Mild uncatalyzed hydroamination of an electrophilic alkyne, ethynylcobalticinium.
نویسندگان
چکیده
Primary and secondary amines react with ethynylcobalticinium under mild conditions in the absence of a catalyst and an additional solvent to give quantitative yields of dark-red microcrystalline cobalticinium trans-enamines that show a remarkable push-pull electronic structure.
منابع مشابه
Unveiling the uncatalyzed reaction of alkynes with 1,2-dipoles for the room temperature synthesis of cyclobutenes.
2-(Pyridinium-1-yl)-1,1-bis(triflyl)ethanides have been used as 1,2-dipole precursors in a metal-free direct [2+2] cycloaddition reaction of alkynes. Starting from stable zwitterionic pyridinium salts, the electron deficient olefin 1,1-bis(trifluoromethylsulfonyl)ethene is generated in situ and immediately reacted at room temperature with an alkyne to afford substituted cyclobutenes. Remarkably...
متن کاملComputational insight into a gold(I) N-heterocyclic carbene mediated alkyne hydroamination reaction.
A gold(I) N-heterocyclic carbene (NHC) complex mediated hydroamination of an alkyne has been modeled using density functional theory (DFT) study. In this regard, alkyne and amine coordination pathways have been investigated for the hydroamination reaction between two representative substrates, namely, MeC≡CH and PhNH(2), catalyzed by a gold(I) NHC based (NHC)AuCl-type precatalyst, namely, [1,3-...
متن کاملPressure-accelerated azide-alkyne cycloaddition: micro capillary versus autoclave reactor performance.
Pressure effects on regioselectivity and yield of cycloaddition reactions have been shown to exist. Nevertheless, high pressure synthetic applications with subsequent benefits in the production of natural products are limited by the general availability of the equipment. In addition, the virtues and limitations of microflow equipment under standard conditions are well established. Herein, we ap...
متن کاملAnomalous ligand effect in gold(I)-catalyzed intramolecular hydroamination of alkynes.
We analyzed the ligand electronic effect in a gold(I)-catalyzed intramolecular alkyne hydroamination, through a DFT and charge-displacement function (CDF) study. We found that, in the presence of π-electron conjugation between the alkyne and the nucleophilic functionality, electron poor ligands modify the coordination mode and the geometric parameters of the substrate in such a way that, contra...
متن کاملDirect access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions
We report a synthetic methodology for the construction of the fused heterocyclic compounds pyrido[2,1-b]quinazolin-9(1H)-ones and pyrrolo[2,1-b]quinazolin-9(1H)-ones through an AgOTf-catalyzed intramolecular alkyne hydroamination reaction. The methodology is applicable to a wide scope of substrates and produces a series of fused quinazolinone heterocycles in good to excellent yields.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 49 52 شماره
صفحات -
تاریخ انتشار 2013