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Issue 28, 2017
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Synthesis of 2,3′-spirobi[indolin]-2-ones enabled by a tandem nucleophilic benzylation/C(sp2)–N cross-coupling reaction sequence

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Abstract

An efficient complementary strategy for the construction of spiro[pyrrolidin-3,2′-oxindole] derivatives has been described. With the sequential nucleophilic benzylation and copper-catalyzed intramolecular C(sp2)–N cross-coupling reaction of 3-aminooxindoles with 2-bromobenzyl bromides, a wide range of 2,3′-spirobi[indolin]-2-ones were smoothly obtained in moderate to good yields. A plausible catalytic cycle for this tandem reaction process was proposed based on the control experiments. This study represents a new perspective for the synthesis of structurally diverse spirocyclic oxindoles by employing 3-aminooxindole substrates.

Graphical abstract: Synthesis of 2,3′-spirobi[indolin]-2-ones enabled by a tandem nucleophilic benzylation/C(sp2)–N cross-coupling reaction sequence

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Publication details

The article was received on 02 Jun 2017, accepted on 26 Jun 2017 and first published on 26 Jun 2017


Article type: Communication
DOI: 10.1039/C7OB01343D
Citation: Org. Biomol. Chem., 2017,15, 5887-5892
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    Synthesis of 2,3′-spirobi[indolin]-2-ones enabled by a tandem nucleophilic benzylation/C(sp2)–N cross-coupling reaction sequence

    B. Cui, J. Shan, C. Yuan, W. Han, N. Wan and Y. Chen, Org. Biomol. Chem., 2017, 15, 5887
    DOI: 10.1039/C7OB01343D

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