Iron-catalyzed ortho -allylation of aromatic carboxamides with allyl ethers

Sobi Asako; Laurean Ilies; Eiichi Nakamura

doi:10.1021/ja4106368

Iron-catalyzed ortho -allylation of aromatic carboxamides with allyl ethers

Sobi Asako, Laurean Ilies, Eiichi Nakamura

Graduate School of Natural Science and Technology

Research output: Contribution to journal › Article › peer-review

200 Citations (Scopus)

Abstract

Arenes possessing an N-(quinolin-8-yl)amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in γ-selective fashion.

Original language	English
Pages (from-to)	17755-17757
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	135
Issue number	47
DOIs	https://doi.org/10.1021/ja4106368
Publication status	Published - Nov 27 2013

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja4106368

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title = "Iron-catalyzed ortho -allylation of aromatic carboxamides with allyl ethers",

abstract = "Arenes possessing an N-(quinolin-8-yl)amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in γ-selective fashion.",

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AU - Ilies, Laurean

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N2 - Arenes possessing an N-(quinolin-8-yl)amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in γ-selective fashion.

AB - Arenes possessing an N-(quinolin-8-yl)amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in γ-selective fashion.

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Iron-catalyzed ortho -allylation of aromatic carboxamides with allyl ethers

Abstract

ASJC Scopus subject areas

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