1233735-99-3

Upstream product

• 7164-98-9 1-phenylimidazole 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 103-82-2 phenylacetic acid 

Downstream Products

• 1233735-65-3 (Z)-cyclohex-2-enyl-2-phenyl-1-(1-phenyl-1H-imidazol-2-yl)vinyl carbonate 

Relevant academic research and scientific papers

Catalytic Enantioselective Oxidative Homocoupling of 2-Acyl Imidazoles

A diastereoselective and enantioselective construction of 2,3-disubstituted 1,4-dicarbonyl compounds is reported. Nishiyama's RuPhebox complex (2.0 mol% catalyst loading) serves as a chiral Lewis acid catalyst in conjunction with BrCCl3 and a base for the oxidative homocoupling of 2-acyl imidazoles via the stereocontrolled reaction of intermediate Ru enolates with in situ brominated 2-acyl imidazoles. Cleavage of the achiral imidazole auxiliary provides optically active 2,3-disubstituted succinic acids which are useful intermediates in the synthesis of chiral compounds like the natural product class of lignans. (Figure presented.).

Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes

Chiral-at-metal RhIII complexes catalyze the efficient enantioselective Mannich reaction of 2-acyl imidazoles with 1,3,5-triazinanes, affording the corresponding adducts in 81–99 % yield with up to >99 % enantioselectivity. This protocol performs with 0.1 mol-% of RhIII complex on gram scale without any loss in enantioselectivity.

Octahedral iridium complex catalyzed α-chlorination of 2-acyl imidazoles with tosyl chloride

An efficient and catalytic α-chlorination of 2-acyl imidazoles with readily available tosyl chloride catalyzed by an octahedral iridium complex under mild condition was reported. A range of 2-acyl imidazoles were converted to their corresponding α-chlorin

A Rhodium Catalyst Superior to Iridium Congeners for Enantioselective Radical Amination Activated by Visible Light

A bis-cyclometalated rhodium(III) complex catalyzes a visible-light-activated enantioselective α-amination of 2-acyl imidazoles with up to 99 % yield and 98 % ee. The rhodium catalyst is ascribed a dual function as a chiral Lewis acid and, simultaneously, as a light-activated smart initiator of a radical-chain process through intermediate aminyl radicals. Notably, related iridium-based photoredox catalysts reported before were unsuccessful in this enantioselective radical C?N bond formation. The surprising preference for rhodium over iridium is attributed to much faster ligand-exchange kinetics of the rhodium complexes involved in the catalytic cycle, which is crucial to keep pace with the highly reactive and thus short-lived nitrogen-centered radical intermediate.

Visible-Light-Activated Enantioselective Perfluoroalkylation with a Chiral Iridium Photoredox Catalyst

A visible-light-activated enantioselective radical perfluoroalkylation of 2-acyl imidazoles with perfluoroalkyl iodides (CF3I, C3F7I, C4F9I, C6F13I, C8F17I

Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes

The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.

Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst

Abstract A single chiral octahedral iridium(III) complex is used for visible light activated asymmetric photoredox catalysis. In the presence of a conventional household lamp and under an atmosphere of air, the oxidative coupling of 2-acyl-1-phenylimidazoles with N,N-diaryl-N-(trimethylsilyl)methylamines provides aminoalkylated products in 61-93 % yields with high enantiomeric excess (90-98 % ee). Notably, the iridium center simultaneously serves three distinct functions: as the exclusive source of chirality, as the catalytically active Lewis acid, and as a central part of the photoredox sensitizer. This conceptionally simple reaction Scheme may provide new avenues for the green synthesis of non-racemic chiral molecules. Doing it all alone: A chiral iridium complex is used for visible light activated asymmetric photoredox catalysis by combining photoinduced oxidation with asymmetric Ci-C bond formation.

Enantioselective, catalytic trichloromethylation through visible-light-activated photoredox catalysis with a chiral iridium complex

An enantioselective, catalytic trichloromethylation of 2-acyl imidazoles and 2-acylpyridines is reported. Several products are formed with enantiomeric excess of ≥99%. In this system, a chiral iridium complex serves a dual function, as a catalytically active chiral Lewis acid and simultaneously as a precursor for an in situ assembled visible-light-triggered photoredox catalyst.

Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents

A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.