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化学进展 2024, Vol. 36 Issue (3): 401-415 DOI: 10.7536/PC230711 前一篇   后一篇

• 综述 •

球磨-点击化学反应：无溶剂绿色反应方式

关歆琪, 桑远, 刘海玲*()   

  1. 辽宁石油化工大学 抚顺 113001
  • 收稿日期:2023-07-17 修回日期:2023-09-15 出版日期:2024-03-24 发布日期:2024-02-26
  • 作者简介:

    刘海玲 博士，教授，硕士生导师。主持国家自然科学基金，入选辽宁省“兴辽英才”青年拔尖人才。在Macromolecules, ACS sustainable Chemistry & Engineering等杂志发表论文十余篇。主要研究方向为机械化学、木质素基高分子的绿色合成及改性、生物质应用于功能性材料的制备。

  • 基金资助:
    国家自然科学基金项目(52103005); 辽宁省“兴辽英才”-青年拔尖人才(XLYC2203072); 辽宁石油化工大学博士启动资金(2021XJJL-003)
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Ball-Milled Click Chemistry: A Solvent-Free Green Chemistry

Xinqi Guan, Yuan Sang, Hailing Liu()   

  1. Liaoning Petrochemical University, Fushun 113001, China
  • Received:2023-07-17 Revised:2023-09-15 Online:2024-03-24 Published:2024-02-26
  • Contact: * e-mail: HL2490053@outlook.com
  • About author:
    † These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(52103005); Liaoning Revitalization Talents Program(XLYC2203072); startup funding of Liaoning Petrochemical University(2021XJJL-003)

点击化学因反应简单、选择性高、产物单一、且无有害副产物的优点被广泛使用。作为诺贝尔化学奖项，点击化学最初被设计用于水相或绿色有机溶剂。然而在实际应用中，受限于反应物溶解性，点击化学常在极性高的有毒溶剂中进行。溶剂的使用不仅违背了绿色化学的初衷，还增加了生产成本。为了解决这些问题，球磨引起的机械化学被用来实现点击化学反应。机械化学作为一种新型的反应方式，无需溶剂。球磨-点击化学反应具有额外的优点，例如缩短反应时间、降低反应温度、减少催化剂的使用等。本文通过综述整理，报道了球磨条件下点击化学反应的研究进展，包括CuAAc、Diels-Alder、胺-异硫氰酸酯反应、胺-硫醇反应和氧氮自由基偶联反应。为了给读者提供实际操作的指导，本文也包含了球磨机选择指南，液体/固体辅助研磨物质的加入，以及影响反应转化率因素的探究，包括催化剂的选择、添加剂的加入、研磨球大小的选择、化学计量学的探讨、和球磨时间的影响。

关键词： 球磨反应, 点击化学, 机械化学, CuAAc反应, Diels-Alder反应, 胺-异硫氰酸酯, 胺-硫醇反应, 氧氮自由基偶联反应

Click chemistry won the Noble Prize in 2022 due to easy synthesis, high selectivity, single product, and no toxic side product. Click chemistry was originally designed as green chemistry to work in aqueous solutions or environmentally friendly organic solvents. However, due to the poor solubility of reactants, polar and toxic solvents are usually required to use. The solvent used violates the concept of green chemistry, as well as increases the cost. These issues hinder click chemistry to be a state-of-art green chemistry. One of the solutions to optimize click chemistry is to avoid using any solvent. Herein, ball-milled mechanochemistry does not limit reactants’ solubility and could avoid solvent use. Ball-milled mechanochemistry is a new kind of chemical reaction that is conducted in a ball mill, is induced by mechanical force, and needs no solvent or a minimal amount of solvent. As a new way of organic synthesis, ball-milled mechanochemistry could easily achieve the low-energy carbon-heteroatom bonds, which constitute the linkages in click chemistry. Therefore, it could integrate with click chemistry and achieves ball-milled click chemistry. In comparison to traditional solution click chemistry, ball-milled click chemistry avoids solvent use. Moreover, it is even superior in the ways that the reaction time is shortened, the reaction temperature is lowered, and the catalyst used is simplified. In this review, ball-milled click chemistry examples are reported as much as the authors can find, including CuAAc, Diels-Alder, amine and isothiocyanate reactions, amine thiol reactions, and nitroxide radical coupling reactions. To provide readers with a better ball-milled click chemistry manual, this paper also contains ball mill machine choice guidance, liquid-assisted grinding choice guidance, and factors impacting ball-milled click chemistry conversion, including catalyst choice, additive choice, ball choice, stoichiometry, and milling time.

