20047-26-1Relevant articles and documents
Transition-Metal-Promoted Alkylations of Unsaturated Alcohols: The Selective Methylation of Homopropargyl Alcohols via Titanium Tetrachloride-Trimethylaluminum
Ewing, James C.,Ferguson, Gregory S.,Moore, Douglas W.,Schultz, Frederick W.,Thompson, David W.
, p. 2124 - 2128 (1985)
The reactions of homopropargyl alcohols with titanium tetrachloride-trimethylaluminum in methylene chloride under mild conditions selectively yield after hydrolysis alkenols of the type HOCH(R)CH2CH=C(R')CH3, R =H, Me, and Et and R'= H, Me, Et, n-Pr, i-Pr, n-C4H9, n-C5H11, and Ph.
Ni-catalyzed stereoselective arylation of inert C-O bonds at low temperatures
Cornella, Josep,Martin, Ruben
supporting information, p. 6298 - 6301 (2014/01/17)
A Ni-catalyzed arylation of inert C-O bonds that operates at temperatures as low as -40 C is described. Unlike other methods for C-O bond cleavage utilizing organometallic species, this protocol operates at low temperatures, thus allowing the presence of sensitive functional groups with exquisite site-selectivity and stereoselectivity.
A Stereoselective Synthesis of Trisubstituted Alkenes. Part 1. Nickel-catalysed Coupling of Grignard Reagents with 5-Alkyl-2,3-dihydrofurans
Kocienski, Philip J.,Pritchard, Martin,Wadman, Sjoerd N.,Whitby, Richard J.,Yeates, Clive L.
, p. 3419 - 3430 (2007/10/02)
5-Alkyl-2,3-dihydrofurans 3a-j prepared by the alkylation of 5-lithio-2,3-dihydrofuran 2 with primary alkyl bromides and iodides, undergo Ni(0)-catalysed coupling with Grignard reagents to give homoallylic alcohols.The yield and stereoselectivity depend on the structure of the Grignard reagent with the best results being obtained with long chain primary Grignard reagents and Grignard reagents lacking β-hydrogens (Me, Ph, Me3SiCH2). 5-(1-Hydroxyalkyl)-2,3-dihydrofurans 20 and 21 are poor substrates for the coupling reaction.Mechanisms are proposed for the coupling as well as competing reduction and isomerisation reactions.
