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Directing group assisted rhodium catalyzed meta-C–H alkynylation of arenes
Site-selective C–H alkynylation of arenes to produce aryl alkynes is a highly desirable transformation due to the prevalence of aryl alkynes in various natural products, drug molecules and in materials. To ensure site-selective C–H functionalization, directing group (DG) assisted C–H activation has...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9116288/ https://www.ncbi.nlm.nih.gov/pubmed/35694332 http://dx.doi.org/10.1039/d2sc00982j |
Sumario: | Site-selective C–H alkynylation of arenes to produce aryl alkynes is a highly desirable transformation due to the prevalence of aryl alkynes in various natural products, drug molecules and in materials. To ensure site-selective C–H functionalization, directing group (DG) assisted C–H activation has been evolved as a useful synthetic tool. In contrast to DG-assisted ortho-C–H activation, distal meta-C–H activation is highly challenging and has attracted significant attention in recent years. However, developments are majorly focused on Pd-based catalytic systems. In order to diversify the scope of distal meta-C–H functionalization, herein we disclosed the first Rh(i) catalyzed meta-C–H alkynylation protocol through the inverse Sonogashira coupling reaction. The protocol is compatible with various substrate classes which include phenylacetic acids, hydrocinnamic acids, 2-phenyl benzoic acids, 2-phenyl phenols, benzyl sulfonates and ether-based scaffolds. The post-synthetic modification of meta-alkynylated arenes is also demonstrated through DG-removal as well as functional group interconversion. |
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