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Issue 22, 2018
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One-pot synthesis of 2-naphthols from nitrones and MBH adducts via decarboxylative N–O bond cleavage

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Abstract

The efficient synthesis of 2-naphthols is important for their further development as bioactive compounds and chiral ligands as well as other synthetic purposes. Herein, we describe the unprecedented one-pot synthesis of 2-naphthols through an acid-mediated decarboxylative N–O bond cleavage of bridged benzoxazepine intermediates, which were in turn generated from aryl nitrones and Morita–Baylis–Hillman (MBH) adducts under cationic rhodium(III) catalysis. A range of 2-naphthol derivatives including anthracen-2-ol, phenanthren-2-ol, and 11H-benzo[b]fluoren-7-ol were formed with excellent site selectivities and functional group compatibilities. To gain mechanistic insight into this process, a series of mechanistic investigations and DFT calculations were also performed.

Graphical abstract: One-pot synthesis of 2-naphthols from nitrones and MBH adducts via decarboxylative N–O bond cleavage

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Publication details

The article was received on 11 Sep 2018, accepted on 29 Sep 2018 and first published on 29 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00988K
Citation: Org. Chem. Front., 2018,5, 3210-3218
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    One-pot synthesis of 2-naphthols from nitrones and MBH adducts via decarboxylative N–O bond cleavage

    S. H. Han, A. K. Pandey, H. Lee, S. Kim, D. Kang, Y. H. Jung, H. S. Kim, S. Hong and I. S. Kim, Org. Chem. Front., 2018, 5, 3210
    DOI: 10.1039/C8QO00988K

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