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Issue 23, 2018
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A new dehydrogenative [4 + 1] annulation between para-quinone methides (p-QMs) and iodonium ylides for the synthesis of 2,3-dihydrobenzofurans

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Abstract

A new dehydrogenative [4 + 1] annulation of para-quinone methides (p-QMs) with acyclic and cyclic phenyl iodonium ylides has been established, delivering a variety of functionalized 2,3-dihydrobenzofurans with the retention of the quinone methide unit in generally good yields. The reaction pathway involves 1,6-nucleophilic addition, nucleophilic substitution and oxidation under mild metal-free and convenient conditions, and provides a practical access to construct benzofuran frameworks.

Graphical abstract: A new dehydrogenative [4 + 1] annulation between para-quinone methides (p-QMs) and iodonium ylides for the synthesis of 2,3-dihydrobenzofurans

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Publication details

The article was received on 02 Sep 2018, accepted on 23 Oct 2018 and first published on 25 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00950C
Citation: Org. Chem. Front., 2018,5, 3483-3487

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    A new dehydrogenative [4 + 1] annulation between para-quinone methides (p-QMs) and iodonium ylides for the synthesis of 2,3-dihydrobenzofurans

    Y. Xiong, S. Shi, W. Hao, S. Tu and B. Jiang, Org. Chem. Front., 2018, 5, 3483
    DOI: 10.1039/C8QO00950C

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