874338-64-4Relevant academic research and scientific papers
Neighboring Carbonyl Group Assisted Hydration of Unsymmetrical Aryl Alkynes Overriding Regular Selectivity
Mendhekar, Kishor L.,Pradhan, Tapas R.,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.
, p. 5787 - 5797 (2019/08/21)
A mild and highly regioselective gold-catalyzed hydration of γ-acetoxy aryl alkynes leading to anti-Markovnikov products by the assistance of a neighboring carbonyl group is presented. The reaction procedure operates under room temperature conditions with
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.
Highly efficient synthesis of allenes from trimethylaluminum reagent and propargyl acetates mediated by a palladium catalyst
Li, Qing-Han,Jeng, Jung-Yuan,Gau, Han-Mou
, p. 7916 - 7923 (2015/02/02)
A series of propargyl acetates were prepared and used as propargyl electrophiles for coupling reactions with trimethylaluminum. The simple catalytic system of palladium(II) acetate (1 mol-%) and tri(o-tolyl)phosphine (2 mol-%) worked efficiently for a wide variety of aromatic and aliphatic propargyl acetates, producing the substituted allenes in good to excellent yields of up to 94% in tetrahydrofuran. The process was simple and easily performed, and it provides an efficient method for the synthesis of substituted allene derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.
Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes
Zhang, Xiaoxia,Sarkar, Sampa,Larock, Richard C.
, p. 236 - 243 (2007/10/03)
A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by IC1, I 2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.
