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Trisannulation of benzamides and cyclohexadienone-tethered 1,1-disubstituted allenes initiated by Cp*Rh(III)-catalyzed C–H activation

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Abstract

A diastereoselectively pure trisannulation of N-(pivaloyloxy)benzamides and newly synthesized cyclohexadienone-tethered 1,1-disubstituted allenes has been successfully established via the initiation of Cp*Rh(III)-catalyzed C–H bond activation. The tandem reaction, involving a formal Cp*Rh(III)-catalyzed [4 + 2]-annulation, a relay ene reaction, and an intramolecular aza-Michael-addition sequence, proceeds smoothly at room temperature to deliver the special trisannulation products with high to excellent yields (up to 96%). Furthermore, the gram-scale reaction and post-transformation are also presented.

Graphical abstract: Trisannulation of benzamides and cyclohexadienone-tethered 1,1-disubstituted allenes initiated by Cp*Rh(iii)-catalyzed C–H activation

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Publication details

The article was received on 27 Nov 2018, accepted on 25 Jan 2019 and first published on 29 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01279B
Citation: Org. Chem. Front., 2019, Advance Article

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    Trisannulation of benzamides and cyclohexadienone-tethered 1,1-disubstituted allenes initiated by Cp*Rh(III)-catalyzed C–H activation

    D. Kong, Y. Wang, Y. Tan, J. Zhang, J. Zhang, P. Tian and G. Lin, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01279B

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