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4676-39-5Relevant academic research and scientific papers
Isotopic changes during the synthesis of amphetamines
Carter, James F.,Titterton, Emma L.,Grant, Helen,Sleeman, Richard
, p. 2590 - 2591 (2002)
Observed variations in the δ13C and δ15N content of amphetamines are shown to be attributable to kinetic isotope effects during synthesis; chemical degradation and isotopic characterisation provides a means to identify the synthetic origins of illicit MDMA and other amphetamines.
Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols
Albarrán-Velo, Jesús,Gotor-Fernández, Vicente,Lavandera, Iván
, p. 4096 - 4108 (2021/08/19)
The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).
Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides
Li, Tingting,Hammond, Gerald B.,Xu, Bo
supporting information, p. 9737 - 9741 (2021/05/31)
A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C?C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.
An Efficient Palladium-Catalyzed α-Arylation of Acetone below its Boiling Point
Ledgard, Andrew J.,Martin, Fionna M.,Mutton, Simon P.,Richardson, Jeffery,Walton, Lesley
, (2020/07/24)
The monoarylation of acetone is a powerful transformation, but is typically performed at temperatures significantly in excess of its boiling point. Conditions described for performing the reaction at ambient temperatures led to significant dehalogenation when applied to a complex aryl halide. We describe our attempts to overcome both issues in the context of our drug-discovery program.
Nickel-Catalyzed Mono-Selective α-Arylation of Acetone with Aryl Chlorides and Phenol Derivatives
Amgoune, Abderrahmane,Derhamine, Sary Abou,Krachko, Tetiana,Monteiro, Nuno,Pilet, Guillaume,Schranck, Johannes,Tlili, Anis
supporting information, p. 18948 - 18953 (2020/09/01)
The challenging nickel-catalyzed mono-α-arylation of acetone with aryl chlorides, pivalates, and carbamates has been achieved for the first time. A nickel/Josiphos-based catalytic system is shown to feature unique catalytic behavior, allowing the highly selective formation of the desired mono-α-arylated acetone. The developed methodology was applied to a variety of (hetero)aryl chlorides including biologically relevant derivatives. The methodology has been extended to the unprecedented coupling of acetone with phenol derivatives. Mechanistic studies allowed the isolation and characterization of key Ni0 and NiII catalytic intermediates. The Josiphos ligand is shown to play a key role in the stabilization of NiII intermediates to allow a Ni0/NiII catalytic pathway. Mechanistic understanding was then leveraged to improve the protocol using an air-stable NiII pre-catalyst.
Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process
González-Martínez, Daniel,Gotor, Vicente,Gotor-Fernández, Vicente
, p. 2582 - 2593 (2019/05/15)
Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).
Carbazolyl phosphorus ligand as well as preparation method and application thereof
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Paragraph 0167; 0168; 0169; 0170; 0171; 0172, (2017/07/04)
The invention is suitable for the technical fields of organic compounds and synthesis, and provides a carbazolyl phosphorus ligand as well as a preparation method and application thereof. The carbazolyl phosphorus ligand is one of a compound 1, a compound 2 and a compound 3 with structures shown by a formula 1, a formula 2 and a formula 3 (shown in the description) respectively, wherein R1 is phenyl or alkyl, R2, R3, R4, R5, R6, R7, R8 and R9 independently are one of hydrogen, C5-C10 alkyl, methoxyl, oxymethyl, ethyoxyl, phenyl, fluorine group, and pyridyl; and R2, R3, R4, and R5 cannot be hydrogen at the same time.
Oxidative Dehomologation of Aldehydes with Oxygen as a Terminal Oxidant
Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
, p. 6760 - 6762 (2017/12/26)
A mild, efficient protocol for oxidative cleavage of C-C bonds in aldehydes has been developed that employs alkali metal hydrides as reagents and oxygen from air as a terminal oxidant. The method is applicable to a broad substrate range.
Preparation of a highly congested carbazoyl-derived p,n-type phosphine ligand for acetone monoarylations
Fu, Wai Chung,Zhou, Zhongyuan,Kwong, Fuk Yee
, p. 1553 - 1558 (2016/06/09)
We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)2/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N-Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species.
Sassafras oil, carrot bits and microwaves: Green lessons learned from the formal total synthesis of (-)-talampanel
Omori, Alvaro Takeo,De Oliveira, Camila De Souza,Andrade, Kleber Tellini,Capeletto, Marina Gon?alves
, p. 103563 - 103565 (2015/12/23)
A formal total synthesis of (-)-talampanel (1), a 2,3-benzodiazepine is described. This work was undertaken to utilize greener reaction conditions. Safrole (a renewable source) was converted to (1) in eight steps, including an enantioselective bioreduction using carrots as the key step. Microwave irradiation was also used to perform three reaction steps.