Literature DB >> 23421375

New preparation of TMPZnCl·LiCl by Zn insertion into TMPCl. Application to the functionalization of dibromodiazines.

Andreas Unsinn1, Mark J Ford, Paul Knochel.   

Abstract

A practical zinc insertion starting from cheap commercial zinc powder and TMPCl (1-chloro-2,2,6,6-tetramethylpiperidine) allows a fast and efficient synthesis of the zinc base TMPZnCl·LiCl under mild conditions in high yields. This base is kinetically highly active and was used for the regio- and chemoselective functionalization of dibromodiazines (pyridazines and pyrazines).

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Year:  2013        PMID： 23421375     DOI： 10.1021/ol400248e

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


  6 in total

1.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

2.  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

3.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336

4.  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

5.  Reliable Functionalization of 5,6-Fused Bicyclic N-Heterocycles Pyrazolopyrimidines and Imidazopyridazines via Zinc and Magnesium Organometallics.

Authors:  Saroj Kumar Rout; Agonist Kastrati; Harish Jangra; Kuno Schwärzer; Alisa S Sunagatullina; Maximilien Garny; Fabio Lima; Cara E Brocklehurst; Konstantin Karaghiosoff; Hendrik Zipse; Paul Knochel
Journal:  Chemistry       Date:  2022-05-11       Impact factor: 5.020

6.  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
  6 in total

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