217947-24-5Relevant articles and documents
Palladium-catalyzed electrophilic substitution of allyl chlorides and acetates via bis-allylpalladium intermediates
Wallner, Olov A.,Szabo, Kalman J.
, p. 2934 - 2943 (2003)
Palladium-catalyzed electrophilic allylic substitution of functionalized allyl chlorides and allyl acetates can be achieved in the presence of hexamethylditin under mild and neutral reaction conditions. This efficient one-pot procedure involves palladium-catalyzed formation of transient allylstannanes followed by generation of a bis-allylpalladium intermediate, which subsequently reacts with electrophiles. Using this catalytic transformation, various aldehydes and imines can be allylated providing highly functionalized homoallyl alcohols and amines. Furthermore, tandem bis-allylation reactions could be performed by employing tosyl isocyanate and benzylidenemalonitrile as substrates. A particularly interesting mechanistic feature of this reaction is that palladium catalyzes up to three different transformations in each catalytic cycle. Various allylic functionalities, including COOEt, CONH2, COCH3, CN, Ph, and CH3, are tolerated in the catalytic reactions due to the application of neutral and mild reaction conditions. The substitution reaction occurs with very high regioselectivity at the branched allylic terminus. Moreover, in several reactions, a high stereoselectivity was observed indicating that this new catalytic process has a high potential for stereoselective synthesis. The regioselectivity of the reaction can be explained on the basis of DFT calculations. These studies indicate that the allylic substituent prefers the γ-position of the η1-allyl moiety of the reaction intermediate.
A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
Yin, JieXiang,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2347 - 2354 (2020/02/04)
A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re
Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
Fan, Xiaohui,Zhu, Hong-Bo,Lv, Hao,Guo, Kun,Guan, Yong-Hong,Cui, Xiao-Meng,An, Bin,Pu, Yan-Ling
, p. 588 - 592 (2015/09/01)
An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.
PCN- and PCS-pincer palladium complexes as tandem catalysts in homoallylation reactions
Li, Jie,Siegler, Maxime,Lutz, Martin,Spek, Anthony L.,Klein Gebbink, Robertus J. M.,Van Koten, Gerard
experimental part, p. 2474 - 2488 (2010/12/25)
Novel PCN- and PCS-pincer palladium complexes 2-(dimethylamino)methyl-5- methoxy-6-(diphenylphosphinoxy)phenylpalladium(II) bromide (1), 2-(phenylimino)-5-methoxy-6-(diphenylphosphinoxy)phenylpalladium(II) bromide (2), 2-(phenylthiomethyl)-5-methoxy-6-(di
