Literature DB >> 14664574

Aerobic ruthenium-catalyzed oxidative cyanation of tertiary amines with sodium cyanide.

Shun-Ichi Murahashi1, Naruyoshi Komiya, Hiroyuki Terai, Takahiro Nakae.   

Abstract

RuCl3-catalyzed oxidative cyanation of tertiary amines with sodium cyanide under molecular oxygen (1 atm) at 60 degrees C gives the corresponding alpha-aminonitriles, which are versatile synthetic intermediates of various compounds such as amino acids and unsymmetrical 1,2-diamines, in excellent yields. This reaction is clean and should be an environmentally benign and useful process.

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Year:  2003        PMID: 14664574     DOI: 10.1021/ja0390303

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  19 in total

1.  The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

Authors:  Arthur J Catino; Jason M Nichols; Brian J Nettles; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2006-05-03       Impact factor: 15.419

2.  Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

Authors:  Zhiping Li; D Scott Bohle; Chao-Jun Li
Journal:  Proc Natl Acad Sci U S A       Date:  2006-06-05       Impact factor: 11.205

3.  Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Authors:  Anh T Tran; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-24       Impact factor: 15.336

4.  Total synthesis of lepadiformine alkaloids using N-Boc α-amino nitriles as trianion synthons.

Authors:  Matthew A Perry; Matthew D Morin; Brian W Slafer; Scott D Rychnovsky
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

5.  Condensation-Based Methods for the C-H Bond Functionalization of Amines.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2021-09-02       Impact factor: 3.157

6.  Regioselective α-Cyanation of Unprotected Alicyclic Amines.

Authors:  Fuchao Yu; Daniel A Valles; Weijie Chen; Scott D Daniel; Ion Ghiviriga; Daniel Seidel
Journal:  Org Lett       Date:  2022-08-29       Impact factor: 6.072

7.  Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Authors:  Giulia Bergonzini; Corinna S Schindler; Carl-Johan Wallentin; Eric N Jacobsen; Corey R J Stephenson
Journal:  Chem Sci       Date:  2014-01       Impact factor: 9.825

8.  Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

Review 9.  Development of biomimetic catalytic oxidation methods and non-salt methods using transition metal-based acid and base ambiphilic catalysts.

Authors:  Shun-Ichi Murahashi
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2011       Impact factor: 3.493

10.  Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolines via a mixed C-N/C-O-forming cascade.

Authors:  Quintin Elliott; Gabriel Dos Passos Gomes; Christopher J Evoniuk; Igor V Alabugin
Journal:  Chem Sci       Date:  2020-02-21       Impact factor: 9.825

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