76006-58-1Relevant academic research and scientific papers
Palladium-catalyzed carbonylation of allylamines via C-N bond activation leading to β,γ-unsaturated amides
Yu, Hui,Zhang, Guoying,Liu, Zong-Jian,Huang, Hanmin
, p. 64235 - 64237 (2015/02/19)
Pd(Xantphos)Cl2 has been identified as an efficient catalyst for the direct carbonylation of allylamines via C-N bond activation. The reaction proceeds smoothly and provides β,γ-unsaturated amides in good to excellent yields under relatively mi
Ruthenium Complex-Catalyzed Carbonylation of Allylic Compounds
Mitsudo, Take-aki,Suzuki, Nobuyoshi,Kondo, Teruyuki,Watanabe, Yoshihisa
, p. 7759 - 7765 (2007/10/02)
Allylic alkyl carbonates are carbonylated under 40 atm of carbon monoxide at 100-120 deg C in the presence of a catalytic amount of Ru3(CO)12/1,10-phenanthroline to give α,β- or β,γ-unsaturated esters in good to high yields.For example, cinnamyl methyl carbonate afforded the corresponding β,γ-unsaturated esters, methyl trans-4-phenyl-3-butenoate (1) in 93percent yield.The regioselectivity in the carbonylation of crotyl methyl carbonate is unusual and it depends on the carbon monoxide pressure.The more sterically hindered carbon (γ-carbon) is predominantly carbonylated at 20-50 atm.When the reaction of cinnamyl methyl carbonate was performed at elevated temperature (150 deg C) without 1,10-phenanthroline, the dimer of 1, dimethyl 3-benzyl-2-(trans-2-phenylvinyl)glutarate, was obtained in 56percent yield.In the presence of secondary amines, allylic alkyl carbonates were carbonylated mainly at α-carbon to give α,β- or β,γ-unsaturated amides in high yields.
