Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation
Macrocycles are commonly synthesized via late-stage macrolactamization and macrolactonization. Strategies involving C–C bond macrocyclization have been reported, and examples include the transition-metal-catalyzed ring-closing metathesis and coupling reactions. In this mini-review, we summarize the...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/13/2/438 |
| _version_ | 1797621817556336640 |
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| author | Xiao Wang Ming-Zhu Lu Teck-Peng Loh |
| author_facet | Xiao Wang Ming-Zhu Lu Teck-Peng Loh |
| author_sort | Xiao Wang |
| collection | DOAJ |
| description | Macrocycles are commonly synthesized via late-stage macrolactamization and macrolactonization. Strategies involving C–C bond macrocyclization have been reported, and examples include the transition-metal-catalyzed ring-closing metathesis and coupling reactions. In this mini-review, we summarize the recent progress in the direct synthesis of polyketide and polypeptide macrocycles using a transition-metal-catalyzed C–H bond activation strategy. In the first part, rhodium-catalyzed alkene–alkene ring-closing coupling for polyketide synthesis is described. The second part summarizes the synthesis of polypeptide macrocycles. The activation of indolyl and aryl C(sp<sup>2</sup>)–H bonds followed by coupling with various coupling partners such as aryl halides, arylates, and alkynyl bromide is then documented. Moreover, transition-metal-catalyzed C–C bond macrocyclization reactions via alkyl C(sp<sup>3</sup>)–H bond activation are also included. We hope that this mini-review will inspire more researchers to explore new and broadly applicable strategies for C–C bond macrocyclization via intramolecular C–H activation. |
| first_indexed | 2024-03-11T09:01:23Z |
| format | Article |
| id | doaj.art-dcea92ec20594668980773d0475f02b2 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T09:01:23Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-dcea92ec20594668980773d0475f02b22023-11-16T19:43:11ZengMDPI AGCatalysts2073-43442023-02-0113243810.3390/catal13020438Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond ActivationXiao Wang0Ming-Zhu Lu1Teck-Peng Loh2Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, ChinaCollege of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, ChinaInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, ChinaMacrocycles are commonly synthesized via late-stage macrolactamization and macrolactonization. Strategies involving C–C bond macrocyclization have been reported, and examples include the transition-metal-catalyzed ring-closing metathesis and coupling reactions. In this mini-review, we summarize the recent progress in the direct synthesis of polyketide and polypeptide macrocycles using a transition-metal-catalyzed C–H bond activation strategy. In the first part, rhodium-catalyzed alkene–alkene ring-closing coupling for polyketide synthesis is described. The second part summarizes the synthesis of polypeptide macrocycles. The activation of indolyl and aryl C(sp<sup>2</sup>)–H bonds followed by coupling with various coupling partners such as aryl halides, arylates, and alkynyl bromide is then documented. Moreover, transition-metal-catalyzed C–C bond macrocyclization reactions via alkyl C(sp<sup>3</sup>)–H bond activation are also included. We hope that this mini-review will inspire more researchers to explore new and broadly applicable strategies for C–C bond macrocyclization via intramolecular C–H activation.https://www.mdpi.com/2073-4344/13/2/438transition-metal catalysisC–H activationmacrocyclizationpolyketide macrocyclespolypeptide macrocycles |
| spellingShingle | Xiao Wang Ming-Zhu Lu Teck-Peng Loh Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation Catalysts transition-metal catalysis C–H activation macrocyclization polyketide macrocycles polypeptide macrocycles |
| title | Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation |
| title_full | Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation |
| title_fullStr | Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation |
| title_full_unstemmed | Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation |
| title_short | Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation |
| title_sort | transition metal catalyzed c c bond macrocyclization via intramolecular c h bond activation |
| topic | transition-metal catalysis C–H activation macrocyclization polyketide macrocycles polypeptide macrocycles |
| url | https://www.mdpi.com/2073-4344/13/2/438 |
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