704-79-0

Upstream product

• 98-86-2 acetophenone 
• 124-38-9 carbon dioxide 
• 121-69-7 N,N-dimethyl-aniline 
• 98-83-9 isopropenylbenzene 
• 91-66-7 N,N-diethylaniline 
• 552-82-9 benzhydrylidene(methyl)amine 
• 209065-57-6 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetic acid 
• 1504-72-9 ethyl 3-phenylbut-2-enoate 
• 113426-20-3 C₁₄H₁₈O₂ 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 463-51-4 Ketene 
• 16251-77-7 3-Phenylbutyraldehyde 
• 201230-82-2 carbon monoxide 
• 3360-53-0 1-bromo-2-phenyl-1-propene 

Downstream Products

• 4593-90-2 3-phenylbutyric acid 
• 80854-59-7 β-methyl-4-nitrocinnamic acid 
• 102548-30-1 2,3-dibromo-3-phenyl-butyric acid 
• 98-83-9 isopropenylbenzene 
• 20698-78-6 (+/-)-3-Methoxy-3-phenyl-buttersaeure 
• 71001-35-9 (2-bromoprop-1-en-1-yl)benzene 
• 68204-17-1 3-phenylbut-2-enoyl chloride 
• 16428-64-1 rac.-β-Phenyl-β-deutero-buttersaeure 
• 3360-53-0 1-bromo-2-phenyl-1-propene 
• 3360-55-2 β-chloro-α-methylstyrene 
• 19647-26-8 (Z)-β-bromo-α-methylstyrene 
• 16917-35-4 (E)-(1-bromoprop-1-en-2-yl)benzene 
• 5670-65-5 1-nitro-2-phenylpropene 
• 70453-19-9 (E)-3-phenylbut-2-enoyl chloride 

Relevant academic research and scientific papers

Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed [3 + 2] Annulation of Vinyl Enolates with 1-Tosyl-2-vinylaziridine

The synergistic combination of N-heterocyclic carbene organocatalysis and transition-metal catalysis for a formal [3 + 2] annulation between 3-substituted but-2-enoates and 1-tosyl-2-vinylaziridine was developed. This cooperative strategy provides a facile and efficient access to various functionalized (E)-3-ethylidene-4-vinylpyrrolidin-2-ones in a regioselective and stereoselective manner. The preliminary asymmetric studies were also performed, which indicated a potential for enantioselective annulation of vinyl enolate intermediates with transition-metal-π-allyl species.

Construction of Multi-Substituted Benzenes via NHC-Catalyzed Reactions of Carboxylic Esters

A carbene-catalyzed ester activation reaction for the synthesis of multi-substituted benzenes is developed. Tetra-substituted benzene compounds are efficiently synthesized through this methodology. Compared with aldehyde substrates used in previous reports, the ester substrates used here are much more readily available and inexpensive. In addition, the TEMPO oxidant used here is more inexpensive than the quinones commonly used in related carbene-catalyzed reactions.

Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine

[Figure not available: see fulltext.] Reactions of 4-aryl-6-trifluoromethyl-2H-pyran-2-ones with sodium hydroxide followed by acidification provided the respective 6-hydroxy-5,6-dihydro derivatives, while the reactions of 4-aryl-6-trifluoromethyl-2H-pyran

One Photocatalyst, n Activation Modes Strategy for Cascade Catalysis: Emulating Coumarin Biosynthesis with (-)-Riboflavin

Generating molecular complexity using a single catalyst, where the requisite activation modes are sequentially exploited as the reaction proceeds, is an attractive guiding principle in synthesis. This requires that each substrate transposition exposes a catalyst activation mode (AM) to which all preceding or future intermediates are resistant. While this concept is exemplified by MacMillan's beautiful merger of enamine and iminium ion activation, examples in other fields of contemporary catalysis remain elusive. Herein, we extend this tactic to organic photochemistry. By harnessing the two discrete photochemical activation modes of (-)-riboflavin, it is possible to sequentially induce isomerization and cyclization by energy transfer (ET) and single-electron transfer (SET) activation pathways, respectively. This catalytic approach has been utilized to emulate the coumarin biosynthesis pathway, which features a key photochemical E → Z isomerization step. Since the ensuing SET-based cyclization eliminates the need for a prefunctionalized aryl ring, this constitutes a novel disconnection of a pharmaceutically important scaffold.

Iridium(III)-catalyzed regioselective direct arylation of sp2 C-H bonds with diaryliodonium salts

A regioselective direct arylation of arenes and olefins at the ortho position is reported. The key to the high selectivity is the appropriate choice of diaryliodonium salts as the arylating reagent in the presence of a cationic iridium(iii) catalyst. The coordination of the metal with an oxygen atom or a nitrogen atom and subsequent C-H activation allows for direct arylation with coupling partners. This reaction proceeds under mild reaction conditions and with a high tolerance of various functional groups including many halide functional groups.

Pd-Catalyzed α-Selective C-H Functionalization of Olefins: En Route to 4-Imino-β-Lactams

Pd-catalyzed α-olefinic C-H activation of simple α,β-unsaturated olefins has been developed. 4-imino-β-lactam derivatives were readily synthesized via activation of α-olefinic C-H bonds with excellent cis stereoselectivity. A wide range of heterocycles at the β-position are compatible with this reaction. The product of 4-imino-β-lactam derivatives can be readily converted to 2-aminoquinoline which exists extensively in pharmaceutical drugs and natural products.

Metal-Free Domino One-Pot Decarboxylative Cyclization of Cinnamic Acid Esters: Synthesis of Functionalized Indanes

Trifluoroacetic acid promoted unprecedented domino reaction for the synthesis of diverse indanes starting from simple cinnamic acid esters is described. Their formation can be explained via acid triggered decarboxylation of cinnamic acid esters and subsequent inter/intramolecular cyclization. Overall process involves in the intramolecular cleavage of two σ-bonds (C-O and C-C) and inter/intramolecular construction of two/one C-C σ-bond(s). Significantly, this protocol was successful without the aid of any metal salts.

N-Heterocyclic Carbene-Catalyzed Activation of Esters of N-Hydroxyphthalimide: A Highly Enantioselective Route to Chiral Dihydropyridinones Bearing an All Carbon Quaternary Stereogenic Center

An N-heterocyclic carbene-catalyzed highly enantioselective [3 + 3] annulation reaction of N-hydroxyphthalimide (NHPI) 3,3-disubstituted acrylates and N-Ts ketimines was developed. In most cases, the desired chiral dihydropyridinone products bearing an all carbon quaternary stereogenic center could be obtained in good yields with excellent enantioselectivities (>99% ee's), which demonstrated the NHPI acrylates as a kind of excellent substrate in NHC-catalysis.

Synthesis of coumarins via PIDA/I2-mediated oxidative cyclization of substituted phenylacrylic acids

A variety of functionalized coumarins were synthesized from substituted phenylacrylic acids via PIDA/I2-mediated and irradiation-promoted oxidative carbon-oxygen bond formation. Our studies show that the oxygen in the pendant carboxylic acid group cyclizes favorably to the aryl ring that is cis to it. The main advantages of this method include good functional group tolerance and the transition-metal-free characteristic. The Royal Society of Chemistry 2013.

Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: Access to pipecolic acid derivatives

The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.