Rhodium(I)- or Palladium(II)-Catalyzed 1,4-Additions of Organoboron, -silicon and -bismuth Compounds to Electron-deficient Alkenes
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- Yamamoto Yasunori
- Graduate School of Engineering, Hokkaido University
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- Nishikata Takashi
- Japan Science and Technology Agency
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- Miyaura Norio
- Graduate School of Engineering, Hokkaido University
書誌事項
- タイトル別名
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- Rhodium 1 or Palladium 2 Catalyzed 1 4 Additions of Organoboron silicon and bismuth Compounds to Electron deficient Alkenes
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An enantioselective synthesis of cyclic and acyclic β-aryl ketones and esters via palladium (II) - or rhodium (I) -catalyzed 1, 4-addition of Ar- [m] (m=B(OH)2, BF3K, Si(OMe)3, SiF3, BiAr2) to α, β-unsaturated ketones or esters is described. The catalytic cycle involves transmetalation between Ar- [M] and palladium (II) or rhodium (I) complexes as the key process, the mechanism of which is discussed on the basis of characterization of the transmetalation intermediate and electronic effect of the substituents. The enantioselection mechanism and efficiency of a chiraphos ligand for structurally planar α, β-unsaturated ketones are discussed on the basis of the X-ray structure of the catalyst and results of DFT computational studies on the modes of coordination of the substrates to the phenylrhodium (I) / (S, S) -chiraphos intermediate.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 64 (11), 1112-1121, 2006
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680287966592
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- NII論文ID
- 10020608620
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BD28Xht1Wks7bM
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 8573762
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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- 使用不可