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Directing group assisted para-selective C–H alkynylation of unbiased arenes enabled by rhodium catalysis
Regioselective C–H alkynylation of arenes via C–H activation is challenging yet a highly desirable transformation. In this regard, directing group assisted C(sp(2))–H alkynylation of arenes offers a unique opportunity to ensure precise regioselectivity. While the existing methods are mainly centered...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599460/ https://www.ncbi.nlm.nih.gov/pubmed/37886091 http://dx.doi.org/10.1039/d3sc03528j |
Sumario: | Regioselective C–H alkynylation of arenes via C–H activation is challenging yet a highly desirable transformation. In this regard, directing group assisted C(sp(2))–H alkynylation of arenes offers a unique opportunity to ensure precise regioselectivity. While the existing methods are mainly centered around ortho-C–H alkynylation and a few for meta-C–H alkynylation, the DG-assisted para-selective C–H alkynylation is yet to be reported. Herein we disclose the first report on Rh-catalyzed para-C–H alkynylation of sterically and electronically unbiased arenes. The para-selectivity is achieved with the assistance of a cyano-based directing template and the selectivity remained unaltered irrespective of the steric and electronic influence of the substituents. The post-synthetic modification of synthesized para-alkynylated arenes is also demonstrated. The mechanistic intricacies of the developed protocol are elucidated through experimental and computational studies. |
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