Ab initio quantum-mechanical and experimental mechanistic studies of Diels-Alder reactions between unsubstituted and phenyl-substituted acetylenes and 1,2,4,5-tetrazines

Ciosłowski, Jerzy; Sauer, Jürgen; Hetzenegger, Josef; Karcher, T.; Hierstetter, Thomas

doi:10.1021/ja00057a019

Cited by 50 publications

(34 citation statements)

References 3 publications

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“…The De Rosa group has performed extensive research on the reactiono fa minopyrroles with 1,3,5-triazines. As many as five intermediates have been identified by 1 HNMR, 13 CNMR, 15 NNMR, and 19 FNMR spectroscopy. [6,7] On this basis, astepwise mechanism has been proposed( Figure 1).…”

Section: Stepwise Mechanism Through Azwitterionmentioning

confidence: 99%

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Png

Zeng

et al. 2017

Chemistry An Asian Journal

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Inverse-electron-demand Diels-Alder (iEDDA) reactions are an intriguing class of cycloaddition reactions that have attracted increasing attention for their application in bioorthogonal chemistry, the total synthesis of natural products, and materials science. In many cases, the application of the iEDDA reaction has been demonstrated as an innovative approach to achieve target structures. The theoretical aspects of this class of reactions are of particular interest for scientists as a means to understand the various factors, such as steric strain and electron density of the attached groups, that govern the reaction and thus to elucidate the reaction mechanism. This review aims to summarize both theoretical investigations and application-driven research work on the iEDDA reaction. First, the historical aspects and the theoretical basis of the reaction, especially recent advances in time-dependent density functional theory (TD-DFT) calculations, as well as catalysis strategies will be highlighted and discussed. Second, the applications of this novel reaction in the context of materials science, bioorthogonal chemistry, and total synthesis of natural products will be elaborated with selected recent examples. The challenges and opportunities of the iEDDA reaction will be highlighted to give more insight into its potential applications in many other research areas.

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Section: Stepwise Mechanism Through Azwitterionmentioning

confidence: 99%

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Png

Zeng

et al. 2017

Chemistry An Asian Journal

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“…A functional of the M06 family already showed good performance for the computation of barrier heights in other similar inverse electron-demand Diels-Alder reactions. [19,36,37] The influence of water as solvent was further determined with the polarizable continuum model (PCM). [38] The addition of tetrazine to norbornene derivatives 3 and 4 can proceed from the exo-or from the endo-side, respectively.…”

mentioning

confidence: 99%

Norbornenes in Inverse Electron‐Demand Diels–Alder Reactions

Vrábel

Kölle

Brunner

et al. 2013

Chemistry A European J

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“…Cycloadditions of 3-aryl-1,2,4,5-tetrazines with alkynes predominantly forms the most sterically hindered o -isomers of the corresponding pyridazines. This observation was rationalized by ab initio calculations for the [4+2] cycloaddition of phenylacetylene to 3-phenyl-1,2,4,5-tetrazine [37]. However, for silylated, germylated and stannylated alkynes, a high regioselectivity to form the m-isomer was observed (Fig.…”

Section: Iv-2 [4+2] Cycloadditionsmentioning

confidence: 78%

“…(33) was formed and reacted with another alkyne unit (34) to give arylboronate (35). It was subject, without purification, to the Suzuki-Miyaura coupling with aryl iodide (36) in aqueous toluene to afford biaryl compound (37). As a result, this four-component coupling approach to highly substituted biaryls was successfully established by combining these two operations in a sequential one-pot process.…”

Section: Iii-3 [2+2+2] Cycloadditionsmentioning

confidence: 99%

Cycloadditions, Cycloisomerizations and Related Reactions of Alkynes Bearing Group 13 or 14 Heteroelements

Gandon¹,

Aubert²,

Malacrìa

2005

COC

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Cycloaddition and cycloisomerization reactions involving alkynes grant a rapid access to arenes, cyclic dienes, and cyclopentenone derivatives. The use of alkynes substituted by group 13 or 14 heteroelements as partners for such reactions is an emerging strategy. Indeed, the specific electronic properties of these heteroelements can play a crucial role for controlling the chemo-and regioselective outcome of a given reaction. Moreover, the heteroatoms can be considered as latent functional groups and would allow for further transformations including Suzuki-Miyaura or Stille crosscouplings. Both aspects will be presented in this review.

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Ab initio quantum-mechanical and experimental mechanistic studies of Diels-Alder reactions between unsubstituted and phenyl-substituted acetylenes and 1,2,4,5-tetrazines

Cited by 50 publications

References 3 publications

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Norbornenes in Inverse Electron‐Demand Diels–Alder Reactions

Cycloadditions, Cycloisomerizations and Related Reactions of Alkynes Bearing Group 13 or 14 Heteroelements

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