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Synlett
DOI: 10.1055/a-2796-8915
Letter

Carbenoid and Vinylogous Reactivity of Diazo Arylidene Succinimide (DAS) with Benzyl Aryl Thioethers under Rhodium Catalysis

Authors

  • Abhinav Joshi

    1   Department of Chemistry, Indian Institute of Science Education and Research Pune, Pune, India (Ringgold ID: RIN193158)

  • Onkar S. Bankar

    1   Department of Chemistry, Indian Institute of Science Education and Research Pune, Pune, India (Ringgold ID: RIN193158)

  • Chhabi Pal

    1   Department of Chemistry, Indian Institute of Science Education and Research Pune, Pune, India (Ringgold ID: RIN193158)

  • Bhavya Dhamyan

    1   Department of Chemistry, Indian Institute of Science Education and Research Pune, Pune, India (Ringgold ID: RIN193158)

  • Dr. Ramakrishna G. G. Bhat 

    2   Chemistry, Indian Institute of Science Education and Research Pune, Pune, India (Ringgold ID: RIN193158)

Supported by: ANRF (formerly known as SERB), Department of Science and Technology (SERB-DST), New Delhi, Government of India (File no: CRG/2023/004226) CRG/2023/004226
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Herein, we have explored the reactivity of diazo arylidene succinimide (DAS) with benzyl thioether to achieve [1,2]/[1,4]-Stevens rearrangement via rhodium catalysis. The protocol has successfully demonstrated the substituent dependent competitive reactivity of DAS to tune the ratio of [1,2]-Stevens and [1,4]-Stevens rearrangement products. The protocol facilitated the formation of C-C and C-S bonds between carbenoid/vinylogous center. This catalytic protocol works smoothly in environmentally benign solvent to afford the corresponding desired products in moderate to good yields. The protocol proved to be scalable on gram quantity.



Publication History

Received: 22 October 2025

Accepted after revision: 25 January 2026

Accepted Manuscript online:
31 January 2026

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