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The study of metal-free and palladium-catalysed synthesis of benzochromenes via direct C–H arylation using unactivated aryl benzyl ethers derived from essential oils as raw materials

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Abstract

The synthesis of 6H-benzo[c]chromenes from unactivated 2-bromo aryl benzyl ethers was studied through two approaches: (i) the transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution; and (ii) the intramolecular cyclization via direct C–H arylation catalysed by PdCl2(MeCN)2. Having developed the most efficient method, a 17-membered chromene library was prepared in good yields and in shorter reaction times starting from commercially available phenol derivatives and phenol-rich essential oils (Eugenia caryophyllys and Plectranthus amboinicus) as raw materials, proving how sustainable and eco-friendly our protocol is. Additionally, the ruggedness of the optimized reaction conditions was evaluated with N-benzylanilines, giving the respective phenanthridone as an unexpected product, while the metal-free oxidation of the obtained 6H-benzo[c]chromenes was also performed to furnish the benzocoumarins.

Graphical abstract: The study of metal-free and palladium-catalysed synthesis of benzochromenes via direct C–H arylation using unactivated aryl benzyl ethers derived from essential oils as raw materials

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Publication details

The article was received on 24 Mar 2017, accepted on 19 May 2017 and first published on 24 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00232G
Citation: Org. Chem. Front., 2017, Advance Article
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    The study of metal-free and palladium-catalysed synthesis of benzochromenes via direct C–H arylation using unactivated aryl benzyl ethers derived from essential oils as raw materials

    M. C. Ortiz Villamizar, F. I. Zubkov, C. E. Puerto Galvis, L. Y. Vargas Méndez and V. V. Kouznetsov, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00232G

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