Contents

1 Introduction

1.1 Ball mill machines

1.2 Liquid/solid assisted grinding

2 Ball-milled click chemistry

2.1 Ball-milled CuAAc

2.2 Ball-milled Diels-Alder

2.3 Ball-milled amine and isothiocyanate reactions

2.4 Ball-milled amine thiol reactions

2.5 Ball-milled nitroxide radical coupling reactions

3 Factors impacting ball-milled click chemistry

3.1 Catalysts

3.2 Milling balls

3.3 Additive

3.4 Stoichiometry

3.5 Reaction time

4 Conclusion and outlook

Key words: ball mill, click chemistry, mechanochemistry, CuAAc, Diels-Alder, amine and isothiocyanate reaction, amine thiol reaction, nitroxide radical coupling reaction
()
图1 球磨机照片：震动球磨机(a)，行星球磨机(b)，搅拌球磨机(c)，滚筒球磨机(d)
Fig. 1 Photos of ball mill machines: mixer ball mill (a); planetary ball mill (b); stir ball mill (c); and roller ball mill (d)
表1 震动球磨机、行星球磨机和搅拌球磨机适用情况
Table 1 Introduction of mixer ball mill, planetary ball mill, and stir ball mill
Mixer ball mill Planetary ball mill Stir Ball mill
Mechanical force Impact force Shear force -
Common Brand Retsch Fritsch Outotec HIGMill
Invented time 1923 1961 1922
Scale grams 10~100 grams More than a ton
Application Inorganic chemistry, organic chemistry Organic Chemistry Physical grinding
图式1 2011年首次发表的球磨实现的CuAAc反应[55]
Scheme 1 First published ball-milled CuAAc reaction in 2011[55]
图式2 铜粉催化球磨-CuAAc反应并应用于环糊精[56]
Scheme 2 Ball-milled copper powder catalyzed CuAAc reaction and its application in cyclodextrin[56]
图式3 球磨-CuAAc反应被三种价态铜催化剂催化[57]
Scheme 3 Ball-milled CuAAc reaction catalyzed by Cu, Cu+, and Cu2+[57]
表2 球磨-CuAAc反应与溶液-CuAAc产率对比
Table 2 Yields from Ball-milled CuAAc versus CuAAc in solution reaction
Product Catalyst Yields from solution reaction[%]a Yields from ball mill[%]b
Cu(OAc)2 21 57
CuI 5 85
Cu(OAc)2 45 60
CuI 40 87
Cu(OAc)2 89 77
CuI 52 92
Cu(OAc)2 10 72
CuI 5 79
图式4 铜罐铜球实现的一锅法球磨-CuAAc[58]
Scheme 4 One pot CuAAc milled by copper balls in copper vial[58]
图式5 Cu/Al2O3催化的一锅法球磨-CuAAc反应[59]
Scheme 5 Ball-milled one pot CuAAc reaction catalyzed by Cu/Al2O3[59]
图式6 球磨-CuAAc反应制备奎宁-三唑分子骨架的杂化抗原生动物化合物[60]
Scheme 6 Ball-milled CuAAc synthesizing quinine-triazole scaffold with antiprotozoal potency[60]
图式7 球磨-CuAAc反应制备金属缓蚀剂[61]
Scheme 7 Ball-milled CuAAc reaction synthesizing metal corrosion inhibitor[61]
图式8 球磨-CuAAc反应制备葡萄糖醛酸糖树状分子[62]
Scheme 8 Ball-milled CuAAc reaction synthesizing glucuronic acid glycodendrimers[62]
图式9 球磨实现的Diels-Alder反应[67]
Scheme 9 Ball-milled Diels-Alder reaction[67]
图式10 三氯化铁催化的苯乙烯与氮-芳香亚胺球磨- Diels-Alder反应[68]
