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KOH-catalyzed cross-coupling of primary and secondary alcohols: evidence for radical pathways

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Abstract

A simple base, KOH-catalyzed cross-coupling of primary and secondary alcohols is reported in which the primary alcohols play the role of alkylation reagents. EPR and mechanistic studies confirmed the involvement of radical and ketone intermediates formed from primary and secondary alcohols, respectively, leading to the formation of β-alkylated secondary alcohols.

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A simple base-catalyzed synthesis of higher secondary alcohols directly from the cross-coupling of primary and secondary alcohols is reported.

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Acknowledgements

We thank SERB New Delhi (CRG/2021/001706), DAE and NISER for financial support. A.S.N., S.J. and M.K.S. thank DAE for fellowships.

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  1. Amlan Subhadarshi Nayak and Shubham Jaiswal contributed equally.

Authors and Affiliations

  1. School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, 752 050, India

    Amlan Subhadarshi Nayak, Shubham Jaiswal, Manas Kumar Sahu & Chidambaram Gunanathan

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  1. Amlan Subhadarshi Nayak
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  3. Manas Kumar Sahu
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Correspondence to Chidambaram Gunanathan.

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Nayak, A.S., Jaiswal, S., Sahu, M.K. et al. KOH-catalyzed cross-coupling of primary and secondary alcohols: evidence for radical pathways. J Chem Sci 136, 5 (2024). https://doi.org/10.1007/s12039-023-02241-7

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