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Rhodium-catalyzed decarbonylative cycloadditions of 1H-indene-1,2,3-triones and alkynes via direct C–C bond activation: divergent synthesis of indenones and quinones
- Source :
- Organic Chemistry Frontiers. 5:1613-1621
- Publication Year :
- 2018
- Publisher :
- Royal Society of Chemistry (RSC), 2018.
-
Abstract
- A one-step preparation method for indenone and quinone derivatives via rhodium-mediated [5 + 2 − 2] and [5 + 2 − 1] decarbonylative cycloadditions of 1H-indene-1,2,3-triones and alkynes has been achieved. A rhodium(I) complex, [Rh(COD)Cl]2, with a bisphosphine rac-BINAP ligand was the most efficient catalytic system for this decarbonylative cycloaddition transformation. The [5 + 2 − 2] and [5 + 2 − 1] transformation processes can be enhanced by respectively adding copper chloride or hexacarbonyl chromium as an additive. This reaction is suitable for a broad range of alkynes and 1H-indene-1,2,3-triones and a variety of fused indenone and quinone derivatives were obtained in medium to high yields. More importantly, this work provides a new model for the direct activation of C–C bonds in less strained ketones without auxiliary groups.
Details
- ISSN :
- 20524129
- Volume :
- 5
- Database :
- OpenAIRE
- Journal :
- Organic Chemistry Frontiers
- Accession number :
- edsair.doi...........377b599c93ecbe975373c4a387c3ed83