Pd-Catalyzed and ligand-enabled alkene difunctionalization unactivated C-H bond functionalization
Palladium-catalyzed and ligand-enabled C-H functionalization methods have emerged as a powerful approach for the preparation of therapeutically important motifs and complex natural products. Olefins, owing to their natural abundance, have been extensively employed for the formation of C-C and C-X bo...
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| Published in | Chemical communications (Cambridge, England) Vol. 57; no. 91; pp. 1245 - 1257 |
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| Main Authors | , , |
| Format | Journal Article |
| Published |
16.11.2021
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| Online Access | Get full text |
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| Abstract | Palladium-catalyzed and ligand-enabled C-H functionalization methods have emerged as a powerful approach for the preparation of therapeutically important motifs and complex natural products. Olefins, owing to their natural abundance, have been extensively employed for the formation of C-C and C-X bonds and the generation of various heterocycles. Traditionally, activated as well as starting materials with preinstalled functional groups, and also halide substrates under transition metal catalysis, have been employed for olefin difunctionalization. However, strategies for employing unactivated C-H bond functionalization to achieve alkene difunctionalization have rarely been explored. A possible solution to this challenge is the application of bulky ligands which enhances the reductive elimination pathway and inhibits β-hydride elimination to selectively yield difunctionalized alkene products. This feature article summarizes the utilization of unreactive C-H bonds in the Pd-catalyzed and ligand-enabled difunctionalization of alkenes.
Pd-Catalyzed and ligand-enabled difunctionalization of olefins through the unreactive C-H bond functionalization of either alkene or their respective coupling partners was summarized. |
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| AbstractList | Palladium-catalyzed and ligand-enabled C-H functionalization methods have emerged as a powerful approach for the preparation of therapeutically important motifs and complex natural products. Olefins, owing to their natural abundance, have been extensively employed for the formation of C-C and C-X bonds and the generation of various heterocycles. Traditionally, activated as well as starting materials with preinstalled functional groups, and also halide substrates under transition metal catalysis, have been employed for olefin difunctionalization. However, strategies for employing unactivated C-H bond functionalization to achieve alkene difunctionalization have rarely been explored. A possible solution to this challenge is the application of bulky ligands which enhances the reductive elimination pathway and inhibits β-hydride elimination to selectively yield difunctionalized alkene products. This feature article summarizes the utilization of unreactive C-H bonds in the Pd-catalyzed and ligand-enabled difunctionalization of alkenes.
Pd-Catalyzed and ligand-enabled difunctionalization of olefins through the unreactive C-H bond functionalization of either alkene or their respective coupling partners was summarized. |
| Author | Kuo, Yao-Haur Barve, Balaji D Li, Wen-Tai |
| AuthorAffiliation | Department of Chemistry National Taiwan Normal University National Research Institute of Chinese Medicine, Ministry of Health and Welfare |
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| ContentType | Journal Article |
| DOI | 10.1039/d1cc04397h |
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| Notes | Dr Yao-Haur Kuo, received his PhD in natural product chemistry, at Chinese Culture University, Taiwan. After that, he conducted postdoctoral research with Prof. K. H. Lee, at Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina at Chapel Hill, U.S.A. In 1992, he joined the National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taiwan, as an assistant research fellow and promoted to research fellow in 2001. His research, interests focus on natural products chemistry, pharmacognosy and quality control of traditional herbs. Balaji D. Barve received his PhD, from Kaohsiung Medical University, Kaohsiung, Taiwan (2014), under the guidance of Professors Jeh-Jeng Wang and Fang-Rong Chang. After post-doctoral work with Professor Lee-Chiang Lo (National Taiwan University, Taipei, Taiwan) and Dr Yao-Haur Kuo (National Research Institute of Chinese Medicine, Taipei, Taiwan). He is currently working with Professor Wenwei Lin (National Taiwan Normal University, Taipei, Taiwan). His research interests include the discovery of novel synthetic methods (metal catalyzed reactions, C-H bond functionalization), glycochemistry and metal free tandem reactions. Wen-Tai Li received his PhD degree in chemistry from National Tsing Hua University in Organometallic chemistry in 1999. Since the summer of 2011, he joined the National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taiwan, as a research fellow. His main research fields include the development of new synthetic methods and transition-metal catalyzed synthesis of bioactive molecules. |
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| References_xml | – issn: 2017 end-page: 453 publication-title: Recent developments in palladium catalyzed natural products synthesis via C-H activation doi: Thrimurtulu Dey Maiti Volla – issn: 2008 end-page: p 353-388 publication-title: Comprehensive Heterocyclic Chemistry III doi: d'Ischia Napolitano Pezzella – issn: 2002 publication-title: Handbook of Organopalladium Chemistry for Organic Synthesis doi: Nigishi – issn: 2007 publication-title: Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals doi: Quin Tyrell – issn: 2011 publication-title: Modern Heterocyclic Chemistry doi: Alvarez-Builla Vaquero Barluenga |
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