2001年1月
A novel reductive dimerization/oxidative dehydrogenation of aldimines mediated by lanthanoid metals
JOURNAL OF ORGANIC CHEMISTRY
- ,
- ,
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- 巻
- 66
- 号
- 2
- 開始ページ
- 514
- 終了ページ
- 520
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jo001328d
- 出版者・発行元
- AMER CHEMICAL SOC
A lanthanoid metal-mediated novel reductive dimerization/oxidative dehydrogenation of a variety of aldimines has been achieved. Aromatic aldimines (1) were dimerized in the presence of 0.5 mol of ytterbium metal (Yb) and 1-naphthaldehyde (1-NpCHO) to give the corresponding vicinal diimines (2) in good to high yields. Samarium metal (Sm) or samarium(II) diiodide (SmI2) gives unsatisfied yields under the same reaction conditions. As an oxidant, 1-NpCHO gives the best result. In addition, HMPA plays an important role as a cosolvent in this reaction. Reaction of various aldimines with Yb metal is disscussed in detail. Moreover, it has been found that the electron-donating substitutents on the benzene ring promote the reaction and that the electron-withdrawing substitutents retard the reaction. The reaction of deuterated N-benzylideneaniline with Yb metal confirmed that transformation of the hydride occurred from aldimines to the oxidant aldehyde. The mechanism of the reaction was discussed.
- リンク情報
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- DOI
- https://doi.org/10.1021/jo001328d
- CiNii Articles
- http://ci.nii.ac.jp/naid/80012263056
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/11429823
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000166560600023&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/jo001328d
- ISSN : 0022-3263
- CiNii Articles ID : 80012263056
- PubMed ID : 11429823
- Web of Science ID : WOS:000166560600023