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Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles

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Abstract

Herein a previously unreported catalyst-free SN1 reaction of the 3-halooxindoles to build 3-functionalized-2-oxindoles is described. The present protocol utilizes the thermal-mediated heterolytic cleavage of the 3-halooxindoles to generate a highly electrophilic 1-H-o-azaxylylene-1-ium A or 1-alkyl-o-azaxylylene-1-ium B intermediate as the Michael acceptor, avoiding the utilization of an additional base and metal as promoters, and providing a diversity-oriented approach to a series of 3-functionalized-2-oxindoles bearing a tetrasubstituted center in high yields (up to 93% yield). This method could provide libraries of structurally diverse and medicinally important small molecules that could aid the search for new bioactive molecules.

Graphical abstract: Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles

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Publication details

The article was received on 12 Nov 2018, accepted on 05 Dec 2018 and first published on 05 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01222A
Citation: Org. Chem. Front., 2018, Advance Article
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    Thermal-mediated catalyst-free heterolytic cleavage of 3-halooxindoles: rapid access to 3-functionalized-2-oxindoles

    X. Liu, J. Yue, S. Chen, H. Liu, K. Yang, T. Feng and Y. Zhou, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO01222A

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