- Rh-catalyzed 1,4-addition of triallyl(aryl)silanes to α,β-unsaturated carbonyl compounds
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Rh-catalyzed 1,4-addition of triallyl(aryl)silane to α,β-unsaturated carbonyl compounds was developed. Triallyl(aryl)silanes were used as air- and moisture-stable silicon nucleophiles. Allylsilanes were converted to silanols in situ and underwent transmetalation. This method can accept a wide range of functionalized triallyl(aryl)silane and α,β-unsaturated carbonyl compounds.
- Kamei, Toshiyuki,Uryu, Mizuho,Shimada, Toyoshi
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supporting information
p. 1622 - 1624
(2018/03/22)
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- Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts
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Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.
- Wu, Chunlin,Yue, Guizhou,Nielsen, Christian Duc-Trieu,Xu, Kai,Hirao, Hajime,Zhou, Jianrong
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supporting information
p. 742 - 745
(2016/02/05)
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- Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes
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The addition of aryltrialkoxysilanes to α,β-unsaturated carbonyl compounds (ketones, aldehydes) and nitroalkenes in the presence of SbCl3, TBAF, AcOH, and a catalytic amount of Pd(OAc)2, in CH3CN at 60 °C, provides the corresponding conjugate addition products in moderate to good yields. The addition of equimolar amounts of SbCl3 and TBAF is necessary for this reaction to proceed smoothly. The arylpalladium complex, which is generated by the transmetalation from a putative hypercoordinate silicon compound, is considered to be the catalytically active species.
- Denmark, Scott E.,Amishiro, Nobuyoshi
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p. 6997 - 7003
(2007/10/03)
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- New Synthetic Methods. Conjugate Addition of Alkyl Groups to Electron Deficient Olefins with Nitroalkanes as Alkyl Anion Equivalents
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The sequence of the Michael addition of nitroalkanes and denitration from the adduct provides a new and general method for conjugate addition of primary and secondary alkyl groups to electron deficient olefins such as α,β-unsaturated aldehydes, ketones, esters, nitriles, sulfoxides, and sulfones.
- Ono, Noboru,Kamimura, Akio,Miyake, Hideyoshi,Hamamoto, Isami,Kaji, Aritsune
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p. 3692 - 3698
(2007/10/02)
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