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Ru-catalysed C(sp 2 )-H vinylation/annulation of benzoic acids and alkynes: rapid access to medium-sized lactones.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2021 Jan 28; Vol. 57 (9), pp. 1113-1116. Date of Electronic Publication: 2021 Jan 07. - Publication Year :
- 2021
-
Abstract
- An unprecedented ruthenium catalysed [4+4] annulation of readily available benzoic acids and alkynes is reported for the first time. The carboxylate group acts as both a directing group and an internal nucleophilic reagent to facilitate a C(sp <superscript>2</superscript> )-H vinylation/annulation cascade. This reaction avoids the classically oxidative [4+2] annulation, allowing the efficient synthesis of a wide array of eight-membered lactones under oxidant-free conditions. Moreover, this catalytic system can be successfully extended to [4+3] and [4+5] annulations for the assembly of seven- and nine-membered lactones.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 57
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 33410434
- Full Text :
- https://doi.org/10.1039/d0cc07573f