Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings
In recent years, there has been growing interest in the development of greener alternatives to traditional reagents used in carbon–carbon coupling reactions, particularly in response to environmental concerns. The commonly used aryl halides, despite being highly reactive in the Suzuki–Miyaura coupli...
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| Format: | Article |
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MDPI AG
2024-12-01
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| Series: | Molecules |
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| author | Jules Perney Alexandre Humblot-Negri Carlos Vaca-Garcia Sébastien Lemouzy Martine Urrutigoïty |
| author_facet | Jules Perney Alexandre Humblot-Negri Carlos Vaca-Garcia Sébastien Lemouzy Martine Urrutigoïty |
| author_sort | Jules Perney |
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| description | In recent years, there has been growing interest in the development of greener alternatives to traditional reagents used in carbon–carbon coupling reactions, particularly in response to environmental concerns. The commonly used aryl halides, despite being highly reactive in the Suzuki–Miyaura coupling (SMC), pose significant environmental risks. As a result, research has shifted towards exploring the use of phenols, which are widely accessible and environmentally benign. However, phenols are considerably less reactive due to the poor leaving group properties of the hydroxyl group, necessitating prior activation to facilitate their use in coupling reactions. This work aims to review the recent investigations on the activation strategies for phenols, focusing on their application in the Suzuki–Miyaura and related C-C couplings. In addition, the exploration of the potential of conducting the activation step “in situ” will also be discussed. We hope that this article will pave the way for the development of more sustainable and efficient coupling methodologies, addressing both ecological and practical challenges in organic synthesis. |
| format | Article |
| id | doaj-art-de657312bde4475cac1e6cdd41d955cb |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-de657312bde4475cac1e6cdd41d955cb2025-01-10T13:18:43ZengMDPI AGMolecules1420-30492024-12-013015110.3390/molecules30010051Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C CouplingsJules Perney0Alexandre Humblot-Negri1Carlos Vaca-Garcia2Sébastien Lemouzy3Martine Urrutigoïty4Laboratoire de Chimie Agro-Industrielle, INRAE, Toulouse-INP, Université de Toulouse, 31030 Toulouse, FranceLaboratoire de Chimie Agro-Industrielle, INRAE, Toulouse-INP, Université de Toulouse, 31030 Toulouse, FranceLaboratoire de Chimie Agro-Industrielle, INRAE, Toulouse-INP, Université de Toulouse, 31030 Toulouse, FranceLaboratoire de Chimie Agro-Industrielle, INRAE, Toulouse-INP, Université de Toulouse, 31030 Toulouse, FranceLaboratoire de Chimie de Coordination, CNRS, Toulouse-INP, Université de Toulouse, 31000 Toulouse, FranceIn recent years, there has been growing interest in the development of greener alternatives to traditional reagents used in carbon–carbon coupling reactions, particularly in response to environmental concerns. The commonly used aryl halides, despite being highly reactive in the Suzuki–Miyaura coupling (SMC), pose significant environmental risks. As a result, research has shifted towards exploring the use of phenols, which are widely accessible and environmentally benign. However, phenols are considerably less reactive due to the poor leaving group properties of the hydroxyl group, necessitating prior activation to facilitate their use in coupling reactions. This work aims to review the recent investigations on the activation strategies for phenols, focusing on their application in the Suzuki–Miyaura and related C-C couplings. In addition, the exploration of the potential of conducting the activation step “in situ” will also be discussed. We hope that this article will pave the way for the development of more sustainable and efficient coupling methodologies, addressing both ecological and practical challenges in organic synthesis.https://www.mdpi.com/1420-3049/30/1/51Suzuki–Miyaura couplingcross couplingphenol derivativeshomogeneous catalysisgreen chemistry |
| spellingShingle | Jules Perney Alexandre Humblot-Negri Carlos Vaca-Garcia Sébastien Lemouzy Martine Urrutigoïty Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings Molecules Suzuki–Miyaura coupling cross coupling phenol derivatives homogeneous catalysis green chemistry |
| title | Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings |
| title_full | Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings |
| title_fullStr | Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings |
| title_full_unstemmed | Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings |
| title_short | Weakly-Activated Phenol Derivatives as New Green Electrophilic Partners in Suzuki–Miyaura and Related C-C Couplings |
| title_sort | weakly activated phenol derivatives as new green electrophilic partners in suzuki miyaura and related c c couplings |
| topic | Suzuki–Miyaura coupling cross coupling phenol derivatives homogeneous catalysis green chemistry |
| url | https://www.mdpi.com/1420-3049/30/1/51 |
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