1361006-38-3

Upstream product

• 138343-84-7 [2-(2-Oxo-3-phenyl-propyl)-phenyl]-carbamic acid tert-butyl ester 
• 120-72-9 indole 
• 100-39-0 benzyl bromide 
• 3377-71-7 N-benzylindole 
• 3377-72-8 2-benzylindole 

Relevant academic research and scientific papers

Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles

The first application of binaphthyl-stabilized palladium nanoparticles (Bin-PdNPs) with chiral modifiers in asymmetric hydrogenation of N-heteroaromatics is revealed. With an appropriate ratio of R-BINAP/Bin-PdNPs used, the pre-prepared chiral nanocatalyst achieves asymmetric hydrogenations of 2-substituted quinolines with good to excellent yields and moderate enantioselectivities, which showed superior catalytic properties to the R-BINAP/Pd complex. Moreover, this protocol is also applicable to 2-substituted indoles.

Method for synthesizing chiral indoline through palladium catalyzed asymmetric hydrogenation of indole generated in situ

The invention discloses a method for synthesizing chiral indoline through palladium-catalyzed asymmetric hydrogenation of indole generated in situ. The method is characterized in that an indole compound generated in situ is subjected to asymmetric hydrogenation by using 1-5 mol% of a palladium catalyst and adding 1-2.0 equev acid to obtain a corresponding chiral indoline compound, wherein the enantiomeric excess can reach 96% at most. According to the invention, the method is simple and convenient to operate, practical, easy to implement, high in yield, environmentally friendly, available in catalyst business and mild in reaction condition, and has potential practical application value.

Br?nsted-Acid-Promoted Rh-Catalyzed Asymmetric Hydrogenation of N-Unprotected Indoles: A Cocatalysis of Transition Metal and Anion Binding

The incorporation of Br?nsted acid, thiourea anion binding, and transition metal catalysis enables an efficient method to synthesize chiral indolines via hydrogenation of indoles. Catalyzed by a rhodium/ZhaoPhos complex, asymmetric hydrogenation of unprotected indoles is performed smoothly with excellent enantioselectivities (up to 99% ee, up to 400 TON). Br?nsted acid HCl activates indoles to form iminium ion intermediates. Mechanistic studies support the assumption that anion binding plays a crucial role as a secondary interaction. DFT calculations reveal an outer-sphere mechanism in this chemical transformation.

Asymmetric hydrogenation of unprotected indoles using iridium complexes derived from P-OP ligands and (reusable) Bronsted acids

Unprotected indoles have been efficiently converted to enantiomerically enriched indolines (up to 91% ee) by a stepwise process: (reusable) Bronsted acid-mediated C=C isomerisation and asymmetric hydrogenation using enantioselective iridium catalysts derived from P-OP ligands. This straightforward combination of (reusable) Bronsted acids, which activate the indole ring for hydrogenation by breaking its aromaticity, and enantiomerically pure [Ir(P-OP)]+ complexes as hydrogenation catalysts affords the resulting indolines with high enantioselectivities.

Highly enantioselective hydrogenation of N-unprotected indoles using (S)-C10-BridgePHOS as the chiral ligand

(S)-C10-BridgePHOS was successfully applied to a highly efficient Pd-catalyzed enantioselective hydrogenation of substituted indoles. The methodology was suitable for the hydrogenation of indoles substituted at the 2-, 3- and 2,3-positions. Products were obtained in quantitative conversion and up to 98% ee. The role the 2-position substituent plays in the hydrogenation process has been proposed. The methodology could be used as an alternative method to synthesize extremely important chiral indolines from N-unprotected indoles.

A new electronically deficient atropisomeric diphosphine ligand (S)-CF 3O-BiPhep and its application in asymmetric hydrogenation

A new electronically deficient atropisomeric diphosphine ligand (S)-CF 3O-BiPhep was synthesized from 1-bromo-3-(trifluoromethoxy)benzene in high yield. The key steps included oxidative coupling with anhydrous ferric chloride and optical resolution by (+)-DMTA. The ligand afforded high performance for Ir-catalyzed asymmetric hydrogenation of quinolines with ee up to 92% and TON up to 25,000. It was also successfully applied to the Pd-catalyzed asymmetric hydrogenation of simple indoles with ee up to 87% and Rh-catalyzed asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone with 97% ee.

Direct asymmetric hydrosilylation of indoles: Combined Lewis base and bronsted acid activation

Quite a pair: The first organocatalytic direct asymmetric reduction of unprotected 1H-indoles to chiral indolines has been developed. The reaction proceeds through the generation of electrophilic indolenium ions by a Bronsted acid, and then chiral Lewis base (1) mediated enantioselective hydride transfer with HSiCl3. A variety of chiral indolines were obtained with moderate to excellent enantioselectivity. MOM=methoxymethyl. Copyright