Reaction of diazonium salts with transition metals. Part 11. Palladium-catalyzed aryldesilylation of alkenylsilanes by arenediazonium salts
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1959-1964
- https://doi.org/10.1039/p19860001959
Abstract
Under palladium(0) catalysis, both (E)- and (Z)-RCHCHSiMe3(RRh, 4-MeC6H4, 4-NO2C6H4, n-C6H13, and MeOCH2) were easily aryldesilylated by ArN2X (ArPh, 4-MeC6H4, 4-BrC6H4 and 4-NO2C6H4; XBF4, PF6, and Cl) to give (E)-RCHCHAr and RC(Ar)CH2 as the main products at 25 °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)-RCHCHSiMe3, respectively, are proposed for the formation of (E)-RCHCHAr from either isomer of RCHCHSiMe3.Keywords
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