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Rhodium-catalyzed synthesis of C4-chalcogenoalkylated oxindoles via Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones

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Abstract

Efficient rhodium-catalyzed Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones with α-thioesters has been accomplished for the synthesis of C4-thioalkylated oxindoles. The developed reaction offers the selective functionalization of C4-position of oxindole via generation of S-ylide and [2, 3]-sigmatropic rearrangement and allows access to diverse C4-thioalkylated oxindoles in good to excellent yield. Furthermore, the method was successfully extended to the synthesis C4-selenoalkylated oxindoles employing the corresponding α-selenoester.

Graphic abstract

Efficient rhodium-catalyzed Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones with α-thio/α-seleno-esters have been disclosed for the synthesis of C4-thio/selenoalkylated oxindoles.

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Acknowledgements

We thank DST-SERB (EMR/2016/003677) for the financial support and DST-FIST for ESI-MS facility. ACSR thanks the Council of Scientific & Industrial Research (CSIR) for fellowship.

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  1. Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600 036, Tamilnadu, India

    Angula Chandra Shekar Reddy, Bhojkumar Nayak & Pazhamalai Anbarasan

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  1. Angula Chandra Shekar Reddy
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  2. Bhojkumar Nayak
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  3. Pazhamalai Anbarasan
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Correspondence to Pazhamalai Anbarasan.

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Reddy, A.C.S., Nayak, B. & Anbarasan, P. Rhodium-catalyzed synthesis of C4-chalcogenoalkylated oxindoles via Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones. J Chem Sci 131, 119 (2019). https://doi.org/10.1007/s12039-019-1711-9

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