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Synthesis of branched and linear aryl allylic alcohols: C[sbnd]H bond allylation of 2-aryl-3H-indoles with vinyl cyclic carbonates.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Sep2024, Vol. 147, pN.PAG-N.PAG. 1p. - Publication Year :
- 2024
-
Abstract
- [Display omitted] • Effective synthesis of branched and linear allyl arenes. • Excellent E/Z selectivity and regio-selectivity. • Easily available starting materials, mild and redox-neutral reaction conditions. Presented herein is an effective synthesis of branched and linear allyl arenes based on the reactions of 2-aryl-3 H -indoles with 5-methylene-1,3-dioxan-2-one or 4-vinyl-1,3-dioxolan-2-one. Mechanistically, the reactions are initiated by Rh(III)-catalyzed aryl C(sp2)–H bond activation/cyclometallation followed by vinyl coordination/migratory insertion and β–O elimination through release of CO 2 as the only by-product. By using this newly developed protocol, a group of 2-aryl-3 H -indole derivatives bearing the substructure of either branched or linear allylic alcohol were obtained in good efficiency. Notably, the linear allylic alcohols were obtained with excellent E/Z selectivity when unsubstituted vinyl-1,3-dioxolan-2-one was used as the allyl surrogate. With advantages such as easily available starting materials, mild and redox-neutral reaction conditions, good compatibility with a broad range of functional groups, benign solvent and divergent products, this protocol is expected to be used in the synthesis of indole-based functional molecules. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 147
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 179025668
- Full Text :
- https://doi.org/10.1016/j.tetlet.2024.155225