81616-82-2

Upstream product

• 591-50-4 iodobenzene 
• 127-19-5 N,N-dimethyl acetamide 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 
• 18925-69-4 N,N-dimethyl-2-phenylacetamide 
• 492-38-6 2-phenylacrylic acid 
• 81616-78-6 N, N-dimethyl-2-phenylacrylamide 
• 103-80-0 phenylacetyl chloride 
• 2680-03-7 N,N-Dimethylacrylamide 
• 68-12-2 N,N-dimethyl-formamide 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 611-74-5 N,N-dimethylbenzamide 
• 760-79-2 N,N-dimethylbutyramide 

Downstream Products

• 492-37-5 hydratropic acid 
• 54191-82-1 N,N-dimethyl-2-phenylpropanethioamide 
• 78075-75-9 N-((S)-α-Phenylethyl)-3(R)-methyl-3(R),4(S)-diphenylazetidin-2-one 
• 78147-87-2 N-((S)-α-Phenylethyl)-3(R)-methyl-3(R),4(R)-diphenylazetidin-2-one 
• 78147-86-1 N-((S)-α-Phenylethyl)-3(S)-methyl-3(S),4(S)-diphenylazetidin-2-one 
• 78147-85-0 N-((S)-α-Phenylethyl)-3(S)-methyl-3(S),4(R)-diphenylazetidin-2-one 
• 63646-74-2 α-Chlor-β-methyl-β-phenyl-N,N-dimethylvinylamin 
• 1357283-11-4 3-(dimethylamino)-2-methyl-3-oxo-2-phenylpropanoic acid 
• 72087-76-4 dimethyl-(2-phenyl-propenyl)-amine 
• 2042-85-5 1,2-diphenylpropan-1-one 

Relevant academic research and scientific papers

Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent "Ene"-Reductases

Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor-acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within "ene"-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.

Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)

Support by the Department of Energy was inadvertently left out of the Acknowledgments and a coauthor's name was misspelled in the Supporting Information. The scientific part of the manuscript remains unchanged. The complete correct Acknowledgment paragraph is as follows.

Preparation of alkylated compounds using the trialkylphosphate

[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications.

Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction

The palladium-catalyzed, α-selective hydroarylation of acrylates and acrylamides is reported. Under optimized conditions, this method is highly tolerant of a wide range of substrates including those with base sensitive functional groups and/or multiple enolizable carbonyl groups. A detailed mechanistic study was undertaken, and the high selectivity of this transformation was shown to be enabled by the formation of a [PdII(Ar)(H)] intermediate, which performs selective hydride insertion into the β-position of α,β-unsaturated carbonyl compounds.

Selective α-Monomethylation by an Amine-Borane/N,N-Dimethylformamide System as the Methyl Source

A new and practical α-monomethylation strategy using an amine-borane/N,N-dimethylformamide (R3N-BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α-monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N-BH3 donated the remaining two hydrogen atoms. Such a unique reaction pathway enabled controllable assemblies of CDH2-, CD2H-, and CD3- units using Me2NH-BH3/d7-DMF, Me3N-BD3/DMF and Me3N-BD3/d7-DMF systems, respectively. Further application of this method to the facile synthesis of anti-inflammatory flurbiprofen and its varied deuterium-labeled derivatives was demonstrated.

Palladium-Catalyzed Hydrocarbonylative C-N Coupling of Alkenes with Amides

An efficient palladium-catalyzed hydrocarbonylative C-N coupling of alkenes with amides has been developed. The reaction was performed via hydrocarbonylation of alkenes, followed by acyl metathesis with amides. Both intermolecular and intramolecular react

Pd-Catalyzed Site-Selective p-Hydroxyphenyloxylation of Benzylic α-C(sp3)-H Bonds with 1,4-Benzoquinone

A Pd-catalyzed, site-selective p-hydroxyphenyloxylation of benzylic α-C(sp3)-H bonds with 1,4-benzoquinone using thioamide as a directing group is reported. 1,4-Benzoquinone is employed as the p-hydroxyphenyloxy source without extra oxidants. T

Alternative synthesis of 2-arylpropanoic acids from enolate and aryl halides

Arylpropanoic acids, a type of non-steroidal antiinflammatory drug, have been prepared in liquid ammonia by photo-radical nucleophilic substitution of halogenoarenes with sodium N,N-dimethylacetamide enolate followed by methylation and hydrolysis.Rapid substitution occured in many cases with good to excellent yields of arylpropanoic acids.The title compounds have also been prepared by arylation of sodium acetone enolate with methylation and oxidation in a haloform reaction.