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A cascade process for the synthesis of ortho-formyl allyl aryl ethers and 2H-chromen-2-ol derivatives from arynes via trapping of o-quinone methide with an activated alkene

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Abstract

A transition-metal free synthetic strategy has been developed for the direct synthesis of ortho-formyl substituted allyl aryl ethers via a cascade three-component coupling of arynes, activated alkene and N,N-dimethylformamide. The reaction proceeds via C–O and C–C bond cleavage as well as C–C and two new C–O bond formations in a single reaction vessel. The methodology provides a good yield of ortho-formyl substituted allyl aryl ethers. Moreover, the synthetic strategy has been utilized for the one-pot synthesis of 2H-chromen-2-ol derivatives.

Graphical abstract: A cascade process for the synthesis of ortho-formyl allyl aryl ethers and 2H-chromen-2-ol derivatives from arynes via trapping of o-quinone methide with an activated alkene

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Publication details

The article was received on 10 Oct 2018, accepted on 07 Dec 2018 and first published on 08 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02507J
Citation: Org. Biomol. Chem., 2019, Advance Article
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    A cascade process for the synthesis of ortho-formyl allyl aryl ethers and 2H-chromen-2-ol derivatives from arynes via trapping of o-quinone methide with an activated alkene

    A. Sharma and P. Gogoi, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02507J

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