Tag: M.W=100-150

Jones, Roderick C. published the artcileControlling reactivity in the Fujiwara-Moritani reaction: Examining solvent effects and the addition of 1,3-dicarbonyl ligands on the oxidative coupling of electron rich arenes and acrylates, Computed Properties of 151-10-0, the main research area is Fujiwara Moritani dicarbonyl ligand oxidative coupling arene acrylate solvent.

A palladium-catalyzed direct alkenylation of electron rich arenes in the presence of K2S2O8 with an acetic acid/1,4-dioxane solvent combination was developed. The 1,4-dioxane co-solvent dramatically influences the rate of reaction, giving selectively disubstituted alkenes, while the addition of acetylacetone ligands increases site selectivity for the alkenylation of monofunctionalized arenes. The participation of these carbonyl ligands was confirmed by ESI-MS studies, with some key in situ intermediates in the catalytic cycle identified. A variety of electron rich arenes and olefinic substrates can be used in the direct oxidative coupling to give disubstituted alkenes in moderate to good yields.

Tetrahedron Letters published new progress about 1,3-Dicarbonyl compounds Role: CAT (Catalyst Use), USES (Uses). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Computed Properties of 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Liu, Xiong published the artcileFullerotetrahydroquinolines: TfOH/TsOH · H2O-Mediated One-Pot Two-Step Synthesis and N-Alkylation/Acylation/Carboamidation Reaction, Synthetic Route of 5961-59-1, the main research area is fullerene amine paraformaldehyde alkylation acylation carboamidation toluenesulfonic trifluoromethanesulfonic acid; fullerotetrahydroquinoline one pot preparation.

A series of N-unsubstituted/substituted fullerotetrahydroquinolines without a directly attached nitrogen atom were synthesized in moderate to good yields via a one-pot two-step reaction of [60]fullerene with arylamines and paraformaldehyde in the presence of trifluoromethanesulfonic acid and p-toluenesulfonic acid monohydrate. Aromatic primary amines produce N-unsubstituted fullereotetrahydroquinolines, while aromatic secondary amines give N-substituted fullereotetrahydroquinoline derivatives As precursors, N-unsubstituted fullerotetrahydroquinolines could be further derivatized by the N-alkylation/acylation/carboamidation reactions to produce a large variety of N-substituted fullerotetrahydroquinolines containing Cl, NO2, C(O), and C(O)NH functional groups, which may have applications in the field of perovskite-based solar cells. Plausible reaction pathways for the formation of N-unsubstituted/substituted fullerotetrahydroquinolines were suggested to elucidate the above-mentioned reaction process.

Advanced Synthesis & Catalysis published new progress about Acetophenones Role: RCT (Reactant), RACT (Reactant or Reagent). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Synthetic Route of 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Harenberg, Johannes H. published the artcilePreparation of Functionalized Aryl, Heteroaryl, and Benzylic Potassium Organometallics Using Potassium Diisopropylamide in Continuous Flow, Name: 1,3-Dimethoxybenzene, the main research area is metalation continuous flow generation organopotassium aromatic hetaryl nucleophile; electrophile addition coupling organopotassium aromatic heterocyclic compound; alc ketone thioether silane preparation organopotassium nucleophile addition coupling; arenes; flow chemistry; heteroarenes; lateral metalation; potassium.

Heterocyclic and aromatic compounds were metalated by lithium-free potassium diisopropylamide serving as nucleophiles in carbonyl group addition and coupling reactions, providing access to versatile substituted benzothiazoles, benzothiophenes, benzofurans and functionalized aromatic compounds We report the preparation of lithium-salt-free KDA (potassium diisopropylamide; 0.6 M in hexane) complexed with TMEDA (N,N,N’,N’-tetramethylethylenediamine) and its use for the flow-metalation of (hetero)arenes between -78° and 25° with reaction times between 0.2 s and 24 s and a combined flow rate of 10 mL min-1 using a com. flow setup. The resulting potassium organometallics react instantaneously with various electrophiles, such as ketones, aldehydes, alkyl and allylic halides, disulfides, Weinreb amides, and Me3SiCl, affording functionalized (hetero)arenes in high yields. This flow procedure is successfully extended to the lateral metalation of methyl-substituted arenes and heteroaromatics, resulting in the formation of various benzylic potassium organometallics. A metalation scale-up was possible without further optimization.

Angewandte Chemie, International Edition published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Name: 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kawano, Teruhiro published the artcileCatalytic Hydrogenation of Carboxamides with a Bifunctional Cp*Ru Catalyst Bearing an Imidazol-2-ylidene with a Protic Aminoethyl Side Chain, COA of Formula: C8H11NO, the main research area is amine preparation; carboxamide hydrogenation ruthenium catalyst.

Synthesis of a Cp*Ru complex bearing an NH2-functionalized N-heterocyclic carbene (C-NH) I (R = CH3) was achieved by treatment of Cp*RuBr(isoprene) with an equimolar amount of a silver complex, which was generated from Ag2O and 1-(2-aminoethyl)-3-methylimidazolium bromide, in CH3CN at room temperature The new Cp*RuBr(C-NH) complex I showed a higher catalytic performance than the related Cp*RuCl(P-NH) and Cp*RuCl(N-NH) complexes. In the reaction of N-arylcarboxamides R1C(O)NR2R3 (R1 = H, C6H5, pyridin-3-yl; R2 = R3 = CH3; R2 = H, R3 = C6H5; R2R3 = -C(O)(CH2)3-, etc.), the amine products R2R3NH were obtained in satisfactory yields under mild temperature conditions.

