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化学进展 2022, Vol. 34 Issue (10): 2134-2145 DOI: 10.7536/PC220103 前一篇   后一篇

• 综述与评论 •

环张力促进的叠氮-炔环加成反应

廖伊铭1, 吴宝琪1, 唐荣志2,*(), 林峰1, 谭余1,*()   

  1. 1 中山大学化学工程与技术学院 珠海 519082
    2 香港城市大学能源与环境学院 香港 999077
  • 修回日期:2022-01-27 出版日期:2022-10-24 发布日期:2022-04-01
  • 通讯作者: 唐荣志, 谭余
  • 作者简介:

    谭余 2016年博士毕业于复旦大学,研究方向为有机合成。2016—2019年在麻省大学医学院作为博士后从事生物医用水凝胶方向的研究。2019—2020年在美国西北大学作为博士后从事超分子化学的研究。目前为中山大学百人计划副教授,从事水凝胶和超分子化学在海洋化工中的应用研究。

  • 基金资助:
    中山大学百人计划启动经费(76110-18841290); 中山大学大学生创新创业训练计划项目(20211956)
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Strain-Promoted Azide-Alkyne Cycloaddition

Liao Yiming1, Wu Baoqi1, Tang Rongzhi2(), Lin Feng1, Tan Yu1()   

  1. 1 School of Chemical Engineering and Technology, Sun Yat-Sen University,Zhuhai 519082, China
    2 School of Energy and Environment, City University of Hong Kong, Hong Kong 999077, China
  • Revised:2022-01-27 Online:2022-10-24 Published:2022-04-01
  • Contact: Tang Rongzhi, Tan Yu
  • Supported by:
    Start-up Fund(76110-18841290); Innovation and Entrepreneurship Training Program for College Students of Sun Yat-sen University(20211956)

近年来,点击化学中的环张力促进的叠氮-炔环加成(SPAAC)反应由于具有高效快速、高选择性和生物正交性等优点被广泛用于生物医学和材料科学等多个领域。SPAAC反应不需要光、热、超声和催化剂等额外的刺激,反应的驱动力来源于高张力的活泼环状炔烃,因此合理设计环状炔烃是SPAAC反应的关键。本文详细归纳了不同环数目的环状炔烃的稳定性和反应活性,总结参与SPAAC的稳定环状炔烃,并讨论了它们参与SPAAC反应的二级反应速率常数。本文还介绍了目前应用广泛的代表性环状炔烃的制备方法研究进展。最后,对无铜催化的SPAAC的应用前景和存在的问题进行讨论和展望。

关键词： 点击化学, 环状炔烃, 叠氮-炔环加成反应, 生物正交, 环张力

In recent years, strain-promoted azide-alkyne cycloaddition (SPAAC) reaction has been widely used in many fields such as biomedicine and materials science due to its high efficiency, rapidity, high selectivity, and bioorthogonality. SPAAC reaction does not require additional stimuli such as light, heat, ultrasound or catalysts. The driving force of the reaction comes from the active cyclic alkynes with high strain. Therefore, the rational design of the cycloalkynes is the key to the SPAAC reaction. In this review, the stability and reactivity of cycloalkynes with different ring numbers are discussed, and the stable cycloalkynes participating in SPAAC smoothly as well as their second-order reaction rate constants in the SPAAC reaction are summarized. The research progress in the preparation methods of representative cyclic alkynes that are currently widely used is also introduced. Moreover, the application, challenge and future outlook of SPAAC without copper catalysis are discussed and prospected.

Key words: click chemistry, cycloalkynes, azide-alkyne cycloaddition, biorthogonality, strain
()
图式1 CuAAC反应
Scheme 1 CuAAC Reaction
图式2 SPAAC反应
Scheme 2 Strain-Promoted Azide-alkyne cycloaddition
图式3 环戊炔作为独立中间体参与加成[18]
Scheme 3 Cyclopentyne participates in the addition as an independent intermediate[18]
图式4 不稳定环己炔的脱溴/脱氢合成
Scheme 4 Debromination/dehydrogenation synthesis of unstable cyclohexyne
图1 稳定参与SPAAC反应的7元环炔烃及其开始使用的年份
Fig. 1 The 7-membered cycloalkynes that stably participate in the SPAAC reaction and the year of their use
图2 稳定参与反应的8元环炔烃及其开始使用的年份
Fig. 2 The 8-membered cycloalkynes that stably participate in the SPAAC reaction and the year of their use
图3 稳定参与反应的9元、10元环炔烃及其开始使用的年份
Fig. 3 The 9-membered and 10-membered cycloalkynes that participate in the reaction stably and the year when they were used
表1 不同环状炔烃参与SPAAC的二级反应常数
Table 1 Second order reaction constants of different cycloalkyne substrates
Cyclootyne k(×10-3 M-1·s-1)
DIFN[28] 0.059
TMBN[42] 0.20
OCT[37] 2.4
DIMAC[28] 3
MOFO[28] 4.3
PYRROC[34] 6
Sondheimer Diyne[28] 8.8
thiaDIFBO[28] 14
Tomooka[28] 19
DIFO2[40] 42
DIFO3[32] 52
DIFO[37] 76
DIBC[28] 76
TRIPCO[35] 83
SNO-OCT[28] 87
TMDIBO[32] 94
S-DIBO[40] 112
DIBO[44] 120
BCN[33] 140
DIFBO[37] 220
COMBO[36] 235
DIBONE[28] 259
DIBAC[45] 310
BARAC[38] 960
FMDIBO[41] 1010
ODIBO[28] 1660
TMTH[28] 4000
Klan[28] 22500
图式4 范德尔夫特法
Scheme 4 Van Derft method
图式5 波皮克法
Scheme 5 Popik method
图式6 溴化和消去
Scheme 6 Bromination and elimination
图式7 改良波皮克法
Scheme 7 Modified Popik Method
图4 SPAAC反应用于制备Pt的抗癌复合物[56]
Fig. 4 SPAAC reaction is used to prepare Pt anticancer complex[56]. Copyright 2020, Elsevier
图5 SPAAC反应用于制备水凝胶[85]
Fig. 5 SPAAC reaction for the preparation of hydrogels[85]. Copyright 2015, American Chemical Society
图6 SPAAC反应用于纳米平台的界面改性[96]
Fig. 6 SPAAC reaction for interfacial modification of nanoplatforms[96]. Copyright 2019, American Chemical Society
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摘要

环张力促进的叠氮-炔环加成反应