Literature DB >> 18362973

Palladium and copper-catalysed arylation reactions in the presence of water, with a focus on carbon-heteroatom bond formation.

Mónica Carril1, Raul SanMartin, Esther Domínguez.   

Abstract

Palladium and copper-catalysed arylation of amines, alcohols and thiols, powerful tools for the construction of C-N, C-O and C-S bonds, are typically carried out in organic (and often toxic) solvents. Therefore the use of such a sustainable, benign solvent as water in this context has gained growing attention. This tutorial review presents the most recent advances dealing with palladium and copper-catalysed carbon-heteroatom bond formation performed in total or partial aqueous media. The particular and distinctive features of water which are apparently responsible for the acceleration and greater chemoselectivity of the aqueous protocols will also be discussed.

Year:  2008        PMID: 18362973     DOI: 10.1039/b709565c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  15 in total

1.  Base-mediated stereospecific synthesis of aryloxy and amino substituted ethyl acrylates.

Authors:  M Shahjahan Kabir; Ojas A Namjoshi; Ranjit Verma; Michael Lorenz; V V N Phani Babu Tiruveedhula; Aaron Monte; Steven H Bertz; Alan W Schwabacher; James M Cook
Journal:  J Org Chem       Date:  2011-11-28       Impact factor: 4.354

2.  Perylenequinone natural products: evolution of the total synthesis of cercosporin.

Authors:  Barbara J Morgan; Carol A Mulrooney; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

3.  Perylenequinone natural products: total syntheses of the diastereomers (+)-phleichrome and (+)-calphostin D by assembly of centrochiral and axial chiral fragments.

Authors:  Barbara J Morgan; Carol A Mulrooney; Erin M O'Brien; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

Review 4.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

5.  Design, synthesis, and investigation of protein kinase C inhibitors: total syntheses of (+)-calphostin D, (+)-phleichrome, cercosporin, and new photoactive perylenequinones.

Authors:  Barbara J Morgan; Sangeeta Dey; Steven W Johnson; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419

6.  Cross-Coupling Biarylation of Nitroaryl Chlorides Through High Speed Ball Milling.

Authors:  Solita Lam; Yvonne Puplampu-Dove; Adrienne Morris; Ayunna Epps; Ghislain Mandouma
Journal:  Int J Innov Educ Res       Date:  2015-06

7.  Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.

Authors:  Sii Hong Lau; Peng Yu; Liye Chen; Christina B Madsen-Duggan; Michael J Williams; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2020-11-12       Impact factor: 15.419

8.  Selective Radical Amination of Aldehydic C(sp2)-H Bonds with Fluoroaryl Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of N-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative Conditions.

Authors:  Li-Mei Jin; Hongjian Lu; Yuan Cui; Christopher L Lizardi; Thiago N Arzua; Lukasz Wojtas; Xin Cui; X Peter Zhang
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

9.  On the role of metal contaminants in catalyses with FeCl3.

Authors:  Stephen L Buchwald; Carsten Bolm
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  First application of an efficient and versatile ligand for copper-catalyzed cross-coupling reactions of vinyl halides with N-heterocycles and phenols.

Authors:  M Shahjahan Kabir; Michael Lorenz; Ojas A Namjoshi; James M Cook
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

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