51086-46-5

Upstream product

• 144899-78-5 (<2,2-D₂>-2-Phenylethyl)malonsaeure 
• 33712-34-4 benzyl-d2 chloride 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 93-58-3 benzoic acid methyl ester 
• 73073-37-7 (<2,2-D₂>-2-Phenylethyl)malonsaeure-diethylester 
• 51086-45-4 2,2-dideuterio-2-phenyl-ethanol 
• 1076-07-9 2,2-dideuterio-2-phenyl-acetic acid 
• 23088-37-1 2,2-d₂-phenethyl bromide 
• 1821-12-1 4-Phenylbutyric acid 

Downstream Products

• 1021878-01-2 methyl-4-phenylbutanoate-4,4-d₂ 

Relevant academic research and scientific papers

An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides

The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C - H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C - H bonds was also achieved with remarkable tolerance to the C=C and C=C bonds.

Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones

We report the Ru-Catalyzed enantioselective annulation of 1,4,2-Dioxazol-5-Ones to furnish ?-Lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-Withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- A nd enantioselectivities; the competing Curtius-Type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the Ca?C and Ca‰iC bonds.

Catalytic C-H Amination Mediated by Dipyrrin Cobalt Imidos

Reduction of (ArL)CoIIBr (ArL = 5-mesityl-1,9-(2,4,6-Ph3C6H2)dipyrrin) with potassium graphite afforded the novel CoI synthon (ArL)CoI. Treatment of (ArL)CoI with a stoichiometric amount of various alkyl azides (N3R) furnished three-coordinate CoIII alkyl imidos (ArL)Co(NR), as confirmed by single-crystal X-ray diffraction (R: CMe2Bu, CMe2(CH2)2CHMe2). The exclusive formation of four-coordinate cobalt tetrazido complexes (ArL)Co(κ2-N4R2) was observed upon addition of excess azide, inhibiting any subsequent C-H amination. However, when a weak C-H bond is appended to the imido moiety, as in the case of (4-azido-4-methylpentyl)benzene, intramolecular C-H amination kinetically outcompetes formation of the corresponding tetrazene species to generate 2,2-dimethyl-5-phenylpyrrolidine in a catalytic fashion without requiring product sequestration. The imido (ArL)Co(NAd) exists in equilibrium in the presence of pyridine with a four-coordinate cobalt imido (ArL)Co(NAd)(py) (Ka = 8.04 M-1), as determined by 1H NMR titration experiments. Kinetic studies revealed that pyridine binding slows down the formation of the tetrazido complex by blocking azide coordination to the CoIII imido. Further, (ArL)Co(NR)(py) displays enhanced C-H amination reactivity compared to that of the pyridine-free complex, enabling higher catalytic turnover numbers under milder conditions. The mechanism of C-H amination was probed via kinetic isotope effect experiments [kH/kD = 10.2(9)] and initial rate analysis with para-substituted azides, suggesting a two-step radical pathway. Lastly, the enhanced reactivity of (ArL)Co(NR)(py) can be correlated to a higher spin-state population, resulting in a decreased crystal field due to a geometry change upon pyridine coordination.

Efficient and convenient heterogeneous palladium-catalyzed regioselective deuteration at the benzylic position

The Pd/C-catalyzed efficient and regioselective hydrogen-deuterium (H-D) exchange reaction on the benzylic site proceeded in D2O in the presence of a small amount of H2 gas. The use of the Pd/C-ethylenediamine complex [Pd/C(en)] as a catalyst instead of Pd/C led to the efficient deuterium incorporation into the benzylic site of Obenzyl protective groups without hydrogenolysis. These H-D exchange reactions provide a post synthetic and D2-gas-free deuterium-labeling method on a wide variety of benzylic sites using D2O as the deuterium source and heterogeneous Pd/C or Pd/C(en) as a reusable heterogeneous palladium catalyst under mild and neutral conditions.

Raney Co-Al Alloy, an Efficient Catalyst for the Selective Incorporation of Deuterium Atoms at the Benzylic Position of Aromatic Compounds

By using Raney Co-Al in 20% Na2CO3-D2O solution, deuterium atoms can be selectively incorporated into the benzylic position of aromatic compounds in high deuterium content.

Hydrogen Transfer Reactions, Part 2. Radical Mechanism of Thermal Disproportionation of 1,2-Dihydronaphthalene

In the thermal disproportionation of 1,2-dihydronaphthalene (1) both hydrogen abstraction and addition are stereo-unspecific radical reactions.An electrocyclic mechanism was excluded.