Advances in Formation of C—X Bonds via Cleavage of C—N Bond of Quaternary Ammonium Salts

doi:10.6023/A21110536

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (3): 386-394.DOI: 10.6023/A21110536 Previous Articles Next Articles

Review

季铵盐C—N键断裂构建C—X键的研究进展

王一丁, 李福海, 曾庆乐^*()

成都理工大学地质灾害防治与地质环境保护国家重点实验室材料与化学化工学院成都 610059

投稿日期:2021-11-27 发布日期:2021-12-16
通讯作者: 曾庆乐

作者简介:

王一丁, 成都理工大学2019 级硕士生. 本科毕业于成都理工大学, 硕士阶段师从曾庆乐教授, 主要从事钯催化环化反应和不对称催化反应.

李福海, 成都理工大学2018级硕士生, 本科毕业于四川理工学院(今更名为四川轻化工大学), 硕士阶段师从曾庆乐教授, 主要从事有机合成方法学和有机硒化学的研究.

曾庆乐, 教授, 博士生导师, 四川省有突出贡献的优秀专家, 1970年出生于福建省漳州市平和县, 1994年在福建师范大学获得理学学士学位, 1997年在中国科学院兰州化学物理研究所获得理学硕士学位, 2002年在中国科学院成都有机化学研究所获得理学博士学位. 2006年5月入职成都理工大学. 2008年至2009年在美国麻省理工学院做访问科学家. 主要研究方向包括有机合成方法学、(手性)有机硫化学、矿产资源化学和环境治理材料.

^† 共同第一作者

基金资助:
国家自然科学基金(20672088); 国家自然科学基金(21372034); 成都市科技局(2019-YF05-02395-SN); 地质灾害防治与地质环境保护国家重点实验室(SKLGP2020Z003)

Advances in Formation of C—X Bonds via Cleavage of C—N Bond of Quaternary Ammonium Salts

Yiding Wang, Fuhai Li, Qingle Zeng()

State Key Laboratory of Geohazard Prevention and Geoenvironment Protection, College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, China

Received:2021-11-27 Published:2021-12-16
Contact: Qingle Zeng
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(20672088); National Natural Science Foundation of China(21372034); Chengdu Science and Technology Bureau(2019-YF05-02395-SN); State Key Laboratory of Geohazard Prevention and Geoenvironment Protection(SKLGP2020Z003)

Amines have a wide variety and are readily available. Due to the larger C—N bond energy of amines, C—N bond of amines generally needs to be activated before cleavage. In recent years, a variety of activation methods of amino groups have been developed. Among the activation methods, converting amines into quaternary ammonium salts has certain advantages of easy preparation and stable storage. In last decade, quaternary ammonium salts derived from aromatic amines and benzylamines have made great progress in the study of constructing various C—X bonds via cleavage of C—N bond. This review mainly discusses the formation of C—X bonds of quaternary ammonium salts via cleavage of C—N bond with or without transition metal catalysts over the past few years. Via C—N bond breakage, quaternary ammonium salts can construct C—B bond, C—C bond, C—N bond, C—O bond, C—Si bond, C—P bond, C—S bond, C—Se bond, and so on. And thus borates, aromatics, alkanes, ethers, amines, silanes, phosphines, thioethers, disulfides, selenoethers, diselenides and other compounds are synthesized. Moreover, if the quaternary ammonium salts derived from chiral benzylamines are adopted, a variety of highly enantiopure chiral organic compounds are obtained. The chiralities of quaternary ammonium salts are excellently kept in the products, and S_N2 type configuration reversal occurs for all of the reported reactions.

Key words: amines, quaternary ammonium salts, cleavage of C—N bond, C—X bond coupling reaction, chiral retention

Cite this article

Yiding Wang, Fuhai Li, Qingle Zeng. Advances in Formation of C—X Bonds via Cleavage of C—N Bond of Quaternary Ammonium Salts[J]. Acta Chimica Sinica, 2022, 80(3): 386-394.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 21

Figure 1. Metal catalyzed C—N bond breakage/C—C bond coupling reactions between quaternary ammonium salts and Grignard reagents

Figure 2. Transition metal catalyzed coupling reactions of quaternary ammonium salts with organometallic reagents

Figure 3. Transition metal catalyzed Suzuki coupling reactions with quaternary ammonium salts and mechanism speculation of nickel catalysis

Figure 4. Transition metal catalyzed coupling reactions of quaternary ammonium salts with terminal alkynes

Figure 5. Palladium catalyzed C—N bond breaking/C—C coupling reaction mechanism of aryl quaternary ammonium salts with heterocycles

