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Issue 15, 2018
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Metal-free benzannulation of yne-allenone esters for atom economical synthesis of functionalized 1-naphthols

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Abstract

A new metal-free benzannulation reaction of yne-allenone esters with H2O by using HOAc as a Lewis acid promoter is reported, providing an atom economical protocol toward aroyl 1-naphthols with good to excellent yields. Exchanging H2O for aromatic amines resulted in iminated Z-1-naphthols with high stereoselectivity in a highly functional-group-compatible manner under mild conditions. The purification of these products only needs to be carried out by washing with 95% EtOH solvent, thereby avoiding traditional chromatography and recrystallization, which belongs to group-assisted purification (GAP) chemistry.

Graphical abstract: Metal-free benzannulation of yne-allenone esters for atom economical synthesis of functionalized 1-naphthols

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Publication details

The article was received on 02 Apr 2018, accepted on 03 Jun 2018 and first published on 05 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC01034J
Citation: Green Chem., 2018,20, 3476-3485
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    Metal-free benzannulation of yne-allenone esters for atom economical synthesis of functionalized 1-naphthols

    H. Sha, F. Liu, J. Lu, Z. Liu, W. Hao, J. Tang, S. Tu and B. Jiang, Green Chem., 2018, 20, 3476
    DOI: 10.1039/C8GC01034J

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