Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications
Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, and advanced materials. Significant efforts have been made toward the development of new and practical methods to access this important class of compounds by selectively activating the alkenyl C(sp2)...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2023
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| Online Access: | https://hdl.handle.net/10356/171496 |
| _version_ | 1824454302007033856 |
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| author | Lu, Ming-Zhu Goh, Jeffrey Maraswami, Manikantha Jia, Zhenhua Tian, Jie-Sheng Loh, Teck-Peng |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Lu, Ming-Zhu Goh, Jeffrey Maraswami, Manikantha Jia, Zhenhua Tian, Jie-Sheng Loh, Teck-Peng |
| author_sort | Lu, Ming-Zhu |
| collection | NTU |
| description | Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, and advanced materials. Significant efforts have been made toward the development of new and practical methods to access this important class of compounds by selectively activating the alkenyl C(sp2)-H bonds in recent years. In this comprehensive review, we describe the state-of-the-art strategies for the direct functionalization of alkenyl sp2 C-H and C-F bonds until June 2022. Moreover, metal-free, photoredox, and electrochemical strategies are also covered. For clarity, this review has been divided into two parts; the first part focuses on currently available alkenyl sp2 C-H functionalization methods using different alkene derivatives as the starting materials, and the second part describes the alkenyl sp2 C-F bond functionalization using easily accessible gem-difluoroalkenes as the starting material. This review includes the scope, limitations, mechanistic studies, stereoselective control (using directing groups as well as metal-migration strategies), and their applications to complex molecule synthesis where appropriate. Overall, this comprehensive review aims to document the considerable advancements, current status, and emerging work by critically summarizing the contributions of researchers working in this fascinating area and is expected to stimulate novel, innovative, and broadly applicable strategies for alkenyl sp2 C-H and C-F bond functionalizations in the coming years. |
| first_indexed | 2025-02-19T03:20:09Z |
| format | Journal Article |
| id | ntu-10356/171496 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:20:09Z |
| publishDate | 2023 |
| record_format | dspace |
| spelling | ntu-10356/1714962024-06-21T15:31:59Z Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications Lu, Ming-Zhu Goh, Jeffrey Maraswami, Manikantha Jia, Zhenhua Tian, Jie-Sheng Loh, Teck-Peng School of Chemistry, Chemical Engineering and Biotechnology Chemistry Alkenyl C-F Bonds Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, and advanced materials. Significant efforts have been made toward the development of new and practical methods to access this important class of compounds by selectively activating the alkenyl C(sp2)-H bonds in recent years. In this comprehensive review, we describe the state-of-the-art strategies for the direct functionalization of alkenyl sp2 C-H and C-F bonds until June 2022. Moreover, metal-free, photoredox, and electrochemical strategies are also covered. For clarity, this review has been divided into two parts; the first part focuses on currently available alkenyl sp2 C-H functionalization methods using different alkene derivatives as the starting materials, and the second part describes the alkenyl sp2 C-F bond functionalization using easily accessible gem-difluoroalkenes as the starting material. This review includes the scope, limitations, mechanistic studies, stereoselective control (using directing groups as well as metal-migration strategies), and their applications to complex molecule synthesis where appropriate. Overall, this comprehensive review aims to document the considerable advancements, current status, and emerging work by critically summarizing the contributions of researchers working in this fascinating area and is expected to stimulate novel, innovative, and broadly applicable strategies for alkenyl sp2 C-H and C-F bond functionalizations in the coming years. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) Nanyang Technological University Submitted/Accepted version We gratefully acknowledge the financial support from Distinguished University Professor grant (Nanyang Technological University), AcRF Tier1 grants from the Ministry of Education of Singapore (RG11/20 and RT14/20), and the Agency for Science, Technology and Research (A*STAR) under its MTC Individual Research Grants( M21K2c0114). We also gratefully acknowledge the financial support from the National Natural Science Foundation of China (no.22101095). 2023-11-03T01:42:43Z 2023-11-03T01:42:43Z 2022 Journal Article Lu, M., Goh, J., Maraswami, M., Jia, Z., Tian, J. & Loh, T. (2022). Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications. Chemical Reviews, 122(24), 17479-17646. https://dx.doi.org/10.1021/acs.chemrev.2c00032 0009-2665 https://hdl.handle.net/10356/171496 10.1021/acs.chemrev.2c00032 36240299 2-s2.0-85140232447 24 122 17479 17646 en RG11/20 RT14/20 M21K2c0114 Chemical Reviews © 2022 American Chemical Society. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1021/acs.chemrev.2c00032. application/pdf |
| spellingShingle | Chemistry Alkenyl C-F Bonds Lu, Ming-Zhu Goh, Jeffrey Maraswami, Manikantha Jia, Zhenhua Tian, Jie-Sheng Loh, Teck-Peng Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications |
| title | Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications |
| title_full | Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications |
| title_fullStr | Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications |
| title_full_unstemmed | Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications |
| title_short | Recent advances in alkenyl sp² C-H and C-F bond functionalizations: scope, mechanism, and applications |
| title_sort | recent advances in alkenyl sp² c h and c f bond functionalizations scope mechanism and applications |
| topic | Chemistry Alkenyl C-F Bonds |
| url | https://hdl.handle.net/10356/171496 |
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