- Synthesis of Silaphenalenes by Ruthenium-Catalyzed Annulation between 1-Naphthylsilanes and Internal Alkynes through C-H Bond Cleavage
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Ruthenium-catalyzed annulation of 1-naphthylsilanes with internal alkynes afforded silaphenalenes through cleavage of the C-H bond at the 8-position of the naphthalene. [RuH2(CO){P(p-FC6H4)3}3] efficiently catalyzed the reaction. The use of 1-naphthyldiphenylsilane as a substrate resulted in a better yield of the annulation product compared to the use of silanes with alkyl groups on the silicon atom. Internal alkynes with both aryl and alkyl groups were tolerated in this reaction. Annulation rather than hydrosilylation: A ruthenium catalyst favored annulation products rather than hydrosilylation products in the reaction of 1-naphthylsilanes and alkynes. The annulation proceeded with selective cleavage of the C-H bond at the 8-position of naphthalene. Substrate scope revealed that substituents on the silicon atom played a crucial role and the phenyl group helped to increase the yields.
- Tokoro, Yuichiro,Sugita, Kengo,Fukuzawa, Shin-Ichi
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supporting information
p. 13229 - 13232
(2015/09/15)
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- Integrated palladium-catalyzed arylation of heavier groupa 14 hydrides
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A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base. The reaction conditions can be applied to the cross-coupling of tertiary, secondary, and primary Groupa 14 compounds. In most cases, the desired arylated products were obtained in synthetically useful yields. Even in the case of aryl iodides containing OH, NH2, CN, or CO2R groups, the reactions proceeded with good to high yields with tolerance of these reactive functional groups. A possible application of this method is the unique synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-ylmethyl)silane derivative. A convenient procedure has been developed for the preparation of Groupa 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Groupa 14 hydrides in the presence of a base (see picture). Application of this method in the synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-yl-methyl)silane derivative is demonstrated. Copyright
- Lesbani, Aldes,Kondo, Hitoshi,Yabusaki, Yusuke,Nakai, Misaki,Yamanoi, Yoshinori,Nishihara, Hiroshi
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supporting information; experimental part
p. 13519 - 13527
(2011/02/24)
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- Selective synthesis of monohydrosilanes by the reactions of organoytterbium iodides with dihydrosilanes
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Monohydrosilanes can be prepared selectively in high yields from the reaction of various aryl and alkyl iodides with ytterbium metal followed by the reaction with dihydrosilanes.
- Jin, Wu-Song,Makioka, Yoshikazu,Kitamura, Tsugio,Fujiwara, Yuzo
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p. 955 - 956
(2007/10/03)
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- Reaction of silyl(carbonyl)iron complexes with liAlH4 giving methylsilanes: Reduction of a carbonyl ligand and coupling with a silyl group
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Treatment of CpFe(CO)2SiR3 (R3 = (pTol)2H, (pTol)2Me, MePh(1-Nap); 1-Nap = 1-naphthyl) with LiAlH4 in ether or THF at room temperature gave CH3SiR3 as a major product in moderate to high yield. The labeling experiments using LiAlD4 and CpFe(13CO)2SiR(pTol)2 (R = H, Me) proved unambiguously that the carbonyl ligand is reduced with LiAlH4 and coupled with the silyl group to give the methylsilanc.
- Tobita, Hiromi,Shiozawa, Rie,Ogino, Hiroshi
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p. 805 - 806
(2007/10/03)
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- METHYLPHENYLTRIPHENYLGERMYLSILANES FONCTIONNELS OPTIQUEMENT ACTIFS
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The structure of the unsymmetric compound MePh(X)SiGePh3 (X=H, F, Cl, OR) has been resolved.The stereochemistry of nucleophilic substitutions at silicon is not changed with Ph3Ge as substituent.Stereochemical correlations allow the determination of absolute configurations.
- Corriu, R. J. P.,Ould-Kada, S.,Lanneau, G.
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- CLEAVAGE OF SILICON- AND GERMANIUM-TRANSITION METAL BONDS. DEPENDENCE OF THE STEREOCHEMISTRY ON THE NATURE OF THE LIGANDS AND THE GEOMETRY OF COMPLEXES
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The cleavages of some new optically active complexes containing Co-Si (or -Ge), Mn-Si (or -Ge), Re-Ge and W-Ge bonds are described.Electrophiles cleave the Co-Si bond with good retention of configuration at silicon, while the Mn-Si bond is not cleaved und
- Cerveau, Genevieve,Colomer, Ernesto,Corriu, Robert J. P.
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- THE REARRANGEMENT OF 1-NAPHTHYLPHENYLMETHYLSILANE
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1-Naphthylphenylmethylsilane has been shown to undergo rearrangement to the 2-isomer when treated with HI in benzene or ether-benzene; protodesilylation also occurs.The rearrangement also takes place when 1-naphthylphenylmethylsilane is heated at 210-220 deg C.
- Becker, Barbara,Herman, Aleksander,Wojnowski, Wieslaw
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p. 293 - 298
(2007/10/02)
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