季铵盐C—N键断裂构建C—X键的研究进展

doi:10.6023/A21110536

化学学报 ›› 2022, Vol. 80 ›› Issue (3): 386-394.DOI: 10.6023/A21110536 上一篇下一篇

综述

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)

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摘要/Abstract

胺类种类繁多, 原料易得. 胺类的C—N键键能较大, 一般需要通过活化再进行断裂. 近些年发展了多种氨基的活化方法, 其中把胺类转化为季铵盐的活化方法, 制备容易、存放稳定, 具有一定优势. 最近十年左右, 芳香胺和苄胺衍生的季铵盐通过C—N键断裂、构建各种C—X键的研究取得了巨大的研究进展. 本综述主要论述了最近几年需要和不需要过渡金属催化的季铵盐通过C—N键断裂构建C—X键的反应. 通过C—N键断裂, 季铵盐可以构建C—B键、C—C键、C—N键、C—O键、C—Si键、C—P键、C—S键、C—Se键等, 合成硼酸酯、芳烃、烷烃、醚类、胺类、硅烷、膦、硫醚、二硫化物、硒醚、二硒化物等化合物. 而且, 如果是采用手性苄胺衍生的季铵盐, 还可以得到多种高对映体纯的手性有机化合物; 季铵盐的手性在产物中保持良好, 并且, 对所有反应都发生S_N2型的构型翻转.

关键词: 胺类, 季铵盐, C—N键断裂, C—X键偶联, 手性保留

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

引用此文

王一丁, 李福海, 曾庆乐. 季铵盐C—N键断裂构建C—X键的研究进展[J]. 化学学报, 2022, 80(3): 386-394.

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.

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图/表 21

图1. 金属催化季铵盐与格氏试剂的C—N键断裂/C—C键偶联反应

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

图2. 过渡金属催化季铵盐与有机金属试剂的偶联反应

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

图3. 过渡金属催化季铵盐参与的Suzuki偶联反应及镍催化的机理推测

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

图4. 过渡金属催化季铵盐与端炔的偶联反应

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

图5. 钯催化芳基季铵盐与杂环的C—N键断裂/C—C偶联反应及其机理

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

图6. 过渡金属催化季铵盐与芳基硅烷的Hiyama交叉偶联反应及推测的钯催化反应机理

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

图7. 过渡金属催化季铵盐与CO2和CO的反应

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

图8. 过渡金属催化季铵盐与有机硅试剂生成C—Si键的反应

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

图9. 过渡金属催化季铵盐参与的C—N交叉偶联反应

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

图10. 过渡金属催化季铵盐与二烃基氧膦的交叉偶联反应

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

图11. 铜催化苄基季铵盐的C—N键断裂/C—S键偶联反应合成手性苄基硫醚

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

图12. 铜催化季铵盐和烷基二硫代氨基甲酸盐、烃基亚磺酸钠的 C—N键断裂/C—S键偶联反应

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

图13. 过渡金属催化季铵盐的C—N键断裂/C—B键偶联反应

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

图14. 苯炔与叔胺原位形成的季铵盐参与构建多种C—X键

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

图15. 二芳基二硫化物、二硒化物和季铵盐反应合成高对映体纯的手性苄基硫醚、手性苄基硒醚

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

图16. 硫化钠、二硫化二钠和季铵盐的SN2亲核取代反应合成高对映体纯的手性苄基硫醚

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

图17. 硒单质和季铵盐反应合成高对映体纯的手性苄基硒醚

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

图18. 碱性条件下烃基亚磺酰基负离子等价物与(手性)苄基季铵盐的脱氧/C—S键偶联反应

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

图19. 光诱导季铵盐与四羟基二硼或二硼酸酯反应生成芳基硼酸(酯)

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

图20. 芳基铵盐参与的多种C—X键形成反应

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

图21. 苄基季铵盐和二氧化碳的直接电化学羰基化反应

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

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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

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