2007年4月
Pd(OAc)(2)/P((C6H11)-C-c)(3)-Catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- 巻
- 129
- 号
- 14
- 開始ページ
- 4463
- 終了ページ
- 4469
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/ja067372d
- 出版者・発行元
- AMER CHEMICAL SOC
Allylations of aryl halides take place upon treatment of tertiary homoallyl alcohols with aryl halides in the presence of cesium carbonate and a palladium catalyst. The allylation reaction would consist of the following steps: (1) oxidative addition of aryl halide to palladium, (2) ligand exchange between the halide and the homoallyl alcohol affording aryl(homoallyloxy)palladium, (3) retro-allylation of the palladium alkoxide to generate sigma-allyl(aryl)palladium with concomitant liberation of the relevant ketone, and (4) productive reductive elimination. Since the retro-allylation step proceeds in a concerted fashion via a conformationally regulated six-membered cyclic transition state, the allylation reactions are highly regio- and stereospecific when homoallyl alcohols having a substituted allyl group are used. Whereas triarylphosphine is known to serve as a ligand for the palladium-catalyzed allyl transfer reactions, tricyclohexylphosphine proves to significantly expand the scopes of aryl halides to electron-rich aryl chlorides and of homoallyl alcohols to cyclic homoallyl alcohols. The new arylative ring-opening reactions of cyclic homoallyl alcohols allow for the synthesis of ketones having a branched or linear allylarene moiety at the remote terminus in regio- and stereospecific manners.
- リンク情報
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- DOI
- https://doi.org/10.1021/ja067372d
- J-GLOBAL
- https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200902285031224043
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/17373791
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000245723800061&DestApp=WOS_CPL
- URL
- http://orcid.org/0000-0002-0153-1888
- ID情報
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- DOI : 10.1021/ja067372d
- ISSN : 0002-7863
- J-Global ID : 200902285031224043
- ORCIDのPut Code : 27822130
- PubMed ID : 17373791
- Web of Science ID : WOS:000245723800061