51086-45-4

Upstream product

• 120035-25-8 [²H]-phenylacetic acid ethyl ester 
• 60-12-8 2-phenylethanol 
• 93-89-0 benzoic acid ethyl ester 
• 100-42-5 styrene 
• 83-13-6 diethyl 2-phenylmalonate 
• 33712-34-4 benzyl-d2 chloride 
• 93-58-3 benzoic acid methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 
• 114-70-5 sodium phenylacetate 
• 103-82-2 phenylacetic acid 
• 51271-29-5 [1',1'-2H₂]benzyl bromide 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 1076-07-9 2,2-dideuterio-2-phenyl-acetic acid 

Downstream Products

• 23088-37-1 2,2-d₂-phenethyl bromide 
• 50561-93-8 1-fluoro-2-phenylathane-2,2-d₂ 
• 51086-44-3 phenylacetaldehyde-2,2-d₂ 
• 1204222-65-0 (2,2-dibromocyclopropyl-1-d)benzene 
• 1204222-71-8 4-bromo-1-chloro-2-(4-(cyclopropyl-1-d)benzyl)benzene 
• 1204222-73-0 4-bromo-1-chloro-2-((4-(cyclopropyl-1-d)phenyl)methyl-d2)benzene 
• 1204222-69-4 4-bromo-1-chloro-2-(4-(2,2-dibromocyclopropyl-1-d)benzyl)benzene 
• 1204222-67-2 (5-bromo-2-chlorophenyl)(4-(2,2-dibromocyclopropyl-1-d)phenyl)methanone 
• 1204222-77-4 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-(cyclopropyl-1-d)phenyl)methyl-d2)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1204222-75-2 (3R,4S,5S,6R)-2-(4-chloro-3-((4-(cyclopropyl-1-d)phenyl)methyl-d2)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 60604-09-3 3-phenylpropane-3,3-d₂ 
• 116503-62-9 C₂₆H₂₁⁽²⁾H₂P 
• 116503-63-0 1,4-diphenyl-2-butene-1,1,4,4-d4 
• 116503-64-1 1,4-diphenyl-2-butene-1,1-d2 

Relevant academic research and scientific papers

Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.

Enantioselective Copper(I)/Chiral Phosphoric Acid Catalyzed Intramolecular Amination of Allylic and Benzylic C?H Bonds

Radical-involved enantioselective oxidative C?H bond functionalization by a hydrogen-atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)?H bond amination remains a formidable challenge. To address this problem, described herein is a dual CuI/chiral phosphoric acid (CPA) catalytic system for radical-involved enantioselective intramolecular C(sp3)?H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4-methoxy-NHPI (NHPI=N-hydroxyphthalimide) as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved.

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides

A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which pro

Nickel-Catalyzed Allylic C(sp2)–H Activation: Stereoselective Allyl Isomerization and Regiospecific Allyl Arylation of Allylarenes

Stereoselective allyl isomerization and regiospecific allyl arylation reactions of allylarenes with a catalytic system comprising nickel(II) with an aryl Grignard reagent were studied. Both reactions are triggered by allylic internal C(sp2)–H activation by in-situ-formed Ni0, which is inserted into the C–H bond at the 2-position of the allyl moiety without a directing group. The isomerization of allylarene to 1-propenylarene favors the E isomer and proceeds with quantitative conversion. The arylation takes place through oxidative cross-coupling of allylarenes with excess Grignard reagent. It occurs regiospecifically at the position of C(sp2)–H activation and represents a new method for the synthesis of 1,1-disubstituted olefins. The results of deuterium labeling experiments reveal an alkenyl/alkyl mechanism involving allylic internal C(sp2)–H activation and multiple intermolecular 1,2-, 1,3-, and 2,3-hydride shifts. These methods represent new approaches to the functionalization of olefins, and the mechanistic investigations could be helpful for the discovery and design of new strategies for olefin functionalization.

Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

A highly practical and general palladium-catalyzed methodology for the α,β-dehydrogenation of esters and nitriles is reported. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of α,β-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible β-hydride elimination and turnover-limiting, propene-forming reductive elimination.

CATALYTIC ANTI-MARKOVNIKOV OXIDATION AND HYDRATION OF OLEFINS

The disclosure provides a dual-catalysis system for direct conversion of olefins to alcohols. The cooperative catalytic system contains one oxidizing catalyst and one transfer-hydrogenation catalyst. A wide variety of olefins, including aromatic and aliphatic olefins, can be used as the reactant. The transformation proceeds with anti-Markovnikov selectivity, and in some aspects provides primary alcohols as major products. The disclosure further provides a system for oxidation of olefins with anti-Markovnikov selectivity.

DEUTERATED BENZYLBENZENE DERIVATIVES AND METHODS OF USE

Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions that are affected by SGLT inhibition.

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.

Efficient H/D exchange reactions of alkyl-substituted benzene derivatives by means of the Pd/C-H2-D2O system

A method for efficient and extensive H/D exchange of substituted benzene derivatives which is catalyzed by heterogeneous Pd/C in D2O as a deuterium source under hydrogen atmosphere is described. Multideuterium incorporation into unactivated linear or branched alkyl chains that bear a carboxyl, hydroxyl, ether, ester, or amide moiety and are connected with a benzene ring was achieved by using the Pd/C-H2-D2O system. The present method does not require expensive deuterium gas or any special equipment.