Figure 6. Transition metal catalyzed Hiyama cross coupling reactions between quaternary ammonium salts and arylsilanes and the speculated mechanism of the palladium catalyzed reaction

Figure 7. Reaction of quaternary ammonium salts with CO2 and CO catalyzed by transition metal

Figure 8. Transition metal catalyzed formation of C—Si bond of quaternary ammonium salts and organosilicon reagents

Figure 9. Transition metal catalyzed C—N cross coupling reactions with quaternary ammonium salts

Figure 10. Transition metal catalyzed cross coupling reactions of quaternary ammonium salts with dialkyl/diaryl phosphine oxides

Figure 11. Copper catalyzed C—N bond breaking/C—S bond coupling reaction of benzyl quaternary ammonium salts to synthesize chiral benzyl thioethers

Figure 12. Copper catalyzed cleavage of C—N bond/C—S bond coupling reactions of quaternary ammonium salts, alkyl dithiocarbamates and sodium alkyl/arylsulfinates

Figure 13. Transition metal catalyzed cleavage of C—N bond/C—B bond coupling reactions of quaternary ammonium salts

Figure 14. Quaternary ammonium salts formed in situ from benzyne and tertiary amines to participate in the construction of various C—X bonds

Figure 15. Synthesis of highly enantiopure chiral benzyl thioethers and chiral benzyl selenoethers by reactions of diaryl disulfides, diselenides and quaternary ammonium salts

Figure 16. Synthesis of highly enantiopure chiral benzyl thioethers by SN2 nucleophilic substitution of Na2S and Na2S2 with quaternary ammonium salts

Figure 17. Synthesis of highly enantiopure chiral benzyl selenoethers by reaction of elemental selenium with quaternary ammonium salts

Figure 18. Deoxygenation/C—S bond coupling reaction of aryl/xalkylsulfinyl anion surrogates with (chiral) benzylic quaternary ammonium salts under alkaline condition

Figure 19. Photoinduced reaction of quaternary ammonium salts and tetrahydroxydiboron or diboronic esters to produce arylboric acids or esters

Figure 20. Multiple C—X bond formation reactions involving arylammonium salts

Figure 21. Direct electrochemical carboxylation of benzylic quaternary ammonium salts with carbon dioxide

