Iron promoted conjugate addition: implication of the six-centered mechanism based on the isolation of the iron-enolate intermediate

Daisuke Noda; Yusuke Sunada; Takuji Hatakeyama; Masaharu Nakamura; Hideo Nagashima

doi:10.1039/C2CC37144H

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Chemical Communications

Issue 100, 2012

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Iron promoted conjugate addition: implication of the six-centered mechanism based on the isolation of the iron-enolate intermediate

Daisuke Noda,^a Yusuke Sunada,^a^b Takuji Hatakeyama,^c Masaharu Nakamura^c and Hideo Nagashima*^a^b

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Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga, Fukuoka, Japan

Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga, Fukuoka, Japan
E-mail: nagasima@cm.kyushu-u.ac.jp ;
Fax: +81 92-583-7819 ;
Tel: +81 92-583-7819

International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

Chem. Commun., 2012,48, 12231-12233

DOI: 10.1039/C2CC37144H
Received 01 Oct 2012, Accepted 01 Nov 2012
First published online 02 Nov 2012

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Treatment of (η¹-mesityl)₂Fe(κ²-TMEDA) (1′) with an α,β-unsaturated carbonyl compound results in 1,4-addition of the mesityl group to give an iron enolate 3 quantitatively. The Z-configuration of the enolate suggested the six-centered mechanism for the conjugate addition.

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Daisuke Noda
Yusuke Sunada
Takuji Hatakeyama
Masaharu Nakamura
Hideo Nagashima

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Iron promoted conjugate addition: implication of the six-centered mechanism based on the isolation of the iron-enolate intermediate

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