Iron-catalyzed C(sp2)-H bond functionalization with organoboron compounds

Rui Shang; Laurean Ilies; Sobi Asako; Eiichi Nakamura

doi:10.1021/ja5070763

Iron-catalyzed C(sp²)-H bond functionalization with organoboron compounds

Rui Shang, Laurean Ilies, Sobi Asako, Eiichi Nakamura

Graduate School of Natural Science and Technology

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

117 Citations (Scopus)

Abstract

We report here that an iron-catalyzed directed C-H functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the C-H bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.

Original language	English
Pages (from-to)	14349-14352
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	41
DOIs	https://doi.org/10.1021/ja5070763
Publication status	Published - Oct 15 2014

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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AU - Ilies, Laurean

AU - Asako, Sobi

AU - Nakamura, Eiichi

PY - 2014/10/15

Y1 - 2014/10/15

N2 - We report here that an iron-catalyzed directed C-H functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the C-H bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.

AB - We report here that an iron-catalyzed directed C-H functionalization reaction allows the coupling of a variety of aromatic, heteroaromatic, and olefinic substrates with alkenyl and aryl boron compounds under mild oxidative conditions. We rationalize these results by the involvement of an organoiron(III) reactive intermediate that is responsible for the C-H bond-activation process. A zinc salt is crucial to promote the transfer of the organic group from the boron atom to the iron(III) atom.

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