Literature DB >> 31034125

Lewis Acid Directed Regioselective Metalations of Pyridazine.

Moritz Balkenhohl1, Harish Jangra1, Tobias Lenz1, Marian Ebeling1, Hendrik Zipse1, Konstantin Karaghiosoff1, Paul Knochel1.   

Abstract

Mono- or bidentate boron Lewis acids trigger a regioselective magnesiation or zincation of pyridazine in position C3 (ortho product) or C4 (meta product). The regioselectivity of the metalation was rationalized with the help of calculated pKa values of both pyridazine and pyridazine/Lewis acid complexes.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  TMP bases; frustrated Lewis pairs; magnesiation; pyridazine; zincation

Year:  2019        PMID： 31034125     DOI： 10.1002/anie.201903839

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  4 in total

1.  N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines with Enamines Promoted by the Lewis Acid ZnCl2.

Authors:  Zixi Zhu; Dale L Boger
Journal:  J Org Chem       Date:  2022-04-13       Impact factor: 4.198

2.  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

3.  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

4.  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
  4 in total

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