Solvent/Ligand-Controlled Switchable C3 or C7 C–H Arylations of 1-Methyl-4-nitro-1H-indazole

Khalid Boujdi; Nabil El Brahmi; Sylvain Collet; Didier Dubreuil; Monique Mathé-Allainmat; Mohamed Akssira; Gérald Guillaumet; Jacques Lebreton; Saïd El Kazzouli

doi:10.1055/a-1891-0797

Synthesis, Table of Contents

Synthesis 2022; 54(21): 4834-4842
DOI: 10.1055/a-1891-0797

paper

Solvent/Ligand-Controlled Switchable C3 or C7 C–H Arylations of 1-Methyl-4-nitro-1H-indazole

Khalid Boujdi

^aEuromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco

^bCEISAM Laboratory, UMR-CNRS 6230, University of Nantes, Faculty of Sciences and Technologies, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France

^cFaculty of Sciences and Technologies Mohammedia, University Hassan 2, URAC 22 FSTM University Hassan II – Casablanca, BP 146, 28800 Mohammedia, Morocco

,

Nabil El Brahmi

^aEuromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco

,

Sylvain Collet

^bCEISAM Laboratory, UMR-CNRS 6230, University of Nantes, Faculty of Sciences and Technologies, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France

,

Didier Dubreuil

^bCEISAM Laboratory, UMR-CNRS 6230, University of Nantes, Faculty of Sciences and Technologies, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France

,

Monique Mathé-Allainmat

^bCEISAM Laboratory, UMR-CNRS 6230, University of Nantes, Faculty of Sciences and Technologies, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France

,

Mohamed Akssira

^cFaculty of Sciences and Technologies Mohammedia, University Hassan 2, URAC 22 FSTM University Hassan II – Casablanca, BP 146, 28800 Mohammedia, Morocco

,

Gérald Guillaumet

^aEuromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco

^dInstitute of Organic and Analytical Chemistry, University of Orleans, UMR CNRS, 7311, BP 6759, 45067 Orleans Cedex 2, France

,

Jacques Lebreton

^bCEISAM Laboratory, UMR-CNRS 6230, University of Nantes, Faculty of Sciences and Technologies, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France

,

Saïd El Kazzouli∗

^aEuromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco

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Abstract

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Abstract

A new solvent/ligand-controlled switchable C–H arylation of 1-methyl-4-nitro-1H-indazole catalyzed by Pd(OAc)₂ was achieved. A bidentate ligand in DMA promoted the activation at C7 position, while a phosphine ligand in H₂O oriented the arylation at C3 position. The C3 and C7 arylation products were obtained in moderate to good yields and with high regioselectivity.

Key words

heteroarenes - indazole - C–H activation - C–H arylation - regioselectivity

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References

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