60896-02-8

Upstream product

• 76346-98-0 (Z)-(1-iodo-1-hexenyl)trimethylsilane 
• 66270-63-1 [(1E)-1-iodo-hex-1-enyl]-trimethyl-silane 
• 591-50-4 iodobenzene 
• 338999-00-1 dicyclohexyl[(Z)-1-(trimethylsilyl)hex-1-enyl]borane 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 
• 683771-98-4 (E)-1-trimethylsilyl-1-phenyltelluro-1-hexene 
• 124582-31-6 (E)-1-trimethylsilyl-1-tributylstannyl-1-hexene 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

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

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.

Pd-catalyzed regio- and stereoselective addition of boronic acids to silylacetylenes: A stereodivergent assembly of β,β-disubstituted alkenylsilanes and alkenyl halides

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.

A facile stereoselective synthesis of (E)-α-silylvinylstannanes via hydromagnesiation of alkynylsilanes

(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.

Stereoselective synthesis of (E)-α-silylvinyl tellurides via the hydrozirconation reaction of alkynylsilanes

(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.

Stereoselective synthesis of (E)-α-aryltellurenylvinylsilanes via hydromagnesiation reaction of alkynylsilanes

(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

Alkynylsilanes as convenient precursors for the stereoselective synthesis of (E)-disubstituted alkenes

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.

TRANSITION METAL ?-COMPLEXES IN ORGANIC SYNTHESIS 5. CROSS-COUPLING OF ORGANOMANGANESE COMPOUNDS WITH ALKENYL IODIDES

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.