Scheme 10 Ball-milled Diels-Alder reaction between styrene and N-aryl aldimines promoted by FeCl3[68]
图式11 球磨实现的Diels-Alder反应应用于冠状物改性[69]
Scheme 11 Ball-milled Diels-Alder reaction in rotaxane modification[69]
图式12 球磨实现的Diels-Alder反应应用于石墨烯制备[70]
Scheme 12 Ball-milled Diels-Alder reaction in synthesizing graphene[70]
图式13 球磨实现的Diels-Alder反应应用于功能化石墨烯制备[71]
Scheme 13 Ball-milled Diels-Alder reaction in synthesizing functioned graphene[71]
图式14 球磨实现的Diels-Alder反应湿法制备石墨烯
Scheme 14 Ball-milled Diels-Alder reaction in wet-synthesizing graphene[72]
图式15 球磨实现的胺-异硫氰酸酯反应制备硫脲[91??~94]
Scheme 15 Ball-milled amines and isothiocyanates synthesizing thiourea[91??~94]
图式16 球磨实现的胺-硫醇反应[95]
Scheme 16 Ball-milled amine?thiol scrambling[95]
图式17 球磨实现的氧氮自由基偶联反应[98]
Scheme 17 Ball-milled nitroxide radical coupling reactions[98]
表3 醋酸铜、碘化铜、黄铜球的催化下，球磨CuAAc的反应产率
Table 3 Ball-milled CuAAc yields catalyzed by Cu(OAc)2, CuI, or brass ball
Product Catalyst Yields[%]
Cu(OAc)2a 57
CuIb 85
Brass ballc 77
Cu(OAc)2a 60
CuIb 87
Brass ballc 80
Cu(OAc)2a 77
CuIb 92
Brass ballc 87
Cu(OAc)2a 72
CuIb 79
Brass ballc 76
表4 一锅法球磨CuAAc在不定量的催化剂下的产率
Table 4 One pot ball-milled CuAAc yields under varied catalyst dose
Number Catalyst amount (mol%) Yields(%)
1 0 0
2 2 51
3 5 72
4 10 96
表5 球磨Diels-Alder反应中Lewis酸和Bronsted酸催化剂对产率的影响
Table 5 Ball-milled Diels-Alder reaction yields catalyzed by Lewis acids or Bronsted acids
Number Catalyst Yields(%)
1 ZnCl2 76
2 AlCl3 85
3 CuCl2 15
4 FeCl3 86
5 Cu(OAc)2 10
6 Co(OAc)2 Not detected
7 Mn(OAc)2 Trace
8 Pd(OAc)2 Trace
9 BF3·OEt2 81
10 Cu(OTf)2 56
11 TFA 48
12 p-TsOH 12
13 KHSO4 Trace
14 KH2PO4 Not detected
表6 相同总质量，不同大小和数量研磨球对反应的影响
Table 6 Yields from different mill balls in terms of sizes and numbers
Number Ball numbers Effective surface area a(mm2) Yields (%)
2mm Ø 5mm Ø 10mm Ø
1 0 0 10 10666 67
2 625 0 10 18520 80
3 1500 48 0 30144 99
表7 一锅法球磨CuAAC在不定量K2CO3添加剂下的产率
Table 7 One pot ball-milled CuAAC yields with varied K2CO3 additives
Number K2CO3(equivalent) Yields(%)
1 0 52
2 1 91
3 3 90
表8 球磨CuAAc中试剂比例对产率的影响
Table 8 Ball-milled CuAAc yields impact by stoichiometric ratio
Number Stoichiometry
a:b:CuSO4·H2O:NaAsc		 Reaction time Conversion（%）
1 0.5:1.1:0.2:0.35 9 54
2 0.5:1.65:0.3:0.53 9 61
3 0.5:2.5:0.3:0.53 11 65
4 0.5:3.5:0.4:0.7 11 >99
表9 一锅法球磨CuAAc在不同反应时间下的产率
Table 9 One pot ball-milled CuAAc yields under varied reaction time
Number Time (min) Yields (%)
1 30 62
2 45 80
3 60 96
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