- Copper(I)-catalyzed transfer of 1-(trimethylsilyl)-1-alkenyl group from boron to tin: Regio- and stereoselective synthesis of (E)-1-(tributylstannyl)-1-(trimethylsilyl)-1-alkenes
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Stereoselective transfer of 1-(trimethylsilyl)-1-alkenyl group from boron to tin has been realized by a catalytic amount of copper(I) iodide in the presence of aqueous NaOH under extremely mild reaction conditions to provide (E)-1-(tributylstannyl)-1-(trimethylsilyl)-1-alkenes (2) exclusively in good to high yields.
- Hoshi,Shirakawa,Takeda
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- Pd-catalyzed regio- and stereoselective addition of boronic acids to silylacetylenes: A stereodivergent assembly of β,β-disubstituted alkenylsilanes and alkenyl halides
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An efficient Pd-catalyzed addition of boronic acids to silylacetylenes is described, providing β,β-disubstituted (E)- or (Z)-alkenylsilanes in satisfactory yields with excellent regio- and stereoselectivity under mild reaction conditions. It represents the first highly regio- and stereoselective addition of boronic acids to aryl and alkenyl silylacetylenes. Moreover, the sequential Pd-catalyzed boron addition/N-halosuccinimide-mediated halodesilylation reaction results in a stereodivergent approach to β,β-disubstituted alkenyl halides, which can serve as versatile synthetic intermediates for the stereodivergent assembly of (E)- and (Z)-trisubstituted alkenes via transition-metal-catalyzed cross-coupling reactions.
- Kong, Wei,Che, Chao,Wu, Jialin,Ma, Liai,Zhu, Gangguo
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p. 5799 - 5805
(2014/07/08)
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- Stereoselective synthesis of (E)-α-silylvinyl tellurides via the hydrozirconation reaction of alkynylsilanes
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(E)-α-silylvinyl tellurides have been synthesised stereoselectively via the hydrozirconation of alkynylsilanes, followed by reaction with aryltellurenyl iodides. (E)-α-Silylvinyl tellurides can undergo cross coupling reaction with Grignard reagents in the presence of [NiCl 2(PPh3)2] catalyst to give (Z)-1,2-disubstituted vinylsilanes in good yields.
- Cai, Mingzhong,Huang, Jiadi
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p. 228 - 229
(2007/10/03)
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- A facile stereoselective synthesis of (E)-α-silylvinylstannanes via hydromagnesiation of alkynylsilanes
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(E)-α-Silylvinylstannanes have been synthesized by the hydromagnesiation reaction of alkynylsilanes, followed by the reaction with trialkylstannyl chlorides. (E)-α-Silylvinylstannanes can undergo the cross-coupling reaction with aryl iodides in the presence of a catalytic amounts of Pd(PPh3)4 and CuI to afford (Z)-1,2-disubstituted vinylsilanes in good yields.
- Cai, Mingzhong,Hao, Wenyan,Zhao, Hong,Xia, Jun
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p. 3593 - 3597
(2007/10/03)
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- Stereoselective synthesis of (E)-α-aryltellurenylvinylsilanes via hydromagnesiation reaction of alkynylsilanes
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(E)-α-Aryltellurenylvinylsilanes have been synthesized stereoselectively via the hydromagnesiation of alkynylsilanes, followed by the reaction with aryltellurenyl iodides. (E)-α-Aryltellurenylvinylsilanes can undergo the cross coupling reaction with Grign
- Cai, Mingzhong,Hao, Wenyan,Zhao, Hong,Xia, Jun
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p. 1714 - 1717
(2007/10/03)
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- Alkynylsilanes as convenient precursors for the stereoselective synthesis of (E)-disubstituted alkenes
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Hydromagnesiation of alkynylsilanes 1 gives (Z)-α-silylvinyl Grignard reagents 2, which are reacted with alkyl iodides or aryl iodides in the presence of Cul or Pd(PPh3)4 catalysts to afford (Z)-1,2-disubstituted vinylsilanes 3 in good yields. Intermediates 3 can undergo a desilylation reaction to give (E)-disubstituted alkenes 4 in high yields.
- Zhao, Hong,Cai, Mingzhong
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p. 608 - 610
(2007/10/03)
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- TRANSITION METAL ?-COMPLEXES IN ORGANIC SYNTHESIS 5. CROSS-COUPLING OF ORGANOMANGANESE COMPOUNDS WITH ALKENYL IODIDES
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Aryl organomanganese compounds ArMnX and Ph3MnLi (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-BrC6H4, α-naphthyl; X = Cl, Br) react with alkenyl iodides RR1C=CR2I (R = H, Pr, Bu, i-Bu, C6H13, CH2=CHCH2, Ph; R1 = H, Pr, C5H11; R2 = H, Pr, SiMe3) in THF at 0-20 deg C to give cross-coupling products RR1C=CR2Ar in high yields.
- Kasatkin, A. N.,Romanova, T. Yu.,Tsypyshev, O. Yu.,Tolstikov, G. A.,Lomakina, S. I.
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p. 2410 - 2415
(2007/10/02)
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