Literature DB >> 19035380

Direct zincation of functionalized aromatics and heterocycles by using a magnesium base in the presence of ZnCl2.

Zhibing Dong1, Giuliano C Clososki, Stefan H Wunderlich, Andreas Unsinn, Jinshan Li, Paul Knochel.   

Abstract

A wide range of polyfunctional aryl and heteroaryl zinc reagents were efficiently prepared in THF by using (TMP)(2)Mg2 LiCl (TMP=2,2,6,6-tetramethylpiperamidyl) in the presence of ZnCl(2). The possible pathways of this metalation procedure as well as possible reactive intermediates are discussed. This experimental protocol expands the tolerance of functional groups and allows an efficient zincation of sensitive heterocycles such as quinoxaline or pyrazine. The zincated arenes and heteroarenes react with various electrophiles providing the expected products in 60-95 % yield.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19035380     DOI： 10.1002/chem.200801558

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  8 in total

1.  Exposing the hidden complexity of stoichiometric and catalytic metathesis reactions by elucidation of Mg-Zn hybrids.

Authors:  Eva Hevia; Jonathan Z Chua; Pablo García-Alvarez; Alan R Kennedy; Matthew D McCall
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-08       Impact factor: 11.205

2.  Structural basis for regioisomerization in the alkali-metal-mediated zincation (AMMZn) of trifluoromethyl benzene by isolation of kinetic and thermodynamic intermediates.

Authors:  David R Armstrong; Victoria L Blair; William Clegg; Sophie H Dale; Joaquin Garcia-Alvarez; Gordon W Honeyman; Eva Hevia; Robert E Mulvey; Luca Russo
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

3.  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

4.  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

5.  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

6.  Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

Authors:  Alexander Kremsmair; Andreas Hess; Benjamin Heinz; Paul Knochel
Journal:  Chemistry       Date:  2021-11-29       Impact factor: 5.020

7.  Structurally defined potassium-mediated zincation of pyridine and 4-R-substituted pyridines (R = Et, iPr, tBu, Ph, and Me2N) by using dialkyl-TMP-zincate bases.

Authors:  William Clegg; Ben Conway; David V Graham; Eva Hevia; Alan R Kennedy; Robert E Mulvey; Luca Russo; Dominic S Wright
Journal:  Chemistry       Date:  2009-07-20       Impact factor: 5.236

8.  Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation.

Authors:  Marc Magre; Eva Paffenholz; Bholanath Maity; Luigi Cavallo; Magnus Rueping
Journal:  J Am Chem Soc       Date:  2020-08-04       Impact factor: 15.419
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.