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Relevant academic research and scientific papers

Amines based on electron-rich fluoroaromatic hydrocarbons, and preparation method of amines

The invention provides amines based on electron-rich fluoroaromatic hydrocarbons, and a preparation method of the amines. The structure of the amines is as shown in a formula I. The invention also provides the preparation method of the amines based on the

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex

Thanks to a highly active catalyst, the scope of the (cyclopentadienone)iron complex-promoted 'hydrogen-borrowing' (HB) amination has been expanded to secondary alcohols, which had previously been reported to react only in the presence of large amounts of co-catalysts. A range of cyclic and acyclic secondary alcohols were reacted with aromatic and aliphatic amines giving fair to excellent yields of the substitution products. The catalyst was also able to promote the cyclization of diols bearing a secondary alcohol group with primary amines to generate saturated N-heterocycles.

Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations

Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.

Efficient Synthesis of Amines by Iron-Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination

Here we report the catalytic transfer hydrogenation (CTH) of non-activated imines promoted by a Fe-catalyst in the absence of Lewis acid co-catalysts. Use of the (cyclopentadienone)iron complex 1, which is much more active than the classical ‘Kn?lker complex’ 2, allowed to reduce a number of N-aryl and N-alkyl imines in very good yields using iPrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe-complex as the only catalyst has little precedents. Based on this methodology, we developed a one-pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. (Figure presented.).

Chloride-tolerant gold(I)-catalyzed regioselective hydrochlorination of alkynes

We have developed a highly regioselective homogeneous gold(I)-catalyzed anti-hydrochlorination of unactivated alkynes at room temperature. We have overcome the incompatibility between conventional cationic gold catalysts and chloride by using a hydrogen-b

Commercial Supported Gold Nanoparticles Catalyzed Alkyne Hydroamination and Indole Synthesis

Commercial gold nanoparticles supported on titanium dioxide (TiO2) were found to be a highly efficient catalyst for alkyne hydroamination. Terminal alkynes could easily undergo intermolecular hydroamination with low catalyst loadings (0.2 mol% Au) under solvent-free conditions. Indoles were efficiently synthesized using microwave heating through intramolecular hydroamination. (Figure presented.).

Iron-catalyzed amination of alcohols assisted by Lewis acid

An efficient Lewis acid-assisted, iron-catalyzed amination of alcohols using borrowing hydrogen methodology was developed. In particular, silver fluoride was identified to be a highly effective additive to overcome the low efficiency in the amination of secondary alcohols catalyzed by Kn?lker's complex.

Titanium complexes supported by imidazo[1,5-a]pyridine-containing pyrrolyl ligand as catalysts for hydroamination and polymerization reactions, and as an antitumor reagent

A new imidazo[1,5-a]pyridine-containing pyrrolyl ligand HL (HL = 3-(1H-pyrrol-2-yl)imidazo[1,5-a]pyridine) was synthesized and employed in the organometallic chemistry of titanium. The syntheses, structures, catalytic properties and antitumor activity of three titanium complexes supported by HL are reported. Reactions of Ti(NMe2)4 and Ti(NEt2)4 with 2 equivalents of HL, led to the production of titanium bisamido complexes TiL2(NMe2)2 (1) and TiL2(NEt2)2 (2), respectively. Treatment of Ti(OiPr)4 with 2 equivalents of HL resulted in the formation of TiL2(OiPr)2 (3). All complexes were characterized by elemental analyses and NMR studies. The solid-state structures of 2 and 3 were further established by single X-ray crystallography. The titanium bisamido complexes 1 and 2 are shown to be good pre-catalysts for the hydroamination of alkynes. Complex 1 was found to be an active catalyst for the ring-opening polymerization of ε-caprolactone. The cytotoxicity activities of 3 towards the tumor cells HCT-116, PC3 and MCF-7 were measured. Complex 3 exhibited good antitumor properties.

One-pot transformation of alkynes into alcohols and amines with formic acid

Alkynes are converted into alcohols and amines through a formic acid-participated alkyne-to-ketone transformation and transfer hydrogenation process. The reaction proceeds well under aqueous conditions, furnishing chiral alcohols directly from alkynes for the first time.

Fast reductive amination by transfer hydrogenation "on water"

Reductive amination of various ketones and aldehydes by transfer hydrogenation under aqueous conditions has been developed, by using cyclometallated iridium complexes as catalysts and formate as hydrogen source. The pH value of the solution is shown to be critical for a high catalytic chemoselectivity and activity, with the best pH value being 4.8. In comparison with that in organic solvents, the reductive amination in an aqueous phase is faster, and the molar ratio of the substrate to the catalyst (S/C) can be set as high as 1×105, the highest S/C value ever reported in reductive amination reactions. The catalyst is easy to access and the reaction is operationally simple, allowing a wide range of ketones and aldehydes to react with various amines in high yields. The protocol provides a practical and environmental friendly new method for the synthesis of amine compounds. Greener amine synthesis: A versatile reductive amination protocol has been developed. By using an iridium catalyst in water, a broad range of ketones and aldehydes react with amines to afford various new amines in good yields (see scheme), with molar ratios of the substrate to the catalyst (S/C) as high as 1×10 5. The pH of the reaction solution plays a key role, regulating both the catalytic activity and the selectivity. Copyright