Structure regulation and catalytic performance of amine-functionalized zeolitic imidazolate frameworks for CO2 cycloaddition
Meng LinghuYang JiakunHuo ZichenQin WuYaoyuan ZhangDaxin ShiChen KangchengHelei LiuXu XiyanHansheng LiHang Xu
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Keywords:
Zeolitic imidazolate framework
Synergistic catalysis
Enone
Sulfonyl
Intramolecular reaction
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Epichlorohydrin
Synergistic catalysis
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The enantioselective N-heterocyclic carbene-catalysed formal 2+2- and 2+2+2- cycloadditions of ketenes with isothiocyanates can be investigated. At room temperature, the reaction of N-arylthiocyanates favours the 2+2-cycloaddition. However, at −40°C, N-benzoylisothiocyanates undergo the 2+2+2-cycloaddition. This chapter discusses cycloaddition-type addition reactions. Specifically, it covers three types of cycloadditions: 2+2-cycloaddition, 2+3-cycloaddition and 2+4-cycloaddition. Miscellaneous cycloaddition reactions are separately described at the end of the chapter.
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The results of studies in intramolecular [4 + 2] cycloaddition carried out in recent years are surveyed. The synthetic possibilities of this reaction for the preparation of natural products and its high stereoselectivity and regioselectivity are demonstrated. The differences and similarities between intramolecular and intermolecular [4 + 2] cycloaddition reactions are elucidated. The bibliography includes 207 references.
Intramolecular reaction
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The [4 + 2] cycloaddition reactions of N-sulfinylphosphoramidates, prepared from the corresponding phosphoramidates by treatment with N-(chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10) and presence (>95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.
Reactivity
Lewis acid catalysis
Imidazole
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Propylene oxide
Zeolitic imidazolate framework
Imidazolate
Synergistic catalysis
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Abstract Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition. 1 Introduction 2 Formation of Carbocycles 2.1 Intermolecular Reactions 2.1.1 Cyclotrimerization of Alkynes 2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes 2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides 2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions 2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition 2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition 2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition 2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition 2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition 2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions 3 Formation of Heterocycles 3.1 Cycloaddition of Alkynes with Nitriles 3.2 Cycloaddition of 1,6-Diynes with Cyanamides 3.3 Cycloaddition of 1,6-Diynes with Selenocyanates 3.4 Cycloaddition of Imines with Allenes or Alkenes 3.5 Cycloaddition of (Thio)Cyanates and Isocyanates 3.6 Cycloaddition of 1,3,5-Triazines with Allenes 3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes 3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions 4 Conclusion
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Abstract Acetylene and ethylene are the smallest molecules that contain an unsaturated carbon–carbon bond and can be efficiently utilized in a large variety of cycloaddition reactions. In this review, we summarize the application of these C2 molecular units in cycloaddition chemistry and highlight their amazing synthetic opportunities. 1 Introduction 2 Fundamental Features and Differences of Cycloaddition Reactions Involving Acetylene and Ethylene 3 (2+1) Cycloaddition 4 [2+2] Cycloaddition 5 (3+2) Cycloaddition 6 [4+2] Cycloaddition 7 (2+2+1) Cycloaddition 8 [2+2+2] Cycloaddition 9 The Use of Acetylene and Ethylene Cycloaddition for Deuterium and 13C Labeling 10 Conclusions
Acetylene
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Abstract The photo- induced intramolecular meta-cycloaddition of bichromophore 1 gave diastereoselectively two adducts 2 and 3. The observed stereochemistry of cycloaddition is rationalized in terms of hydrogen bond effect induced by the 3-hydroxy group in the 5-phenylpent-1-ene skeleton.
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This Chapter Contains Sections titled: 2 + 2-Cycloaddition 2 + 3-Cycloaddition 2 + 4-Cycloaddition Miscellaneous Cycloadditions References A review of advances in Nickel-catalysed cycloaddition reactions directed towards the synthesis of carbocycles and heterocycles has been presented. The discussion includes the development and mechanistic studies of the Ni/NHC catalysts that couple diynes and nitriles to form pyridines. The use of vinyl cyclopropanes, aldehydes, ketones, tropones, 3-azetidinones, and 3-oxetenones as substrates in new Ni-catalysed cycloaddition reactions is also discussed. A second extensive review concerning Ni-catalysed cycloaddition reactions that have been studied since 2004 has been published. 1,3-Dipolar cycloadditions, Diels-Alder cycloadditions, 2+2+2- cycloadditions, and 3+3-cycloadditions are discussed. NHC-stabilized silylene monohydride reacted with diphenylacetylene to yield a 2,3,4,5-tetraphenyl-1-(tri-t-butylsilyl)-1H-silole via a 2+2+1-cycloaddition. DFT calculations indicate that the reaction mechanism did not include a silirene, the typical 2+1-cycloaddition product. The Rhodium-catalysed enantioselective 2+2+2-cycloaddition of silicon-containing prochiral triynes and internal alkynes yielded silicon-stereogenic dibenzosiloles with high enantoselectivities and high yields.
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Diphenylacetylene
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