References 59

[1]	Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852. doi: 10.1021/ar970282g
[2]	Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400. doi: 10.1002/(ISSN)1521-3773
[3]	Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599. doi: 10.1002/adsc.200404216
[4]	Ouyang, K.; Hao, W.; Zhang, W. X.; Xi, Z. Chem. Rev. 2015, 115, 12045. doi: 10.1021/acs.chemrev.5b00386
[5]	Wang, Q.; Su, Y.; Li, L.; Huang, H. Chem. Soc. Rev. 2016, 45, 1257. doi: 10.1039/C5CS00534E
[6]	Wang, Z. X.; Yang, B. Org. Biomol. Chem. 2020, 18, 1057. doi: 10.1039/C9OB02667C
[7]	Li, G.; Chen, Y.; Xia, J. B. Chin. J. Org. Chem. 2018, 38, 1949. (in Chinese) doi: 10.6023/cjoc201803013
	(李刚, 陈烨, 夏纪宝, 有机化学, 2018, 38, 1949.) doi: 10.6023/cjoc201803013
[8]	Song, M. M.; Zhang, Z. G.; Zheng, D.; Li, X.; Liang, R.; Zhao, X. N.; Shi, L.; Zhang, G. S. Chin. J. Org. Chem. 2020, 40, 2433. (in Chinese) doi: 10.6023/cjoc202001007
	(宋蒙蒙, 张志国, 郑丹, 李祥, 梁蕊, 赵旭娜, 时蕾, 张贵生, 有机化学, 2020, 40, 2433.) doi: 10.6023/cjoc202001007
[9]	Menggen, Q.; Wu, Y.; Bao, Y. S. Chin. J. Org. Chem. 2018, 38, 902. (in Chinese)
	(孟根其其格, 乌云, 包永胜, 有机化学, 2018, 38, 902.) doi: 10.6023/cjoc201710034
[10]	Zhao, Y.; Li, S. H.; Zhang, M. M.; Liu, F. Acta Chim. Sinica 2019, 77, 916. (in Chinese) doi: 10.6023/A19040121
	(赵勇, 李施宏, 张苗苗, 刘峰, 化学学报, 2019, 77, 916.) doi: 10.6023/A19040121
[11]	Liu, J.; Yang, Y.; Ouyang, K.; Zhang, W. X. Green Synth. Catal. 2021, 2, 87.
[12]	Wang, C. Chem. Pharm. Bull. 2020, 68, 683. doi: 10.1248/cpb.c20-00196
[13]	Bao, H.; Qi, X.; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 1206. doi: 10.1021/ja110500m
[14]	Wenkert, E.; Han, A. L.; Jenny, C. J. J. Chem. Soc. Chem. Commnu. 1988, 975.
[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. doi: 10.1021/ol1018739
[16]	Guo, W. J.; Wang, Z. X. Tetrahedron 2013, 69, 9580. doi: 10.1016/j.tet.2013.09.039
[17]	Xie, L. G.; Wang, Z. X. Angew. Chem. Int. Ed. 2011, 50, 4901. doi: 10.1002/anie.v50.21
[18]	Ogawa, H.; Yang, Z. K.; Minami, H.; Kojima, K.; Saito, T.; Wang, C.; Uchiyama, M. ACS Catal. 2017, 7, 3988. doi: 10.1021/acscatal.7b01058
[19]	Wang, D. Y.; Kawahata, M.; Yang, Z. K.; Miyamoto, K.; Komagawa, S.; Yamaguchi, K.; Wang, C.; Uchiyama, M. Nature Commun. 2016, 7, 12937. doi: 10.1038/ncomms12937
[20]	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. doi: 10.1002/chem.201603436
[21]	Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046. pmid: 12785821
[22]	Maity, P.; Shacklady-McAtee, D. M.; Yap, G. P. A.; Sirianni, E. R.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 280. doi: 10.1021/ja3089422
[23]	Chen, Q.; Gao, F.; Tang, H.; Yao, M.; Zhao, Q.; Shi, Y.; Dang, Y.; Cao, C. ACS Catal. 2019, 9, 3730. doi: 10.1021/acscatal.9b00218
[24]	Xu, S.; Zhang, Z.; Han, C.; Hu, W.; Xiao, T.; Yuan, Y.; Zhao, J. J. Org. Chem. 2019, 84, 12192. doi: 10.1021/acs.joc.9b01877
[25]	Zhu, F.; Tao, J. L.; Wang, Z. X. Org. Lett. 2015, 17, 4926. doi: 10.1021/acs.orglett.5b02458
[26]	Han, C.; Zhang, Z.; Xu, S.; Wang, K.; Chen, K.; Zhao, J. J. Org. Chem. 2019, 84, 16308. doi: 10.1021/acs.joc.9b02554
[27]	Moragas, T.; Gaydou, M.; Martin, R. Angew. Chem. Int. Ed. 2016, 55, 5053. doi: 10.1002/anie.v55.16
[28]	Liao, L. L.; Cao, G. M.; Ye, J. H.; Sun, G. Q.; Zhou, W. J.; Gui, Y. Y.; Yan, S. S.; Shen, G.; Yu, D. G. J. Am. Chem. Soc. 2018, 140, 17338. doi: 10.1021/jacs.8b08792 pmid: 30518213
[29]	Yu, W.; Yang, S.; Xiong, F.; Fan, T.; Feng, Y.; Huang, Y.; Fu, J.; Wang, T. Org. Biomol. Chem. 2018, 16, 3099. doi: 10.1039/C8OB00488A
