256663-37-3Relevant articles and documents
Palladium-Catalyzed Regiocontrollable Reductive Heck Reaction of Unactivated Aliphatic Alkenes
Wang, Chengdong,Xiao, Guanlin,Guo, Tao,Ding, Yalan,Wu, Xiaojin,Loh, Teck-Peng
supporting information, p. 9332 - 9336 (2018/06/29)
A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been first developed. This method affords γ- and δ-arylated alkyl carboxylic acid derivatives in high yields with complete anti-Markovnikov selectivity. Notably, the coupling process is stereoretentive for the alkyl chain. Mechanistically, alkyl palladacycle intermediates stabilized by directing group and ligand, hydride species multigenerated from PS/TFA reductant, are two key factors that successfully promote the reaction and regioselectivity.
Indium-mediated Reformatsky-Claisen rearrangement
Ishihara, Jun,Watanabe, Yuki,Koyama, Noriko,Nishino, Yukihiro,Takahashi, Keisuke,Hatakeyama, Susumi
experimental part, p. 3659 - 3667 (2011/06/21)
A new variant of the Reformatsky-Claisen rearrangement is described. The reaction of substituted allyl α-bromoacetates with indium and indium(III) chloride under ultrasonication provides a general entry into the functionalized synthon.
Transition-metal catalyzed synthesis of δ-hydroxy-γ-lactones from bis(trimethylsilyl) ketene acetals and allylic acetates via γ-unsaturated carboxylic acids. Comments on the formation of α-cyclopropyl carboxylic acids
Rudler, Henri,Harris, Paul,Parlier, Andrée,Cantagrel, Frédéric,Denise, Bernard,Bellassoued, Moncef,Vaissermann, Jacqueline
, p. 186 - 202 (2007/10/03)
Bis(trimethylsilyl)ketene acetals react with allylic acetates in the presence of Pd(0) complexes to give γ-unsaturated carboxylic acids together with α-cyclopropyl carboxylic acids. The unsaturated acids can be converted catalytically to δ-hydroxy-yγ-lactones by the H2O2/MTO system (methyltrioxorhenium) and to butenolides by Pd(II) catalyzed intramolecular cyclization reactions. The structure of two of these lactones has been established by X-ray analysis. The mechanism of the formation of the cyclopropanic acids will be discussed.