51831-56-2

Upstream product

• 1271-55-2 acetylferrocene 
• 100-51-6 benzyl alcohol 
• 1277-49-2 1-ferrocenylethanol 
• 1273-86-5 1-ferrocenylmethanol 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the α-alkylation of ketones with primary alcohols

We report herein the synthesis of four new Pd-PEPPSI complexes with backbone-modified N-heterocyclic carbene (NHC) ligands and their application as catalysts in the α-alkylation of ketones with primary alcohols using a borrowing hydrogen process and tandem Suzuki-Miyaura coupling/α-alkylation reactions. Among the synthesized Pd-PEPPSI complexes, complex2chaving 4-methoxyphenyl groups at the 4,5-positions and 4-methoxybenzyl substituents on the N-atoms of imidazole exhibited the highest catalytic activity in the α-alkylation of ketones with primary alcohols (18 examples) with yields reaching up to 95%. Additionally, complex2cwas demonstrated to be an effective catalyst for the tandem Suzuki-Miyaura-coupling/α-alkylation of ketones to give biaryl ketones with high yields. The heterogeneous nature of the present catalytic system was verified by mercury poisoning and hot filtration experiments. Moreover, the formation of NHC-stabilized Pd(0) nanoparticles during the α-alkylation reactions was identified by advanced analytical techniques.

Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese

A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.

Ligand-controlled phosphine-free Co(II)-catalysed cross-coupling of secondary and primary alcohols

Cobalt(II) complexes (5 mol% Co) bearing phosphine-free N?N?N pincer ligands efficiently catalyze C–C coupling of secondary and primary alcohols to selectively form α-alkylated ketones with a good functional group compatibility using NaOH (20 mol%) as a base at 120 °C. The NH group on the N?N?N–Co(II) precatalyst controls the activity and selectivity. This simple catalytic system is involved in the synthesis of quinolones via the dehydrogenative annulation of 2-aminobenzyl alcohols with secondary alcohols.

Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.

Iridium(III)- benzoxazolyl and benzothiazolyl phosphine ligands catalyzed versatile alkylation reactions with alcohols and the synthesis of quinolines and indole

A series of benzoxazolyl and benzothiazolyl phosphine ligands 4a-4g were synthesized and characterized, which prepared from commercially available 2-aminophenol/2-aminobenzenethiol and 2-bromobenzaldehyde via cyclization and phosphination. The representative ligands 4c and 4e were determined by single-crystal X-ray diffraction. The corresponding iridium complexes could be generated in situ when [Cp*IrCl2]2 (Cp* = pentamethylcyclopentadienyl) encountered ligands. The molecular structures of complexes 5c and 5e were crystallographically characterized. The dihedral angles of N (1)-C (1)-C (8)-C (9) showed an increasing twist compared with the corresponding ligand. The iridium (III) catalysts were screened, [Cp*IrCl2]2/4a proved to be the optimal catalyst, which exhibited efficient catalytic activity toward versatile alkylations including ketones, secondary alcohols and amines with primary alcohols. Additionally, the synthesis of quinolines from ketones with 2-aminobenzyl alcohol by intermolecular cyclization and indole from 2-(2-aminophenyl)ethanol by intramolecular cyclization were achieved under the optimized conditions.

Triphenylphosphine [...]link iridium hydrogen adduct and its preparation and use

The invention discloses a benzo-quinoline triphenylphosphine ring iridium hydride adduct. The compound has the general formula in the specification, wherein R is H,-CH3,-OCH3,-C6H5 or-CHO, and R is positioned in the position of 3, 5, 6 or 8 of benzo-quinoline. The preparation steps of the compound are as follows: taking a benzo-quinoline derivative, iridium trichloride and triphenylphosphine, adding into a solvent, performing heating reflux under gas protection, and filtering after the end of the reaction to obtain the benzo-quinoline triphenylphosphine ring iridium hydride adduct. The prepared benzo-quinoline triphenylphosphine ring iridium hydride adduct is a high-activity catalyst which can catalyze the reaction of aryl alkyne and aryl benzyl alcohol to obtain an aryl ketone compound. The benzo-quinoline triphenylphosphine ring iridium hydride adduct is taken as a metal catalyst, the using quantity of the catalyst is small, a cheap weak base is used, and then the reaction of the aryl alkyne and the aryl benzyl alcohol can be catalyzed efficiently. The method has the advantages of mild reaction conditions, wide range of reaction substrates, economy, high efficiency and the like, and further has important application values.

An efficient heterogenized palladium catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols

A silica supported palladium-NiXantphos complex is reported as an efficient and a high turnover heterogeneous catalyst for the N-alkylation of amines and the α-alkylation of ketones using readily available alcohols under neat conditions at 120-140 °C following hydrogen borrowing strategy. The catalyst is easily separable and offers negligible amount of palladium leaching (0.01 ppm). A high turnover number of about 46000 for the N-alkylation of amines and 4400 for the α-alkylation of ketones were achieved in the respective single batch reactions. The catalyst is recyclable up to four times without appreciable change in catalytic performance.

Triphenylphosphine-cyclometallated iridium(III) pyrimidine complexes: Synthesis, crystal structures and application in α-alkylation of ketones with alcohols

Two triphenylphosphine (PPh3)-cyclometallated iridium(III) pyrimidine complexes Ir(NDMP)2PPh3Cl 1 and Ir(NDMP)(PPh3)2Cl2 2 (NDMP = 2-(2-naphthyl)-4,6- dimethyl-pyrimidine) were synthesized and characterized by NMR, IR, ESI-MS, and elemental analysis. Additionally, their detailed structures have been determined by X-ray single-crystal diffraction. The complex 1 was a PPh3-biscyclometalated Ir(III) complex, while 2 was a PPh 3-monocyclometalated Ir(III) complex. These complexes were found to be efficient catalysts for α-alkylation of ketones with alcohols.