[30]	Rand Alexander, W.; Montgomery, J. Chem. Sci. 2019, 10, 5338. doi: 10.1039/c9sc01083a pmid: 31191891
[31]	Scharfbier, J.; Gross, B. M.; Oestreich, M. Angew. Chem. Int. Ed. 2020, 59, 1577. doi: 10.1002/anie.v59.4
[32]	Zhang, X. Q.; Wang, Z. X. Org. Biomol. Chem. 2014, 12, 1448. doi: 10.1039/c3ob41989d
[33]	Chen, H.; Yang, H.; Li, N.; Xue, X.; He, Z.; Zeng, Q. Org. Proc. Res. Dev. 2019, 23, 1679.
[34]	Yang, B.; Wang, Z. X. J. Org. Chem. 2019, 84, 1500. doi: 10.1021/acs.joc.8b02926 pmid: 30628791
[35]	Li, N.; Chen, F.; Wang, G.; Zeng, Q. Monatsch. Chem. 2020, 151, 99. doi: 10.1007/s00706-019-02535-y
[36]	O'Connor, S. E.; Grosset, A.; Janiak, P. Fund. Clin. Pharmacol. 1999, 13, 145. pmid: 10226758
[37]	Sobal, G.; Menzel, E. J.; Sinzinger, H. Biochem. Pharmacol. 2001, 61, 373. pmid: 11172743
[38]	Zeng, Q.; Wang, H.; Wang, T.; Cai, Y.; Weng, W.; Zhao, Y. Adv. Synth. Catal. 2005, 347, 1933. doi: 10.1002/(ISSN)1615-4169
[39]	Zhang, L.; Tan, M.; Zhou, L.; Zeng, Q. Tetrahedron Lett. 2018, 59, 2778. doi: 10.1016/j.tetlet.2018.06.008
[40]	Jiang, W.; Huang, Y.; Zhou, L.; Zeng, Q. Sci. China Chem. 2019, 62, 1213. doi: 10.1007/s11426-019-9499-5
[41]	Feng, J.; Zhang, Q.; Li, F.; Yang, L.; Kuchukulla, R. R.; Zeng, Q. Synlett 2021, 32, 224. doi: 10.1055/s-0040-1707319
[42]	Jiang, W.; Li, N.; Zhou, L.; Zeng, Q. ACS Catal. 2018, 8, 9899. doi: 10.1021/acscatal.8b03032
[43]	Chen, H.; Jiang, W.; Zeng, Q. Chem. Rec. 2020, 20, 1269. doi: 10.1002/tcr.v20.11
[44]	Chen, H.; Zhang, Q.; Zheng, W.; Yang, H.; Zeng, Q. Asian J. Org. Chem. 2020, 9, 773. doi: 10.1002/ajoc.v9.5
[45]	Huang, Y.; Chen, H.; Zheng, W.; Zeng, Q. Tetrahedron Lett. 2020, 61, 152320. doi: 10.1016/j.tetlet.2020.152320
[46]	Huang, Y.; Li, J.; Chen, H.; He, Z.; Zeng, Q. Chem. Rec. 2021, 21, 1216. doi: 10.1002/tcr.v21.5
[47]	Zhang, H.; Hagihara, S.; Itami, K. Chem. Eur. J. 2015, 21, 16796. doi: 10.1002/chem.v21.47
[48]	Hu, J.; Sun, H.; Cai, W.; Pu, X.; Zhang, Y.; Shi, Z. J. Org. Chem. 2016, 81, 14. doi: 10.1021/acs.joc.5b02557
[49]	Basch, C. H.; Cobb, K. M.; Watson, M. P. Org. Lett. 2016, 18, 136. doi: 10.1021/acs.orglett.5b03455
[50]	Gui, Y.; Tian, S. K. Org. Lett. 2017, 19, 1554. doi: 10.1021/acs.orglett.7b00365
[51]	Li, F.; Wang, D.; Chen, H.; He, Z.; Zhou, L.; Zeng, Q. Chem. Commun. 2020, 56, 13029. doi: 10.1039/D0CC05633B
[52]	Tang, Q.; Li, F.; Chen, F.; Yin, X.; Tang, Y.; Zeng, Q. Asian J. Org. Chem. 2021, 10, 1687. doi: 10.1002/ajoc.v10.7
[53]	Chen, F.; Li, F.; Zeng, Q. Eur. J. Org. Chem. 2021, 2021, 5605. doi: 10.1002/ejoc.v2021.41
[54]	Zhang, Q.; Feng, H.; Yang, H.; He, Z.; Zeng, Q. J. Org. Chem. 2021, 86, 7806. doi: 10.1021/acs.joc.1c00615
[55]	Yang, L.; Wang, B.; Yin, X.; Zeng, Q. Chem. Rec. 2021, DOI: 10.1002/tcr.202100242. doi: 10.1002/tcr.202100242
[56]	Mfuh, A. M.; Doyle, J. D.; Chhetri, B.; Arman, H. D.; Larionov, O. V. J. Am. Chem. Soc. 2016, 138, 2985. doi: 10.1021/jacs.6b01376
[57]	Wang, D. Y.; Yang, Z. K.; Wang, C.; Zhang, A.; Uchiyama, M. Angew. Chem. Int. Ed. 2018, 57, 3641. doi: 10.1002/anie.201712618
[58]	Wang, D. Y.; Wen, X.; Xiong, C. D.; Zhao, J. N.; Ding, C. Y.; Meng, Q.; Zhou, H.; Wang, C.; Uchiyama, M.; Lu, X. J.; Zhang, A. iScience 2019, 15, 307. doi: 10.1016/j.isci.2019.04.038
[59]	Yang, D. T.; Zhu, M.; Schiffer, Z. J.; Williams, K.; Song, X.; Liu, X.; Manthiram, K. ACS Catal. 2019, 9, 4699. doi: 10.1021/acscatal.9b00818

