Efficient iron(III)-catalyzed three-component coupling reaction of alkynes, CH2Cl2 and amines to propargylamines.
نویسندگان
چکیده
An iron(III)-catalyzed three-component coupling reaction of alkynes, CH(2)Cl(2) and amines was developed for facile synthesis of propargylamines. Preliminary mechanism investigation using in situ FT-IR reveals that the crucial Fe-acetylide intermediate could be formed through C-H bond activation of alkynes thanks to cooperative effect of FeCl(3) and 1,1,3,3-tetramethylguanidine.
منابع مشابه
Preparation of Ag2S Nanoparticles and using as Catalyst for the A3-coupling (Aldehyde-Amine-Alkyne) Reaction
Microwave assisted facile one-step approach was adopted to prepare mono-dispersed silver sulfide nanoparticles. The structures of the synthesized Ag2S nanoparticles were confirmed by Fourier-transform infrared spectroscopy (FT-IR), diffuse reflectance UV-vis spectroscopy (DRS), X-ray diffractometer (XRD), energy dispersive X-ray analysis (EDX) and transmission electron microscope (TEM). The pre...
متن کاملChemoselective C-H bond activation: ligand and solvent free iron-catalyzed oxidative C-C cross-coupling of tertiary amines with terminal alkynes. Reaction scope and mechanism.
FeCl(2) catalyzes the oxidative C-C cross-coupling of tertiary amines with terminal alkynes into propargylamines using (t-BuO)(2) as oxidant. The reaction can be applied to aromatic and aliphatic amines and alkynes without solvent. High chemoselectivity for aminomethyl groups is due to a steric factor.
متن کاملMechanistic insights into the one-pot synthesis of propargylamines from terminal alkynes and amines in chlorinated solvents catalyzed by gold compounds and nanoparticles.
Propargylamines can be obtained from secondary amines and terminal alkynes in chlorinated solvents by a three- and two-component synthesis catalyzed by gold compounds and nanoparticles (Au-NP) under mild conditions. The use of dichloromethane allows for the activation of two C-Cl bonds and a clean transfer of the methylene fragment to the final product. The scope of the reaction as well as the ...
متن کاملGreen and efficient synthesis of propargylamines via A3 coupling reaction using a copper (II)–thioamide combination
A one pot green three‐component coupling reaction of aldehyde, phenylacetylene, and amine derivatives in the presence of copper (II)–thioamide combination as a novel and efficient heterogeneous catalyst under solvent–free conditions is reported. The catalyst displayed high activity and afforded the corresponding propargylamines in good to high yields. The key to this procedure was the generatio...
متن کاملAu3+/Au0 Supported on Chromium(III) Terephthalate Metal Organic Framework (MIL-101) as an Efficient Heterogeneous Catalystfor Three-Component Coupling Synthesis of Propargylamines
Post-synthesis modification is a useful method for the functionalization of metal-organic frameworks (MOFs). A novel catalyst Au@MIL-101-ED-SA (ED = ethylenediamine, SA = salicylaldehyde), containing coexisting Au3+ ions and Au⁰ nanoparticles, was prepared successfully by post-synthesis modification with ethylenediamine, salicylaldehyde and gold. Gold nanoparticles supported on MIL-101 (Au@MIL-...
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 48 14 شماره
صفحات -
تاریخ انتشار 2012