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Issue 16, 2018
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Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives

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Abstract

An efficient tris(4-methoxyphenyl)phosphine-catalyzed domino reaction between γ-benzyl allenoates and ethyl (Z)-2-(3-oxobenzo[b]thiophen-2(3H)-ylidene)acetate has been developed, which produces a series of 2H-benzo[4,5]thieno[3,2-b]pyran derivatives in high yields. The substrate scope includes both electron-withdrawing (e.g., halogen) and electron-donating (e.g., methoxy) groups on both the benzothiophene and allenoate moieties. The reaction can also be performed on the gram scale with good yield (e.g., 77%). In this reaction, γ-substituted allenoate acts as a two-carbon synthon, in a manner rarely reported in the literature to date.

Graphical abstract: Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives

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Publication details

The article was received on 02 Jan 2018, accepted on 27 Mar 2018 and first published on 27 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00004B
Citation: Org. Biomol. Chem., 2018,16, 2885-2892
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    Phosphine-catalyzed [4 + 2] annulation of γ-benzyl allenoates: facile synthesis of benzothieno[3,2-b]pyran derivatives

    S. Ma, A. Yu and X. Meng, Org. Biomol. Chem., 2018, 16, 2885
    DOI: 10.1039/C8OB00004B

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