Literature DB >> 19736957

Preparation of potassium azidoaryltrifluoroborates and their cross-coupling with aryl halides.

Young Ae Cho1, Dong-Su Kim, Hong Ryul Ahn, Belgin Canturk, Gary A Molander, Jungyeob Ham.   

Abstract

Potassium azidoaryltrifluoroborates have been prepared from the corresponding haloaryltrifluoroborates in 73-98% yields. Also, we successfully cross-coupled the azido-functionalized organotrifluoroborates and carried out a one-pot sequential cross-coupling/1,3-dipolar cycloaddition and a one-pot cross-coupling/azide reduction process.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19736957      PMCID： PMC2751812          DOI： 10.1021/ol901669k

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


  11 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

2.  Asymmetric 1,3-Dipolar Cycloaddition Reactions.

Authors:  Kurt V. Gothelf; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

3.  Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.

Authors:  Gary A Molander; Noel Ellis
Journal:  Acc Chem Res       Date:  2007-01-26       Impact factor: 22.384

Review 4.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

Review 5.  Cu-catalyzed azide-alkyne cycloaddition.

Authors:  Morten Meldal; Christian Wenzel Tornøe
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

6.  A facile one-pot preparation of organoselanyltrifluoroborates from dihalobenzenes and their cross-coupling reaction.

Authors:  Hong Ryul Ahn; Young Ae Cho; Dong-Su Kim; Jungwook Chin; Young-Soo Gyoung; Seokjoon Lee; Heonjoong Kang; Jungyeob Ham
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

7.  Organic azides: an exploding diversity of a unique class of compounds.

Authors:  Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

8.  Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Org Lett       Date:  2008-04-26       Impact factor: 6.005

9.  Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Org Lett       Date:  2007-03-17       Impact factor: 6.005

10.  Synthesis of aryl azides and vinyl azides via proline-promoted CuI-catalyzed coupling reactions.

Authors:  Wei Zhu; Dawei Ma
Journal:  Chem Commun (Camb)       Date:  2004-03-05       Impact factor: 6.222
View more
  5 in total

1.  Copper(II)-Catalyzed Conversion of Aryl/Heteroaryl Boronic Acids, Boronates, and Trifluoroborates into the Corresponding Azides: Substrate Scope and Limitations.

Authors:  Kimberly D Grimes; Amol Gupte; Courtney C Aldrich
Journal:  Synthesis (Stuttg)       Date:  2010-05-01       Impact factor: 3.157

2.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

3.  Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2014-05-06       Impact factor: 4.354

4.  Development of a Suzuki cross-coupling reaction between 2-azidoarylboronic pinacolate esters and vinyl triflates to enable the synthesis of [2,3]-fused indole heterocycles.

Authors:  Navendu Jana; Quyen Nguyen; Tom G Driver
Journal:  J Org Chem       Date:  2014-03-12       Impact factor: 4.354

5.  Azidophenyl as a click-transformable redox label of DNA suitable for electrochemical detection of DNA-protein interactions.

Authors:  Jana Balintová; Jan Špaček; Radek Pohl; Marie Brázdová; Luděk Havran; Miroslav Fojta; Michal Hocek
Journal:  Chem Sci       Date:  2014-09-16       Impact factor: 9.825
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.