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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
a   Euromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco
b   CEISAM Laboratory, UMR-CNRS 6230, University of Nantes, Faculty of Sciences and Technologies, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
c   Faculty of Sciences and Technologies Mohammedia, University Hassan 2, URAC 22 FSTM University Hassan II – Casablanca, BP 146, 28800 Mohammedia, Morocco
,
Nabil El Brahmi
a   Euromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco
,
Sylvain Collet
b   CEISAM 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
b   CEISAM 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
b   CEISAM 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
c   Faculty of Sciences and Technologies Mohammedia, University Hassan 2, URAC 22 FSTM University Hassan II – Casablanca, BP 146, 28800 Mohammedia, Morocco
,
Gérald Guillaumet
a   Euromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco
d   Institute of Organic and Analytical Chemistry, University of Orleans, UMR CNRS, 7311, BP 6759, 45067 Orleans Cedex 2, France
,
Jacques Lebreton
b   CEISAM 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∗
a   Euromed Research Center, Euromed Faculty of Pharmacy, Euromed University of Fes (UEMF), Route de Meknes, 30000 Fez, Morocco
› Author AffiliationsThis work was financially supported by the Euromed University of Fes, the CNRST of Rabat, and the University of Nantes (CEISAM laboratory-Symbiose group).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1891-0797.
  • Supporting Information


Publication History

Received: 28 April 2022

Accepted after revision: 04 July 2022

Accepted Manuscript online:
04 July 2022

Article published online:
01 August 2022

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