89787-29-1Relevant academic research and scientific papers
Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source
Chen, Chen,Huang, Yujie,Ding, Jie,Liu, Liying,Zhu, Bolin
supporting information, p. 794 - 801 (2022/01/04)
We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.
Tosylhydrazide-promoted palladium-catalyzed reaction of β-aminoketones with o-dihaloarenes: Combining organocatalysis and transition-metal catalysis
Barluenga, Jose,Quinones, Noelia,Cabal, Maria-Paz,Aznar, Fernando,Valdes, Carlos
supporting information; experimental part, p. 2350 - 2353 (2011/04/21)
(Chemical Equation Presented) Working in tandem: Mannich adducts obtained by organocatalyzed processes are readily transformed into phenanthridine and quinoline derivatives by a Pd-catalyzed cascade reaction involving tosylhydrazide (TsNHNH2)-promoted cross-coupling followed by intramolecular amination (see scheme; MW=microwave). The enantioselectivity achieved in the organocatalytic reaction is maintained throughout the process.
Electrochemical oxidation of 4-substituted N,N-dimethylaniline in the presence of silyl enol ether. Effect of the substituent on the formation of Mannich bases. II.
Renaud, Roger N.,Stephens, Campbell J.,Brochu, Gaetan
, p. 565 - 569 (2007/10/02)
The formation of Mannich bases from the electrochemical oxidation of 4-substituted N,N-dimethylaniline in the presence of silyl enol ether was studied.The yield of bases obtained depended on the relative oxidation potentials of the starting amine compound and the base formed.An electron-donating substituent on the amine showed a large difference in the oxidation potentials and gave the highest yield of product.On the other hand, the oxidation potentials were very close with an electron-withdrawing substituent and the yield in base was relatively much lower.Furthermore, the main product in the case of an electron-withdrawing group in the presence of 1-trimethylsilyloxy-1-cyclohexene was 4-substituted 2-(2-oxocyclohexyl)-N,N-dimethylaniline.Some side products were also isolated and were identified as N,N-diketonic compounds.
