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Carboxylate-directed C-H allylation with allyl alcohols or ethers.

ABSTRACT: A [Ru(p-cymene)Cl₂]₂ catalyst activates allyl alcohols and ethers for the regioselective ortho-C-H allylation of aromatic and heteroaromatic carboxylates. The reaction is orthogonal to most C-H functionalisations with allyl alcohols in that allyl arenes rather than carbonyl compounds are obtained. A wide range of substrates are thus smoothly transformed to allylarenes at 50 °C in phosphate-buffered 2,2,2-trichloroethanol. The reaction concept combines the use of abundant reagents and directing groups in a sustainable, waste-minimised method for C-C bond formation.

SUBMITTER: Hu XQ

PROVIDER: S-EPMC6001406 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Carboxylate-directed C-H allylation with allyl alcohols or ethers.

Hu Xiao-Qiang XQ Hu Zhiyong Z Trita A Stefania AS Zhang Guodong G Gooßen Lukas J LJ

Chemical science 20180521 23

A [Ru(p-cymene)Cl2]2 catalyst activates allyl alcohols and ethers for the regioselective ortho-C-H allylation of aromatic and heteroaromatic carboxylates. The reaction is orthogonal to most C-H functionalisations with allyl alcohols in that allyl arenes rather than carbonyl compounds are obtained. A wide range of substrates are thus smoothly transformed to allylarenes at 50 °C in phosphate-buffered 2,2,2-trichloroethanol. The reaction concept combines the use ...[more]

PMID: 29997885

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