Month: November 2022

Wu, Zhao published the artcileAsymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination, Safety of 2-Methoxy-5-methylphenylboronic acid, the main research area is amine rhodium catalyst tandem chemoselective enantioselective reductive amination.

A general asym. route for the one-pot synthesis of chiral γ-branched amines through the highly enantioselective isomerization of allylamines, followed by enamine exchange and subsequent chemoselective reduction was reported. This protocol was suitable for establishing various tertiary stereocenters, including those containing dialkyl, diaryl, cyclic, trifluoromethyl, difluoromethyl, and silyl substituents, which allowed for a rapid and modular synthesis of many chiral γ-branched amines. To demonstrate the synthetic utility, Terikalant and Tolterodine were synthesized using this method with high levels of enantioselectivity.

Nature Communications published new progress about Amines, unsaturated Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 127972-00-3 belongs to class ethers-buliding-blocks, name is 2-Methoxy-5-methylphenylboronic acid, and the molecular formula is C8H11BO3, Safety of 2-Methoxy-5-methylphenylboronic acid.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Hansen, Anders Lindhardt published the artcileFast and regioselective Heck couplings with N-acyl-N-vinylamine derivatives, Application In Synthesis of 16332-06-2, the main research area is vinyl amide derivative aryl triflate Heck coupling; aryl methyl ketone preparation; arylvinyl amide preparation; arylethyl amide preparation.

Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved in good yields using catalytic amounts of Pd2(dba)3, DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinyl amides and an example each of an N-vinyl carbamate and an N-vinyl urea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl Me ketone or in situ hydrogenation in the presence of (Ph3P)3RhCl under a hydrogen atm. to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the α-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

Journal of Organic Chemistry published new progress about Heck reaction. 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Application In Synthesis of 16332-06-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Mantel, Mette L. H. published the artcilePd-catalyzed C-N bond formation with heteroaromatic tosylates, Computed Properties of 16332-06-2, the main research area is heteroaryl amide preparation; amide heteroaryl tosylate arylation palladium.

A protocol for the palladium(0)-catalyzed amidation of heteroaromatic tosylates was successfully developed. The methodol. proved to be effective for a variety of heteroaryl tosylates including the pyridine, pyrimidine, quinoline and quinoxaline ring systems. Successful carbon-nitrogen bond formation with these heteroaryl tosylates could be performed with a wide range of primary amides, oxazolidinones, lactams, anilines and indoles, including one cyclic urea. Moreover, this C-N bond forming reaction provided products with high structural diversity. The coupling reaction was also amenable to scale up applications.

Chemistry – A European Journal published new progress about Arylation. 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Computed Properties of 16332-06-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Khalaf, Juhienah published the artcileDesign, Synthesis, and Diversification of 3,5-Substituted Enone Library, Quality Control of 127972-00-3, the main research area is enone combinatorial library preparation; bromoenone preparation boronic acid Suzuki coupling; terminal alkyne bromoenone Sonogashira coupling; triazole preparation.

This paper describes the synthesis of a 300 member library of 3,5-substituted enones, e.g., I. The synthesis starts with six different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Addnl. a small series of triazoles, e.g., II, were synthesized by a Sonogashira coupling reaction dipolar cycloaddition sequence. The library was analyzed by principal component anal. to examine its diversity.

ACS Combinatorial Science published new progress about Alkynes, α- Role: RCT (Reactant), RACT (Reactant or Reagent). 127972-00-3 belongs to class ethers-buliding-blocks, name is 2-Methoxy-5-methylphenylboronic acid, and the molecular formula is C8H11BO3, Quality Control of 127972-00-3.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Hameury, Sophie published the artcileBis(ether-functionalized NHC) Nickel(II) Complexes, Trans to Cis Isomerization Triggered by Water Coordination, and Catalytic Ethylene Oligomerization, SDS of cas: 622-86-6, the main research area is crystal structure imidazolylidene nickel preparation conformer oligomerization catalyst ethylene; mol structure imidazolylidene nickel preparation conformer oligomerization catalyst ethylene.

