“On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole
The C3 direct arylation of 1<i>H</i>-indazole and 1<i>H</i>-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1<i>H</i>-indazol...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/12/2820 |
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| author | Khadija Gambouz Abdelmoula El Abbouchi Sarah Nassiri Franck Suzenet Mostapha Bousmina Mohamed Akssira Gérald Guillaumet Saïd El Kazzouli |
| author_facet | Khadija Gambouz Abdelmoula El Abbouchi Sarah Nassiri Franck Suzenet Mostapha Bousmina Mohamed Akssira Gérald Guillaumet Saïd El Kazzouli |
| author_sort | Khadija Gambouz |
| collection | DOAJ |
| description | The C3 direct arylation of 1<i>H</i>-indazole and 1<i>H</i>-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1<i>H</i>-indazoles and C3-aryled 1<i>H</i>-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh<sub>3</sub> was effective as a ligand along with a lower charge of the catalyst Pd(OAc)<sub>2</sub> (5 mol%) at 100 °C, leading to C3-aryled 1<i>H</i>-indazoles or C3-aryled 1<i>H</i>-7-azaindazoles in moderate to good yields. |
| first_indexed | 2024-03-10T19:03:12Z |
| format | Article |
| id | doaj.art-6aad5dbc50664a88be96b462eec6b0fd |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:03:12Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6aad5dbc50664a88be96b462eec6b0fd2023-11-20T04:16:14ZengMDPI AGMolecules1420-30492020-06-012512282010.3390/molecules25122820“On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-AzaindazoleKhadija Gambouz0Abdelmoula El Abbouchi1Sarah Nassiri2Franck Suzenet3Mostapha Bousmina4Mohamed Akssira5Gérald Guillaumet6Saïd El Kazzouli7Faculty of Sciences and Technologies Mohammedia, University Hassan 2, URAC 22 FSTM University Hassan II—Casablanca, BP 146, Mohammedia 28800, MoroccoInstitut de Chimie Organique et Analytique, University of Orléans, UMR CNRS 7311, BP 6759, CEDEX 2, 54067 Orléans, FranceInstitut de Chimie Organique et Analytique, University of Orléans, UMR CNRS 7311, BP 6759, CEDEX 2, 54067 Orléans, FranceInstitut de Chimie Organique et Analytique, University of Orléans, UMR CNRS 7311, BP 6759, CEDEX 2, 54067 Orléans, FranceEuromed Research Center, Euromed Institute of Technology, Euromed University of Fes (UEMF), Route de Meknès, Rond-point de Bensouda, Fes 30000, MoroccoFaculty of Sciences and Technologies Mohammedia, University Hassan 2, URAC 22 FSTM University Hassan II—Casablanca, BP 146, Mohammedia 28800, MoroccoInstitut de Chimie Organique et Analytique, University of Orléans, UMR CNRS 7311, BP 6759, CEDEX 2, 54067 Orléans, FranceEuromed Research Center, Euromed Institute of Technology, Euromed University of Fes (UEMF), Route de Meknès, Rond-point de Bensouda, Fes 30000, MoroccoThe C3 direct arylation of 1<i>H</i>-indazole and 1<i>H</i>-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1<i>H</i>-indazoles and C3-aryled 1<i>H</i>-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh<sub>3</sub> was effective as a ligand along with a lower charge of the catalyst Pd(OAc)<sub>2</sub> (5 mol%) at 100 °C, leading to C3-aryled 1<i>H</i>-indazoles or C3-aryled 1<i>H</i>-7-azaindazoles in moderate to good yields.https://www.mdpi.com/1420-3049/25/12/2820indazoleazaindazolearylationgreen chemistryC–H functionalizationwater |
| spellingShingle | Khadija Gambouz Abdelmoula El Abbouchi Sarah Nassiri Franck Suzenet Mostapha Bousmina Mohamed Akssira Gérald Guillaumet Saïd El Kazzouli “On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole Molecules indazole azaindazole arylation green chemistry C–H functionalization water |
| title | “On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole |
| title_full | “On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole |
| title_fullStr | “On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole |
| title_full_unstemmed | “On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole |
| title_short | “On Water” Palladium Catalyzed Direct Arylation of 1<i>H</i>-Indazole and 1<i>H</i>-7-Azaindazole |
| title_sort | on water palladium catalyzed direct arylation of 1 i h i indazole and 1 i h i 7 azaindazole |
| topic | indazole azaindazole arylation green chemistry C–H functionalization water |
| url | https://www.mdpi.com/1420-3049/25/12/2820 |
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