Issue 10, 2014
From the journal:

New Journal of Chemistry

Stoichiometric formation of conjugated dienyl ketones from 1,3-dienes and ketenes at a ruthenium(0) centre†

Masafumi Hirano,*ab   Takuya Okamoto,a   Nobuyuki Komineab  and  Sanshiro Komiya‡a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakacho, Koganei, Tokyo 184-8588, Japan
E-mail: hrc@cc.tuat.ac.jp
Fax: +81 423 887 044
Tel: +81 423 887 044

b Japan Science and Technology Agency (JST), ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, Japan

Abstract

A stoichiometric reaction of [Ru(η4-2,3-dimethyl-1,3-butadiene)(η4-1,5-COD)(NCMe)] (1a) with diphenylketene at room temperature produces a new zero-valent complex [Ru(η4-4,5-dimethyl-1,1-diphenylhexa-3,5-diene-2-one)(η4-1,5-COD)(NCMe)] (2aa) in 92% yield. This is the first example of conjugated dienyl ketone formation from 1,3-dienes and ketene. Similarly, the treatment of 1a with ethylphenylketene produces the decarbonylated coupling product (Z)-5-alkyl-2,3-dimethyl-5-phenylhepta-1,4-diene (5) in 77% yields.

Graphical abstract: Stoichiometric formation of conjugated dienyl ketones from 1,3-dienes and ketenes at a ruthenium(0) centre

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Article information

DOI
https://doi.org/10.1039/C4NJ01001A
Article type
Paper
Submitted
17 Jun 2014
Accepted
05 Aug 2014
First published
21 Aug 2014

New J. Chem., 2014,38, 5052-5057

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Stoichiometric formation of conjugated dienyl ketones from 1,3-dienes and ketenes at a ruthenium(0) centre

M. Hirano, T. Okamoto, N. Komine and S. Komiya, New J. Chem., 2014, 38, 5052 DOI: 10.1039/C4NJ01001A

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