78999-89-0Relevant academic research and scientific papers
Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water
Wang, Rui,Ma, Mengyue,Gong, Xu,Panetti, Grace B.,Fan, Xinyuan,Walsh, Patrick J.
supporting information, p. 2433 - 2436 (2018/04/27)
A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.
Access to α-Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide
Guo, Chun-Xiao,Zhang, Wen-Zhen,Zhou, Hui,Zhang, Ning,Lu, Xiao-Bing
supporting information, p. 17156 - 17159 (2016/11/23)
A straightforward and transition-metal-free approach for the efficient synthesis of α-arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.
Aroylation of Carbanions Derived from N-(Diphenylmethyl)arylmethanimines. A Synthesis of 4-Aroyloxy-2-azabuta-1,3-dienes
Armesto, Diego,Ortiz, Maria J.,Perez-Ossorio, Rafael
, p. 2021 - 2026 (2007/10/02)
The acylation of carbanions derived from N-(diphenylmethyl)arylmethanimines using aroyl chlorides, allows the preparation of a new type of substituted 2-azabuta-1,3-dienes in which the imino group is conjugated with an enol ester.The reaction is quite general and facilitates the preparation of a wide range of 2-azadienes with electron-donating and electron-withdrawing groups on the phenyl rings.The site selectivity for the attack of the electrophile on the aza-allyl anion can be controlled by the substituents on the carbanion and on the hardness of the electrophile.
Aroylation of n-alkylmethanimines. A synthesis of novel substituted 2-aza-buta-1,3-dienes.
Armesto, Diego,Ortiz, Maria J.,Perez-Ossorio, Rafael
, p. 2203 - 2206 (2007/10/02)
The aroylation of carbanions derived from N-benzyl-diphenylmethanimine and N-(diphenylmethyl )-arylmethanimines yields highly substituted 2-aza-buta- 1,3-dienes in which the imino group is conjugated with an enol ester. A similar reaction with N-(diphenyl
