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Rhodium III -catalyzed remote difunctionalization of arenes assisted by a relay directing group.
- Source :
-
Chemical science [Chem Sci] 2022 May 30; Vol. 13 (24), pp. 7347-7354. Date of Electronic Publication: 2022 May 30 (Print Publication: 2022). - Publication Year :
- 2022
-
Abstract
- Rhodium-catalyzed diverse tandem twofold C-H bond activation reactions of para -olefin-tethered arenes have been realized, with unsaturated reagents such as internal alkynes, dioxazolones, and isocyanates being the coupling partner as well as a relay directing group which triggers cyclization of the para -olefin group under oxidative or redox-neutral conditions. The reaction proceeded via initial ortho -C-H activation assisted by a built-in directing group in the arene, and the ortho -incorporation of the unsaturated coupling partner simultaneously generated a relay directing group that allows sequential C-H activation at the meta -position and subsequent cyclization of the para -olefins. The overall reaction represents C-C or N-C difunctionalization of the arene with the generation of diverse 2,3-dihydrobenzofuran platforms. The catalytic system proceeded with good efficiency, simple reaction conditions, and broad substrate scope. The diverse transformations of the products demonstrated the synthetic utility of this tandem reaction.<br />Competing Interests: The authors declare no competing financial interest.<br /> (This journal is © The Royal Society of Chemistry.)
Details
- Language :
- English
- ISSN :
- 2041-6520
- Volume :
- 13
- Issue :
- 24
- Database :
- MEDLINE
- Journal :
- Chemical science
- Publication Type :
- Academic Journal
- Accession number :
- 35799802
- Full Text :
- https://doi.org/10.1039/d2sc02205b