季铵盐C—N键断裂构建C—X键的研究进展

Advances in Formation of C—X Bonds via Cleavage of C—N Bond of Quaternary Ammonium Salts

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 21

References 59

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Liu Ruxue, He Xiaoyan, Niu Litong, Lv Bolin, Yu Fei, Zhang Zhe, Yang Zhiwang. Hierarchical In₂S₃/CdIn₂S₄ Heterostructured Nanohybrids as Photocatalyst for Coupling of Benzyl Amines under Visible Light [J]. Acta Chim. Sinica, 2019, 77(7): 653-660.
[2]	Zhang Zhaoxiang, Liu Yujie, Wang Qi, Wang Jingjing. Capillary Electrophoresis and Quantum Dot Electrochemiluminescence by Micellar Reversed Sweeping [J]. Acta Chim. Sinica, 2019, 77(2): 179-183.
[3]	Li Xuefei, Chen Ling, Xu Shengchao, Zhao Wenbo. Liquid-liquid Phase-change Absorption of SO₂ Using N,N-Dimethyl-n-octylamine Mixed with Hexadecane [J]. Acta Chimica Sinica, 2019, 77(12): 1287-1293.
[4]	Zhang Yongling, Wang Min, Cao Peng, Liao Jian. Copper-Catalyzed Enantioselective Aminoboration of Styrenes with Chiral Sulfoxide Phosphine Ligand [J]. Acta Chim. Sinica, 2017, 75(8): 794-797.
[5]	Zhang Binbin, Zhan Dan, Zhang Xiaoping, Xiang Qinjie, Zeng Qingle. Ligand-free Pd-Catalyzed C—N Coupling of Diphenylamine and Aryl Halides under Air [J]. Acta Chimica Sinica, 2012, 70(15): 1655-1659.
[6]	ZHOU Xin, SHANG Jia, LIU Ming-Ming, LIU Han-Lan, HAO Rong, FENG Xiong-Han, LIU Fan. Preparation of Novel Ionic Liquids-Based Sol-Gel Coatings for Solid-Phase Microextraction [J]. Acta Chimica Sinica, 2010, 68(17): 1749-1757.
[7]	. Synthesis and Spectrum Stability of an Oligomeric Terfluorene Tethered with Antioxidant Hindered Amine [J]. Acta Chimica Sinica, 2008, 26(23): 2575-2578.
[8]	WANG Gui-Xiang; XIAO He-Ming*; JU Xue-Hai; GONG Xue-Dong. Theoretical Studies on Densities, Detonation Velocities and Pres-sures and Electric Spark Sensitivities of Energetic Materials [J]. Acta Chimica Sinica, 2007, 65(6): 517-524.
[9]	Liu Hongmin;Zhang Fuyi;Xu Wen;Li Shi. Synthesis of Aminosugars Having New Structures from Oxosugars [J]. Acta Chimica Sinica, 2003, 61(7): 1149-1152.
[10]	Yuan Qiaolong;Wang Dening;Wu Shusen;Ying Shengkang. Adsorption of Poly(urethane-urea-amine) Acetate on Colloidal Silica [J]. Acta Chimica Sinica, 2003, 61(10): 1543-1549.
[11]	Gao Xiang;Zhang Xiaoyue;Zhang Danwei;Liu Ying;Wu Shihui. A Thermoinduced [3+2] Cycloaddition of Allylic Amines with C_(60) [J]. Acta Chimica Sinica, 2003, 61(10): 1686-1691.
[12]	Sun Xiaoling;Li Xingya;Jiang Xikui;Fu Wimin. Novel Reactions of Enamines with Perhaloethanes: A Facile Route to β-CF_3 Substituted α, β-Unsaturated Ketones [J]. Acta Chimica Sinica, 2003, 61(10): 1641-1645.
[13]	Song Maoying;Wang Xiqing;Qian Bin;Zeng Yu;Long Yingcai. Studies on Properties of Pure-silica β Zeolite [J]. Acta Chimica Sinica, 2002, 60(3): 451-456.
[14]	Guo Gangjun;Ma lin;Mao Xuepu;Gu Lianquan;Wang Jun. A Novel Arylamine-o-quinone Polymer: Synthesis and Application as a Nano-support for Immobilized Enzymes [J]. Acta Chimica Sinica, 2002, 60(3): 499-503.
[15]	Shi Feng;Deng Youquan. Synthesis of alkylformamide catalyzed by organic Au(Ⅰ) complexes [J]. Acta Chimica Sinica, 2001, 59(6): 979-981.