CC BY-ND-NC 4.0 · SynOpen 2018; 02(01): 0078-0095
DOI: 10.1055/s-0036-1591966
review
Copyright with the author

Regioselective C–H Activation of Substituted Pyridines and other Azines using Mg- and Zn-TMP-Bases

Moritz Balkenhohl
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377 München, Germany   Email: Paul.Knochel@cup.uni-muenchen.de
,
Department of Chemistry, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377 München, Germany   Email: Paul.Knochel@cup.uni-muenchen.de
› Author Affiliations
We would like to thank the DFG (SFB749) for financial support
Further Information

Publication History

Received: 31 January 2018

Accepted: 04 March 2018

Publication Date:
19 March 2018 (online)

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 Conclusion

 
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