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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 21 Feb 2018, accepted on 20 Mar 2018 and first published on 28 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00186C
Citation: Org. Chem. Front., 2018, Advance Article
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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

    W. Guo, S. Wu, T. Wang, Q. Xie, Y. Duan, S. Luo, J. Wang and X. Yu, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00186C

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