Topochemical Azide–Alkyne Cycloaddition Reaction,Accounts of Chemical Research

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Topochemical Azide–Alkyne Cycloaddition Reaction
Accounts of Chemical Research ( IF 16.4 ) Pub Date : 2019-10-10 , DOI: 10.1021/acs.accounts.9b00398
Kuntrapakam Hema ₁ , Kana M. Sureshan ₁

Affiliation

Topochemical reactions are solid-state reactions that transpire under the strict control of molecular packing in the crystal lattice. Due to this lattice control, these reactions generate products in a regio-/stereospecific manner and in very high yields. In a broader sense, topochemical reactions mimic nature’s way of carrying out reactions in a confined environment of enzymes giving specific products. Apart from their remarkable specificity, topochemical reactions have many other interesting features that make these reactions more attractive than solution-phase reactions. Solution-phase reactions necessitate the use of reactants, reagents, catalysts, and solvents and often give products along with varying amounts of byproducts, necessitating complex workup and chromatographic purification using various chemicals. These inevitable chemical wastes from solution-state reactions could be avoided by topochemical reactions, as they are solvent-free and catalyst-free and often do not require any chromatographic purification in view of their specificity and high yielding nature. Also the confinement offered by the crystal lattice gives products that are not possible by solution-phase reactions. Another interesting feature of topochemical reactions is the possibility of formation of products in an ordered (crystalline) form, which imparts interesting properties. Thus, topochemical reactions have control not only at the molecular level (regio-/stereospecificity) but also at the supramolecular level (packing). Many topochemical reactions happen in single-crystal-to-single-crystal (SCSC) fashion, and crystal structure analysis of such reactions often gives mechanistic insights and knowledge about the geometrical criteria required for the reaction. Despite all these attractive features, reactions that can be done topochemically are limited. There is tremendous interest in the development of new categories of topochemical reactions and strategies to achieve reactivity in crystals.

中文翻译：

拓扑化学叠氮化物-炔环加成反应

拓扑化学反应是在严格控制晶格中分子堆积的过程中发生的固态反应。由于这种晶格控制，这些反应以区域/立体特异性的方式并以非常高的产率产生产物。从广义上讲，拓扑化学反应模仿了自然界中在有限的酶产生特定产物的环境中进行反应的方式。拓扑化学反应除具有卓越的特异性外，还具有许多其他有趣的功能，这些特征使这些反应比溶液相反应更具吸引力。溶液相反应需要使用反应物，试剂，催化剂和溶剂，并且经常产生产物以及各种量的副产物，从而需要使用各种化学物质进行复杂的后处理和色谱纯化。通过溶液化学反应可以避免这些来自溶液态反应的不可避免的化学废物，因为它们是无溶剂和无催化剂的，并且鉴于其特异性和高产率的性质，通常不需要任何色谱纯化。晶格提供的限制也产生了固相反应不可能产生的产物。拓扑化学反应的另一个有趣特征是有可能形成有序（结晶）形式的产品，从而赋予了有趣的特性。因此，拓扑化学反应不仅可以控制分子水平（区域/立体特异性），而且还可以控制超分子水平（堆积）。许多拓扑化学反应以单晶到单晶（SCSC）的方式发生，此类反应的晶体结构分析通常会提供有关该反应所需几何标准的机械见解和知识。尽管具有所有这些吸引人的特征，但是可以在拓扑化学上进行的反应是有限的。人们对新的拓扑化学反应和实现晶体反应性的策略的发展抱有极大的兴趣。

更新日期：2019-10-10

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