Literature DB >> 15704998

Ligand-free palladium-catalyzed cyanation of aryl halides.

Steven A Weissman1, Daniel Zewge, Cheng Chen.   

Abstract

[reaction: see text] A practical, ligand-free cyanation of aryl bromides that utilizes as little as 0.1 mol % Pd(OAc)(2) in combination with a nontoxic cyanide source, M(4)[Fe(CN)(6)] (M = K, Na), is described. The reactions are performed in DMAC at 120 degrees C and provide the corresponding aryl nitrile in 83-96% yield, typically in less than 5 h. TON values of up to 7100 were attained.

Entities:  

Year:  2005        PMID： 15704998     DOI： 10.1021/jo0481250

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


  6 in total

1.  Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids.

Authors:  Zhihui Zhang; Lanny S Liebeskind
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

2.  A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides.

Authors:  Todd D Senecal; Wei Shu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-09       Impact factor: 15.336

3.  Design and synthesis of dual 5-HT1A and 5-HT7 receptor ligands.

Authors:  Edward Ofori; Xue Y Zhu; Jagan R Etukala; Kwakye Peprah; Kamanski R Jordan; Adia A Adkins; Barbara A Bricker; Hye J Kang; Xi-Ping Huang; Bryan L Roth; Seth Y Ablordeppey
Journal:  Bioorg Med Chem       Date:  2016-05-27       Impact factor: 3.641

4.  Ex situ generation of stoichiometric HCN and its application in the Pd-catalysed cyanation of aryl bromides: evidence for a transmetallation step between two oxidative addition Pd-complexes.

Authors:  Steffan K Kristensen; Espen Z Eikeland; Esben Taarning; Anders T Lindhardt; Troels Skrydstrup
Journal:  Chem Sci       Date:  2017-10-06       Impact factor: 9.825

Review 5.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858

6.  Sea-Island-Like Morphology of CuNi Bimetallic Nanoparticles Uniformly Anchored on Single Layer Graphene Oxide as a Highly Efficient and Noble-Metal-Free Catalyst for Cyanation of Aryl Halides.

Authors:  Gopiraman Mayakrishnan; Vijayakumar Elayappan; Ick Soo Kim; Ill-Min Chung
Journal:  Sci Rep       Date:  2020-01-20       Impact factor: 4.379
  6 in total

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