Literature DB >> 19317432

TMPZnCl.LiCl: a new active selective base for the directed zincation of sensitive aromatics and heteroaromatics.

Marc Mosrin1, Paul Knochel.   

Abstract

A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF via direct zincation using TMPZnCl.LiCl, a new exceptionally mild and efficient base. Activated arenes and heteroarenes are metalated at room temperature. Remarkably, sensitive functions such as an aldehyde as well as a nitro group are tolerated, expanding significantly the scope of directed metalations.

Entities:  

Year:  2009        PMID： 19317432     DOI： 10.1021/ol900342a

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


  13 in total

1.  Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization.

Authors:  Thanh Truong; Joseph Alvarado; Ly Dieu Tran; Olafs Daugulis
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Copper-Catalyzed Electrophilic Amination of Heteroaromatic and Aromatic C-H Bonds via TMPZnCl•LiCl Mediated Metalation.

Authors:  Stacey L McDonald; Charles E Hendrick; Katie J Bitting; Qiu Wang
Journal:  Organic Synth       Date:  2015-11-17

3.  An aromatic Glaser-Hay reaction.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

4.  Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

Authors:  Stacey L McDonald; Charles E Hendrick; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-25       Impact factor: 15.336

5.  Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation.

Authors:  David R Armstrong; Liam Balloch; Eva Hevia; Alan R Kennedy; Robert E Mulvey; Charles T O'Hara; Stuart D Robertson
Journal:  Beilstein J Org Chem       Date:  2011-09-06       Impact factor: 2.883

6.  Synergic transformation of an ethylenediamine to a lithium 1,3-diaza-2-zincacyclopentene via an alkyllithium/bis(alkyl)zinc mixture.

Authors:  Ross Campbell; Pablo García-Alvarez; Alan R Kennedy; Robert E Mulvey
Journal:  Chemistry       Date:  2010-09-03       Impact factor: 5.236

7.  Selective Functionalization of Tetrathiafulvalene Using Mg- and Zn-TMP-Bases: Preparation of Mono-, Di-, Tri-, and Tetrasubstituted Derivatives.

Authors:  Julia Nafe; Florian Auras; Konstantin Karaghiosoff; Thomas Bein; Paul Knochel
Journal:  Org Lett       Date:  2015-10-15       Impact factor: 6.005

8.  Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans-Metal-Trapping.

Authors:  Marina Uzelac; Alan R Kennedy; Eva Hevia; Robert E Mulvey
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

9.  Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki-Miyaura Cross Coupling with Electron-Poor Substrates.

Authors:  David Bulfield; Stefan M Huber
Journal:  J Org Chem       Date:  2017-12-04       Impact factor: 4.354

10.  A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl⋅LiCl.

Authors:  Moritz Balkenhohl; Harish Jangra; Ilya S Makarov; Shu-Mei Yang; Hendrik Zipse; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 16.823
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