Reactions of fluoroalkanesulfonyl azides with vinyl ether and tetrakis(dimethylamino)ethylene

Zhu, Shizheng; He, Ping; Zhao, Jingwei; Chen, Xian

doi:10.1016/j.jfluchem.2003.11.016

Cited by 20 publications

(12 citation statements)

References 11 publications

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“…Similarly, cyclic vinyl ethers gave tetrahydropyran‐ and tetrahydrofuran‐2‐imines 86b. In the case of simple vinyl ethers the primary triazolines could be isolated 86c. Yamamoto used Nf‐protected amines for the asymmetric hydroamination of alkynes.…”

Section: Miscellaneous Reactions Including Other Perfluorosulfonylamentioning

confidence: 99%

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

2009

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How much fluoride is good for a strong electron-withdrawing effect? In this review we summarize recent results on the use of perfluoroalkanesulfonates, in particular of the cost effective nonafluorobutanesulfonates (nonaflates), in transition metal-catalyzed reactions and a few other typical transformations. During the last decade many advantages over the commonly used triflates have been discovered. The generation of alkenyl and (het)aryl nonaflates and their applications in metal-catalyzed processes such as Heck, Suzuki, Sonogashira, Stille, and Negishi couplings or amination reactions are described. Although far from a systematic investigation, all the presented results clearly demonstrate the many advantages of nonaflates and of similar higher fluorinated sulfonates in laboratory and industrial scale organic synthesis.

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Section: Miscellaneous Reactions Including Other Perfluorosulfonylamentioning

confidence: 99%

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

2009

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“…[87,88] The emergence of symmetrically substituted N,NЈ-disulfonyl-2,5-dimethoxypiperazines as side products in reactions between enol ethers and sulfonyl azides as a result of dimerisation seems to be a clear indication of the ring-opening of the cycloaddition product in an analogous manner. [87,89] On the other hand, ab initio calculations indicate that benzyl diazonium cations do not exist in the classical sense, but rather as electrostatically bound complexes between benzyl cation and dinitrogen. [90] As a consequence, betaine 47 might not exist in the precise form displayed in Scheme 2, but rather as a carbenium cation more or less loosely bound to a dinitrogen molecule.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

Direct Asymmetric α‐Sulfamidation of α‐Branched Aldehydes: A Novel Approach to Enamine Catalysis

Vogt¹,

Baumann²,

Nieger³

et al. 2006

Eur J Org Chem

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Proline‐catalysed reactions between α‐branched aldehydes and sulfonyl azides provide scalemic configurationally stabilised α‐sulfamidated products with ee values of up to 86 %. The reactions can also be carried out in a one‐pot fashion, with catalyst, aldehyde, sulfonyl chloride and sodium azide. The proposed mechanism differs fundamentally from the mechanistic model usually ascribed to enamine catalysis, containing as a key step the diastereoselective cycloaddition of the azide to an enamine formed in situ. The products obtained in the reaction can be converted into the corresponding unnatural amino acids in two additional steps.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…Generally speaking, there are two types of mechanism for the reactions of azide compounds, which are nitrene intermediate and dipolar cycloaddition process. To the best of our knowledge, the former proceeded at high temperature (usually above 110 8C for fluoroalkanesulfonyl azides 1) and the latter occurred at lower temperature [4]. Thus, the reaction pathway for these reactions is proposed as shown in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Reactions of fluoroalkanesulfonyl azides with pyrrole and its derivatives

Xiong

Xin

Han

et al. 2010

Journal of Fluorine Chemistry

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Reactions of fluoroalkanesulfonyl azides with vinyl ether and tetrakis(dimethylamino)ethylene

Cited by 20 publications

References 11 publications

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

Nine Times Fluoride can be Good for your Syntheses. Not just Cheaper: Nonafluorobutanesulfonates as Intermediates for Transition Metal‐Catalyzed Reactions

Direct Asymmetric α‐Sulfamidation of α‐Branched Aldehydes: A Novel Approach to Enamine Catalysis

Reactions of fluoroalkanesulfonyl azides with pyrrole and its derivatives

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