Chang, H.; Wei, W. Chemistry 2013, 76, 704.
(b) Dilman, A. D.; Levin, V. V. Tetrahedron Lett. 2016, 57, 3986.
[34] Xie, L. G.; Wang, Z. X. Angew. Chem., Int. Ed. 2011, 50, 4901.
[35] (a) Zhang, X.-Q.; Wang, Z.-X. J. Org. Chem. 2012, 77, 3658.
(b) Yang, X.; Wang, Z.-X. Organometallics 2014, 33, 5863.
[36] Wang, D.-Y.; Morimoto, K.; Yang, Z.-K.; Wang, C.; Uchiyama, M. Chem.-Asian J. 2017, 12, 2554.
[37] (a) Stille, J. K. Angew. Chem., Int. Ed. 1986, 25, 508.
(b) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87.
[38] Wang, D.-Y.; Kawahata, M.; Yang, Z.-K.; Miyamoto, K.; Komagawa, S.; Yamaguchi, K.; Wang, C.; Uchiyama, M. Nat. Commun. 2016, 7, 12937.
[39] Yamamura, M.; Moritani, I.; Murahashi, S.-I. J. Organomet. Chem. 1975, 91, C39.
(b) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.
(c) Giannerini, M.; Fañanás-Mastral, M.; Feringa, B. L. Nat. Chem. 2013, 5, 667.
[40] Yang, Z.-K.; Wang, D.-Y.; Minami, H.; Ogawa, H.; Ozaki, T.; Saito, T.; Miyamoto, K.; Wang, C.; Uchiyama, M. Chem.-Eur. J. 2016, 22, 15693.
[41] He, F.; Wang, Z.-X. Tetrahedron 2017, 73, 4450.
[42] Ogawa, H.; Yang, Z.-K.; Minami, H.; Kojima, K.; Saito, T.; Wang, C.; Uchiyama, M. ACS Catal. 2017, 7, 3988.
[43] Zhu, F.; Tao, J.-L.; Wang, Z.-X. Org. Lett. 2015, 17, 4926.
[44] Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X. J. Am. Chem. Soc. 2015, 137, 1623.
[45] Uemura, T.; Yamaguchi, M.; Chatani, N. Angew. Chem., Int. Ed. 2016, 55, 3162.
[46] Klauck, F. J. R.; James, M. J.; Glorius, F. Angew. Chem., Int. Ed. 2017, 56, 12336.
[47] Spettel, M.; Pollice, R.; Schnürch, M. Org. Lett. 2017, 19, 4287.
[48] (a) Hofmann, A. W. Justus Liebigs Ann. Chem. 1851, 79, 11.
(b) von Hofmann, A. W. Justus Liebigs Ann. Chem. 1851, 78, 253.
[49] Li, J. W.; Zheng, Z. J.; Xiao, T. T.; Xu, P. F.; Wei, H. Asian J. Org. Chem. 2018, 7, 133.
[50] (a) Gambarotta, S.; Alper, H. J. Organomet. Chem. 1980, 194, C19.
(b) Lei, Y.; Zhang, R.; Wu, Q.; Mei, H.; Xiao, B.; Li, G. J. Mol. Catal. A 2014, 381, 120.
(c) Lei, Y.; Zhang, R.; Wu, L.; Wu, Q.; Mei, H.; Li, G. Appl. Organomet. Chem. 2014, 28, 310.
[51] Moragas, T.; Gaydou, M.; Martin, R. Angew. Chem., Int. Ed. 2016, 55, 5053.
[52] Zhang, X.-Q.; Wang, Z.-X. Org. Bioorg. Chem. 2014, 12, 1448.
[53] Zhang, H.; Hagihara, S.; Itami, K. Chem.-Eur. J. 2015, 21, 16796.
[54] Hu, J.; Sun, H.; Cai, W.; Pu, X.; Zhang, Y.; Shi, Z. J. Org. Chem. 2016, 81, 14.
[55] Basch, C. H.; Cobb, K. M.; Watson, M. P. Org. Lett. 2016, 18, 136.
[56] Mfuh, A. M.; Doyle, J. D.; Chhetri, B.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2016, 138, 2985.
[57] (a) Said, S. A.; Fiksdahl, A. Tetrahedron:Asymmetry 2001, 12, 1947.
(b) Gui, Y.; Tian, S. K. Org. Lett. 2017, 19, 1554.
(c) Erika, B.; Istvan, G.; Gyorgy, K. Lett. Org. Chem. 2011, 8, 22.
[58] Lu, F. L.; Chen, Z. Y.; Li, Z.; Wang, X. Y.; Peng, X. Y.; Li, C.; Li, R.; Pei, H. Q.; Wang, H. M.; Gao, M. Asian J. Org. Chem. 2018, 7, 141.

过渡金属催化的基于季铵盐C-N键断裂的偶联反应研究进展

Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613.
[2]	Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.
[3]	Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704.
[4]	Wei-Yuan Ma, Huifang Dai, Shaolin Kang, Tianlin Zhang, Xing-Zhong Shu. Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3614-3622.
[5]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.
[6]	Haoru Song, Jianting Sun, Min LÜ, Yiwen Liu, Bangguo Wei. Trifluoromethyl Sulfonic Anhydride Mediated Addition of Pyridine with Ynamides [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2433-2437.
[7]	Cheng Gong, Jian Tang, Fei Xu, Pengjie Li, Zetian Wang, Yumin Zhang, Guoxian Yu, Liang Wang. Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1925-1949.
[8]	Yazhou Wang, Yuhang Zhu, Lixia Xu, Rui He, Jian Zhang. Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2000-2014.
[9]	Zhihao Zhang, Xin Jiang, Qinghan Li. Recent Progress in the Synthesis of Substituted Benzo[b]furan Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 945-964.
[10]	Hui Li, Liang Yin. Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3183-3200.
[11]	Lei Zhang, Chen Yang, Xuefeng Guo, Fanyang Mo. Research Progress of Suzuki-Miyaura Cross-Coupling Reaction Mechanism [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3492-3510.
[12]	Zhen Zhang, Wenxu Chang. Progress in Transition-Metal-Catalyzed Cyclization of Carbodiimides [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1835-1850.
[13]	Qinghan Li, Ruiqiang Luo, Chuan Wu, Hongliu Xiao, Shaopeng Guo, Zhihao Zhang, Zheyao Huang, Lin Zhou. Research Progress of Cross-Coupling Reactions of Alkylaluminums with Electrophiles Reagents [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1489-1497.
[14]	Liang Wu, Hanlin Wei, Jianzhong Chen, Wanbin Zhang. Development of Nickel-Catalyzed Cross-Coupling of Alcohol Derivatives to Construct Carbon-Carbon Bonds [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4208-4239.
[15]	Li Yaqiong, Fan Yuhang, Jia Qianfa. Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp²)-C(sp²) and C(sp²)-C(sp³) Bonds [J]. Chin. J. Org. Chem., 2019, 39(2): 350-362.