The new Ni(II) complexes containing NHC ligands N-substituted by a CH2CH2OR ether group (R = Me or Ph) [NiCl2{ImMes(C2OMe)}2] (6, Im = C3H2N2; Mes = mesityl; C2OMe = CH2CH2OMe), [NiCl2{ImBu(C2OMe)}2] (7), [NiBr2{ImDiPP(C2OMe)}2] (8, Dipp = 2,6-diisopropylphenyl), [NiBr2{ImMes(C2OMe)}2] (9), [NiBr2{ImBu(C2OMe)}2] (10), [NiBr2{ImMes(C2OPh)}2] (18; C2OPh = CH2CH2OPh), [NiI2{ImDiPP(C2OMe)}2] (21), [NiI2{ImMes(C2OMe)}2] (22), and [NiI2{ImBu(C2OMe)}2] (23) were synthesized in good yields and fully characterized by NMR spectroscopy and x-ray diffraction anal. The reaction conditions were optimized and further applied to thioether or nonfunctionalized NHC ligands, affording [NiBr2{ImDiPP(C2SPh)}2] (19, C2SPh = CH2CH2SPh) and [NiBr2{ImDiPPBu}2] (20), resp. Equilibrium involving syn/anti isomers were unveiled for complexes [NiCl2{ImDiPP(C2OMe)}2] (5), 6-10, and 18-23. Reactions of 6 and 20 with a halide abstractor afforded the dicationic aquo complexes cis-[Ni{ImMes(C2OMe)}2(H2O)2][PF6]2 (27) and cis-[Ni{ImDiPPBu}2(H2O)2][PF6]2 (28), in which a cis arrangement of the carbene ligands is evidenced, which contrasts with that in their precursors. These mols. represent rare examples of Ni aquo NHC complexes and of complexes with two cis monodentate NHC ligands. The new complexes reported in this work (15 crystal structures) displayed moderate activities as precatalysts for ethylene oligomerization and favored dimerization.

Organometallics published new progress about Aluminoxanes, Me Role: CAT (Catalyst Use), USES (Uses). 622-86-6 belongs to class ethers-buliding-blocks, name is (2-Chloroethoxy)benzene, and the molecular formula is C8H9ClO, SDS of cas: 622-86-6.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Di Franco, Thomas published the artcileSynthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes, Category: ethers-buliding-blocks, the main research area is alkene preparation; alkyl halide alkenylborabicyclononane Suzuki Miyaura coupling Ni catalyst.

The first Ni-catalyzed Suzuki-Miyaura coupling of alkyl halides with alkenyl-(9-BBN) reagents is reported. Both primary and secondary alkyl halides including alkyl chlorides can be coupled. The coupling method can be combined with hydroboration of terminal alkynes, allowing the expedited synthesis of functionalized alkyl alkenes from readily available alkynes with complete (E)-selectivity in one pot. The method was applied to the total synthesis of (±)-Recifeiolide, a natural macrolide.

Organic Letters published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 622-86-6 belongs to class ethers-buliding-blocks, name is (2-Chloroethoxy)benzene, and the molecular formula is C8H9ClO, Category: ethers-buliding-blocks.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Palvoelgyi, Adam Mark published the artcileCounterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids, Product Details of C11H16O2, the main research area is aldehyde allyl alc palladium phosphoric acid amine chiral allylation; enal stereoselective preparation.

We report a straightforward and efficient Pd/enamine catalytic procedure for the direct asym. α-allylation of branched aldehydes. The use of simple chiral amines and easily prepared achiral or racemic phosphoric acids, together with a suitable Pd-source resulted in a highly active and enantioselective catalyst system for the allylation of various α-branched aldehydes with different allylic alcs. The reported procedure could provide an easy access to both product antipodes. Furthermore, two possible orthogonal derivatizations of the enantioenriched aldehydes were performed without any decrease in enantioselectivity.

Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 121-00-6 belongs to class ethers-buliding-blocks, name is 4-Hydroxy-3-tert-butylanisole, and the molecular formula is C11H16O2, Product Details of C11H16O2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

De Smet, Gilles published the artcileSelective Nickel-Catalyzed Hydrodeacetoxylation of Aryl Acetates, Related Products of ethers-buliding-blocks, the main research area is aromatic alc magnesium catalyst acetoxylation; aryl acetate preparation nickel catalyst chemoselective hydrodeacetoxylation green chem; anisole preparation; Aryl Acetates; C−O Bond Activation; Hydrodeacetoxylation; Nickel Catalysis; Renewable Resources.

Ni-catalyzed hydrodeacetoxylation of aryl acetates (Ar-OAc) with HBpin in a green carbonate solvent selectively delivered the corresponding deoxygenated arenes (ArH). The method was also applicable to highly challenging guaiacyl and syringyl acetates, leaving -OMe groups intact without arene reduction Renewable 4-propylguaiacol obtained from pine could also be transformed without significant loss in yield vs. oil derived feedstock. The observed chemoselectivity for Ar-OAc vs. ArO-Ac bond cleavage was rationalized based on mechanistic experiments and DFT calculations ArOH side-product formation was attributed to direct competitive Ni-catalyzed reduction of the C=O bond. Hydrodeacyloxylation of a set of aryl alkanoates featured interesting chemoselectivity with a dramatic influence of the length and structure of the alkyl chain on catalysis.

Angewandte Chemie, International Edition published new progress about Aromatic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 121-00-6 belongs to class ethers-buliding-blocks, name is 4-Hydroxy-3-tert-butylanisole, and the molecular formula is C11H16O2, Related Products of ethers-buliding-blocks.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Li, Longjia published the artcileAmphiphilic ligands for Cu-catalyzed aerobic oxidation to synthesize 9-fluorenones in water, Related Products of ethers-buliding-blocks, the main research area is fluorenone preparation; fluorene aerobic oxidation copper catalyst.

A series of amphiphilic PEG-functionalized nitrogen ligands were developed for the highly efficient copper-catalyzed aerobic oxidation of 9-fluorenes, with mol. oxygen as the sole oxidant in neat water to afford 9-fluorenones I [R = H, 2-NH2, 2-I, etc.]. A broad range of functional groups were well tolerated and thus offered the opportunity for further functionalization.

Catalysis Communications published new progress about Oxidation. 23783-42-8 belongs to class ethers-buliding-blocks, name is 2,5,8,11-Tetraoxatridecan-13-ol, and the molecular formula is C9H20O5, Related Products of ethers-buliding-blocks.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Mao, Wuyu published the artcileOrganocatalytic and Scalable Syntheses of Unsymmetrical 1,2,4,5-Tetrazines by Thiol-Containing Promotors, Synthetic Route of 23783-42-8, the main research area is tetrazine derivative preparation; nitrile heterocyclization olefination; annulations; heterocycles; nitriles; organocatalysis; synthetic methods.

Despite the growing application of tetrazine bioorthogonal chem., it is still challenging to access tetrazines conveniently from easily available materials. Described here is the de novo formation of tetrazine from nitriles and hydrazine hydrate using a broad array of thiol-containing catalysts, including peptides. Using this facile methodol., the syntheses of 14 unsym. tetrazines, containing a range of reactive functional groups, on the gram scale were achieved with satisfactory yields. Using tetrazine methylphosphonate as a building block, a highly efficient Horner-Wadsworth-Emmons reaction was developed for further derivatization under mild reaction conditions. Tetrazine probes with diverse functions can be scalably produced in yields of 87-93 %. This methodol. may facilitate the widespread application of tetrazine bioorthogonal chem.

Angewandte Chemie, International Edition published new progress about Heterocyclization. 23783-42-8 belongs to class ethers-buliding-blocks, name is 2,5,8,11-Tetraoxatridecan-13-ol, and the molecular formula is C9H20O5, Synthetic Route of 23783-42-8.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem