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Domino ring opening and selective O/S-alkylation of cyclic ethers and thioethers

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Abstract

Chemoselective domino ring opening and selective O/S-alkylation of ethers/thioethers over enol C/O alkylation has been observed. Various 2-aryl chromanones/thiochromanones with alkyl/allyl bromides were smoothly converted into the corresponding highly functionalized ethers and thioethers in excellent yields with high selectivity.

Graphic abstract

An unusual, chemoselective domino ring opening and selective ether/thioether O/S-alkylation over. An unusual, chemoselective domino ring opening and selective ether/thioether O/S alkylation over enol C/O alkylation has been observed.

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  49. CCDC number for the crystal structure 6r is 1867343

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Acknowledgements

V. A. thank CSIR, New Delhi, for Senior Research Fellowship (SRF). TTR thanks UGC for the scholarship. We also acknowledge the Central Instrumentation Facility (CIF), Pondicherry University, for NMR spectra and DST-FIST for the ESI-HRMS facility.

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Science and Engineering Research Board (DST-SERB [No. EEQ/2018/000930]).

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Authors and Affiliations

  1. Department of Chemistry, Pondicherry University, Pondicherry, 605 014, India

    Manickam Bakthadoss, Vishal Agarwal, Thirupathi Reddy Tadiparthi & Mushaf Mohammad

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  1. Manickam Bakthadoss
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  2. Vishal Agarwal
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  3. Thirupathi Reddy Tadiparthi
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  4. Mushaf Mohammad
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Correspondence to Manickam Bakthadoss.

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Bakthadoss, M., Agarwal, V., Tadiparthi, T.R. et al. Domino ring opening and selective O/S-alkylation of cyclic ethers and thioethers. Mol Divers 25, 2467–2478 (2021). https://doi.org/10.1007/s11030-020-10105-2

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