101441-87-6Relevant articles and documents
Tert-Butoxide-Mediated Arylation of 2-Substituted Cyanoacetates with Diaryliodonium Salts
Qian, Xiaofei,Han, Jianwei,Wang, Limin
, p. 940 - 946 (2016/04/05)
A transition metal-free direct arylation of 2-substituted cyanoacetates with diaryliodonium salts was developed. With this approach, a wide range of α-tolunitrile derivatives has been synthesized in good to excellent yields of 45-92%. Furthermore, the practicability of this approach is further manifested in the synthesis of a related bioactive agent of glutarimide.
Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands
Beare, Neil A.,Hartwig, John F.
, p. 541 - 555 (2007/10/03)
Palladium-catalyzed reactions of aryl bromides and chlorides with two common stabilized carbanions - enolates of dialkyl malonates and alkyl cyanoesters - are reported. An exploration of the scope of these reactions was conducted, and the processes were shown to occur in a general fashion. Using P(t-Bu)3 (1), the pentaphenylferrocenyl ligand (Ph5C5)Fe(C5H4)P(t-Bu) 2 (2), or the adamantyl ligand (1-Ad)P(t-Bu)2 (3), reactions of electron-poor and electron-rich, sterically hindered and unhindered aryl bromides and chlorides were shown to react with diethyl malonate, di-tertbutyl malonate, diethyl fluoromalonate, ethyl cyanoacetate, and ethyl phenylcyanoacetate. Although alkyl malonates and ethyl alkylcyanoacetates did not react with aryl halides using these catalysts, the same products were formed conveniently in one pot from diethylmalonate by cross-coupling of an aryl halide in the presence of excess base and subsequent alkylation.
