Literature DB >> 16956219

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

Zhihui Zhang1, Lanny S Liebeskind.   

Abstract

A new method for the synthesis of nitriles is described. As a complement to the classic cyanation of aryl halides using cyanide sources and a transition metal catalyst, the palladium-catalyzed cross-coupling of thiocyanates with boronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) affords nitriles in good to excellent yields.

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Year:  2006        PMID： 16956219      PMCID： PMC2561219          DOI： 10.1021/ol061741t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

1.  Switchable catalysis: modular synthesis of functionalized Pyrimidinones via selective sulfide and halide cross-coupling chemistry.

Authors:  Carrie Kusturin; Lanny S Liebeskind; Hayat Rahman; Kirby Sample; Barbara Schweitzer; Jiri Srogl; William L Neumann
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005

2.  Nonbasic, room temperature, palladium-catalyzed coupling of aryl and alkenyl iodides with boronic acids mediated by copper(I) thiophene-2-carboxylate (CuTC).

Authors:  C Savarin; L S Liebeskind
Journal:  Org Lett       Date:  2001-07-12       Impact factor: 6.005

3.  The preparation of nitriles.

Authors:  D T MOWRY
Journal:  Chem Rev       Date:  1948-04       Impact factor: 60.622

4.  Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling.

Authors:  C Savarin; J Srogl; L S Liebeskind
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

5.  Enantioselective total synthesis of litseaverticillols A and B.

Authors:  Akira Morita; Shigefumi Kuwahara
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

6.  Ligand-free palladium-catalyzed cyanation of aryl halides.

Authors:  Steven A Weissman; Daniel Zewge; Cheng Chen
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

7.  A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines.

Authors:  Carrie L Kusturin; Lanny S Liebeskind; William L Neumann
Journal:  Org Lett       Date:  2002-03-21       Impact factor: 6.005

8.  Copper-catalyzed domino halide exchange-cyanation of aryl bromides.

Authors:  Jacopo Zanon; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2003-03-12       Impact factor: 15.419

9.  Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether.

Authors:  France-Aimée Alphonse; Franck Suzenet; Anne Keromnes; Bruno Lebret; Gérald Guillaumet
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005

10.  Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air.

Authors:  Olga Grossman; Dmitri Gelman
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005
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  6 in total

1.  Transition Metals Catalyzed Element-Cyano Bonds Activations.

Authors:  Rui Wang; John R Falck
Journal:  Catal Rev Sci Eng       Date:  2014-07       Impact factor: 20.217

2.  A new paradigm for carbon-carbon bond formation: aerobic, copper-templated cross-coupling.

Authors:  Janette M Villalobos; Jiri Srogl; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2007-11-30       Impact factor: 15.419

3.  E- and Z-, di- and tri-substituted alkenyl nitriles through catalytic cross-metathesis.

Authors:  Yucheng Mu; Thach T Nguyen; Ming Joo Koh; Richard R Schrock; Amir H Hoveyda
Journal:  Nat Chem       Date:  2019-04-01       Impact factor: 24.427

4.  Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions.

Authors:  Qing Huang; Xiangjun Peng; Hong Li; Haiping He; Liangxian Liu
Journal:  Molecules       Date:  2022-01-25       Impact factor: 4.411

5.  Ag/Pyridine Co-Mediated Oxidative Arylthiocyanation of Activated Alkenes.

Authors:  De-Long Kong; Jian-Xun Du; Wei-Ming Chu; Chun-Ying Ma; Jia-Yi Tao; Wen-Hua Feng
Journal:  Molecules       Date:  2018-10-22       Impact factor: 4.411

6.  Pd-Catalyzed Directed Thiocyanation Reaction by C-H Bond Activation.

Authors:  Mélissa Gao; Mu-Yi Chen; Xavier Pannecoucke; Philippe Jubault; Tatiana Besset
Journal:  Chemistry       Date:  2020-11-03       Impact factor: 5.236
  6 in total

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