Literature DB >> 12816471

Ring-opening reactions of nonactivated aziridines catalyzed by tris(pentafluorophenyl)borane.

Iain D G Watson1, Andrei K Yudin.   

Abstract

The ring-opening reactions of nonactivated aziridines with amine nucleophiles are efficiently catalyzed by tris(pentafluorophenyl)borane leading to derivatives of trans-1,2-diamines in high yields. A mechanistic investigation of the reaction suggests that in situ formed [(C(6)F(5))(3)B(OH(2))].H(2)O catalyzes the opening through a Brønsted acid manifold.

Entities:  

Year:  2003        PMID： 12816471     DOI： 10.1021/jo0343578

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Investigation of main group promoted carbon dioxide reduction.

Authors:  Brena L Thompson; Zachariah M Heiden
Journal:  Tetrahedron       Date:  2019-02-15       Impact factor: 2.457

2.  Highly sensitive NH3 detection based on organic field-effect transistors with tris(pentafluorophenyl)borane as receptor.

Authors:  Weiguo Huang; Kalpana Besar; Rachel LeCover; Ana María Rule; Patrick N Breysse; Howard E Katz
Journal:  J Am Chem Soc       Date:  2012-09-04       Impact factor: 15.419

3.  Hydrogen bonds determine the structures of the ternary heterocyclic complexes C₂H₄O···2HF, C₂H₅N···2HF and C₂H₄S···2HF: density functional theory and topological calculations.

Authors:  Boaz G Oliveira; Regiane C M U Araújo; Antônio B Carvalho; Mozart N Ramos
Journal:  J Mol Model       Date:  2011-02-08       Impact factor: 1.810

4.  Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins Using Nonactivated N Atom Precursors.

Authors:  Tianning Deng; Wrickban Mazumdar; Yuki Yoshinaga; Pooja B Patel; Dana Malo; Tala Malo; Donald J Wink; Tom G Driver
Journal:  J Am Chem Soc       Date:  2021-11-08       Impact factor: 15.419

5.  Scope and mechanism of intramolecular aziridination of cyclopent-3-enyl-methylamines to 1-azatricyclo[2.2.1.0(2,6)]heptanes with lead tetraacetate.

Authors:  Huayou Hu; Juan A Faraldos; Robert M Coates
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

6.  Surprising Condensation Reactions of the Azadithiolate Cofactor.

Authors:  Fanjun Zhang; Casseday P Richers; Toby J Woods; Thomas B Rauchfuss
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-18       Impact factor: 16.823
  6 in total

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