88262-01-5Relevant academic research and scientific papers
Reaction of Diazonium Salts with Transition Metals. Part 11. Palladium-catalyzed Aryldesilylation of Alkenylsilanes by Arenediazonium Salts
Ikenaga, Kazutoshi,Kikukawa, Kiyoshi,Matsuda, Tsutomu
, p. 1959 - 1964 (2007/10/02)
Under palladium(0) catalysis, both (E)- and (Z)-RCH=CHSiMe3(R=Rh, 4-MeC6H4, 4-NO2C6H4, n-C6H13, and MeOCH2) were easily aryldesilylated by ArN2X(Ar=Ph, 4-MeC6H4, 4-BrC6H4 and 4-NO2C6H4; X=BF4, PF6, and Cl) to give (E)-RCH=CHAr and RC(Ar)=CH2 as the main products at 25 deg C in acetonitrile. anti- and syn-1,2-Elimination of Pd(0) and Me3Si from the adducts, threo- and erythro-RCH(PdX)CHSiMe3, generated from ArPdX and (E) and (Z)-RCH=CHSiMe3, respectively, are proposed for the formation of (E)-RCH=CHAr from either isomer of RCH=CHSiMe3.
FORMATION OF α-SILYLVINYLLITHIUM REAGENTS: REACTIONS OF α-SILYL- AND α-STANNYL-VINYLLITHIUMS WITH ALDEHYDES AND KETONES
Mitchell, Terence N.,Reimann, Werner
, p. 163 - 172 (2007/10/02)
The formation of α-trimethylsilylvinyllithium compounds from 1-trimethylsilyl-1-trimethylstannyl-1-alkenes have been studied and their stabilities investigated. α-Trimethylsilyl- and α-trimethylstannyl-vinyllithiums undergo 1,2-addition to aldehydes and non-enolisable ketones, to give silyl- or stannyl-substituted allylic alcohols; α,β-unsaturated ketones, however, undergo 1,4-addition to give homoallylic ketones.
STEREOCHEMISTRY OF REACTION OF (E)- AND (Z)-Β-TRIMETHYLSILYLSTYRENE WITH ARYLPALLADIUM TETRAFLUOROBORATES GENERATED FROM ARENEDIAZONIUM TETRAFLUOROBORATES AND PALLADIUM(0)
Kikukawa, Kiyoshi,Ikenaga, Kazutoshi,Wada, Fumio,Matsuda, Tsutomu
, p. 1337 - 1340 (2007/10/02)
(E)- and (Z)-PhCH=CHSiMe3 react easily with +BF4- to give (E)-PhCH=CHAr and Ph(Ar)C=CH2 at 25 deg C.Stereochemistry of the desilylation is disclosed by using (E)- and (Z)-PhCH=CDSiMe3, that is syn-addition of Ar-Pd species followed by anti-elimination of Pd and Me3Si moiety for (E)-isomer and syn-elimination for (Z)-isomer are proposed.
