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Issue 17, 2018
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Bismuth(III)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans

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Abstract

2-(Hetero)aryl tetrahydrofurans and tetrahydropyrans were successfully synthesized using Bi(OTf)3-catalyzed hydroalkoxylation (cycloisomerization) of alkynols (via 5 or 6 exo-dig cyclization) and intermolecular (hetero)arylation. This reaction involves a highly efficient cascade process, where initially the alkynol undergoes a cycloisomerization step via activation of the triple bond and generates the oxocarbenium ion, which subsequently participates in the (hetero)hydroarylation step with electron-rich arenes. Simple to complex suitably functionalized alkynols (4-pentyn-1-ols and 5-hexyn-1-ols) and electron-rich aromatic compounds were found to be reliable substrates in this cascade transformation and furnished a wide range of oxygen heterocycles. This practical tandem process provides a means to build libraries related to pharmacologically active molecules and natural product like scaffolds.

Graphical abstract: Bismuth(iii)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans

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Publication details

The article was received on 12 Feb 2018, accepted on 06 Apr 2018 and first published on 06 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00368H
Citation: Org. Biomol. Chem., 2018,16, 3229-3240
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    Bismuth(III)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans

    A. K. Nakate, M. S. Pratapure and R. Kontham, Org. Biomol. Chem., 2018, 16, 3229
    DOI: 10.1039/C8OB00368H

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