Regioselective C–H Activation of Substituted Pyridines and other Azines using Mg- and Zn-TMP-Bases
Open Access
- 18 January 2018
- journal article
- review article
- Published by Georg Thieme Verlag KG in SynOpen
- Vol. 02 (01), 0078-0095
- https://doi.org/10.1055/s-0036-1591966
Abstract
The metalation of substituted pyridines, diazines and related N-heterocycles using TMPMgCl·LiCl, TMP2Mg·2LiCl, TMPZnCl·LiCl or TMP2Zn·2LiCl2·2MgCl2 (TMP = 2,2,6,6-tetramethylpiperidyl) in the presence or absence of a Lewis acid is reviewed. Contents 1 Introduction 2 Magnesiation of Pyridines and Related Azines 2.1 Magnesiations using TMPMgCl·LiCl 2.2 Magnesiations using TMP2Mg·2LiCl and Related Bases 2.3 BF3·OEt2 Promoted Metalations of Pyridines 3 Zincation of Pyridines and Related Azines using TMPZnCl·LiCl and TMP2Zn·2LiCl·2MgCl2 4 Metalation of Pyridines using other TMP-Bases 5 Magnesiation and Zincation of Diazines 6 ConclusionKeywords
Funding Information
- DeutscheForschungsGemeinschaft (SFB749)
This publication has 113 references indexed in Scilit:
- Heterocyclic chemistry in crop protectionPest Management Science, 2013
- Computed CH Acidity of Biaryl Compounds and Their Deprotonative Metalation by Using a Mixed Lithium/Zinc‐TMP BaseChemistry – A European Journal, 2013
- The orthoandmetaMagnesiation of Functionalized Anilines and Amino-Substituted Pyridines and Pyrazines at Room TemperatureAngewandte Chemie, 2012
- Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagentsBeilstein Journal of Organic Chemistry, 2011
- Selective and Multiple Functionalization of Pyridines and Alkaloids via Mg- and Zn-Organometallic IntermediatesOrganic Letters, 2011
- Difunctionalisation of Arenes and Heteroarenes by Directed Metallation and Sulfoxide–Magnesium ExchangeChemistry – A European Journal, 2011
- Iron-Catalyzed Heterocycle and Arene Deprotonative AlkylationOrganic Letters, 2010
- Atom‐Economical Preparation of Aryl– and Heteroaryl–Lanthanum Reagents by Directed ortho‐Metalation by Using tmp3[La]Chemistry – A European Journal, 2010
- Aluminum Bases for the Highly Chemoselective Preparation of Aryl and Heteroaryl Aluminum CompoundsAngewandte Chemie, 2009
- The 2×3 Toolbox of Organometallic Methods for Regiochemically Exhaustive FunctionalizationAngewandte Chemie, 2004