93321-44-9Relevant articles and documents
Indium tribromide-catalyzed deacetoxylation of propargylic acetate with triethylsilane
Sakai, Norio,Hirasawa, Maki,Konakahara, Takeo
, p. 6407 - 6409 (2005)
Indium(III) bromide catalyzed the deacetoxylation of propargylic acetates with Et3SiH to produce the corresponding internal alkynes containing a variety of functional groups in good yields.
Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst
Shao, Xue Bei,Zhang, Zhen,Li, Qing Han,Zhao, Zhi Gang
, p. 4797 - 4806 (2018/07/13)
A highly efficient and simple route for the synthesis of multi-substituted allenes has been developed by a nickel catalyzed SN2′ substitution reaction of propargyl esters with organic aluminium reagents under mild conditions, which gave the corresponding multi-substituted allenes in good to excellent yields (up to 92%) and high selectivities (up to 99%) at 60 °C for 6 h in THF. Aryls bearing electron-donating or electron-withdrawing groups in propargyl esters gave products in good yields. In addition, the multi-substituted allenes bearing a thienyl or a pyridyl group were obtained in 95-97% selectivities with isolated yields of 72-83%. Furthermore, the SN2′ substitution reaction worked efficiently with propargyl carbonate compounds as well. On the basis of the experimental results, a possible catalytic cycle has been proposed.
Palladium-catalyzed, ligand-free SN2’ substitution reactions of organoaluminum with propargyl acetates for the synthesis of multi-substituted allenes
Shao, Xuebei,Wen, Chang,Zhang, Gang,Cao, Kangping,Wu, Ling,Li, Qinghan
, p. 68 - 75 (2018/06/29)
We describe a convenient method for the synthesis of multi-substituted allenes from SN2′ substitution reactions organoaluminum with propargyl acetates: The SN2′ substitution reaction of organoaluminum (0.4 mmol) with propargyl acetat