Synthesis published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, COA of Formula: C8H11NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Calogero, Francesco published the artcileDiastereoselective and enantioselective photoredox pinacol coupling promoted by titanium complexes with a red-absorbing organic dye, Safety of 1,3-Dimethoxybenzene, the main research area is aryl aldehyde enantioselective diastereoselective photoredox pinacol coupling; bis aryl ethane diol preparation.

A highly diastereoselective pinacol coupling reaction of aromatic aldehydes promoted by 5 mol% of the non-toxic, inexpensive and available Cp2TiCl2 complex. The key feature that allowed the complete control of diastereoselectivity was the employment of a red-absorbing organic dye in the presence of a redox-active titanium complex. Taking advantage of the well-tailored photoredox potential of this organic dye, the selective reduction of Ti(IV) to Ti(III) was achieved. These conditions enable the formation of the D,L (syn) diastereoisomer as the favored product of the pinacol coupling (d.r. > 20 : 1 in most of the cases). Moreover, employing a simply prepared chiral SalenTi complex, the new photoredox reaction gave a complete diastereoselection for the D,L diastereoisomer and high enantiocontrol (up to 92% of enantiomeric excess).

Chemical Science published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Safety of 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Bryant, Dillon J. published the artcileSynthesis and Study of a Dialkylbiaryl Phosphine Ligand; Lessons for Rational Ligand Design, SDS of cas: 151-10-0, the main research area is methylphosphinedimethoxybiphenyl ligand preparation catalyst palladium cross coupling aryl chloride; crystal structure methylphosphinedimethoxybiphenyl ligand palladium complex; mol structure methylphosphinedimethoxybiphenyl ligand palladium complex.

The rational design and synthesis of a novel dialkylbiarylphosphine ligand, 2′-(dimethylphosphine)-2,6-dimethoxy-1,1′-biphenyl (MeSPhos), for Pd-catalyzed C-N cross-coupling reactions is described. Based on previous results, it was hypothesized that a ligand with electronic properties similar to (2-biphenyl)dimethylphosphine (MeJPhos) but with greater steric bulk would allow the cross-coupling of previously inaccessible deactivated aryl chlorides. As predicted, MeSPhos exhibited similar electronic properties to MeJPhos. However, MeSPhos surprisingly showed a significantly smaller steric profile than MeJPhos. In comparison to the widely used CySPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl), MeSPhos promoted the oxidative addition of highly deactivated aryl chlorides for which CySPhos was ineffective, but significantly decreased the rate of reductive elimination. The kinetics of cross-coupling reactions showed that the altered steric and electronic parameters of MeSPhos had a significant impact on the rate of cross-coupling, and the decreased steric bulk had a profound deleterious impact on the catalyst stability. With regard to this latter point, only the most activated aryl chlorides reacted at a sufficient rate to overcome the rate of catalyst decomposition The relation between the electron-donating ability of the phosphine ligand and the rate of oxidative addition is complex, and they also illustrate that increasing substitution on the biphenyl structure does not necessarily increase the steric bulk of the ligand.

Organometallics published new progress about Aryl chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, SDS of cas: 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kasama, Kengo published the artcileEnantiodivergent Synthesis of Axially Chiral Biphenyls from σ-Symmetric 1,1′-Biphenyl-2,6-diol Derivatives by Single Lipase-Catalyzed Acylative and Hydrolytic Desymmetrization, Quality Control of 151-10-0, the main research area is axially chiral biphenyl enantiodivergent preparation biphenyldiol lipase catalyst desymmetrization.

The enzymic acylative desymmetrization of σ-sym. 2′-halo-1,1′-biphenyl-2,6-diols was achieved for the first time using com. available Burkholderia cepacia lipase immobilized on diatomaceous earth to give (S)-mono esters. The hydrolytic desymmetrization of the corresponding diacetates was also achieved using the same lipase to give (R)-mono esters. The authors’ results, therefore, demonstrate that a single lipase can conduct the enantiodivergent synthesis of axially chiral biphenyl compounds in high chem. and optical yields.

European Journal of Organic Chemistry published new progress about Biphenyls Role: SPN (Synthetic Preparation), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Quality Control of 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Murata, Takumi published the artcileSynthesis of silyl formates, formamides, and aldehydes via solvent-free organocatalytic hydrosilylation of CO2, SDS of cas: 5961-59-1, the main research area is silyl formate formamide aldehyde preparation green chem; organocatalytic hydrosilylation carbon dioxide tetrabutylammonium acetate catalyst green.

Carbon dioxide (CO2) was used as a C1 source to prepare silyl formates, formamides, and aldehydes. Tetrabutylammonium acetate (TBAA) catalyzed the solvent-free N-formylation of amines with CO2 and hydrosilane to give formamides including Weinreb formamide, Me(MeO)NCHO, which was successively converted into aldehydes by one-pot reactions with Grignard reagents.

Chemical Communications (Cambridge, United Kingdom) published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, SDS of cas: 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xu, Fan published the artcileA general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C, Product Details of C8H10O2, the main research area is indoxyl preparation; indole nucleophile coupling; brevianamide A trigonoliimine C total synthesis.

The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds Herein, a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxyls via nucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps) is reported. The developed method is operationally simple and demonstrates broad scope in terms of nucleophile identity and indole substitution, tolerating 2-alkyl substituents and free indole N-H groups, elements beyond the scope of most prior approaches. Spirocyclic indoxyl products are also accessible via intramol. nucleophilic trapping.

Chemical Science published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Product Details of C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Boon, Byron A. published the artcileTriarylaminium Radical Cation Promoted Coupling of Catharanthine with Vindoline: Diastereospecific Synthesis of Anhydrovinblastine and Reaction Scope, Application of 1,3-Dimethoxybenzene, the main research area is anhydrovinblastine diastereoselective synthesis oxidative coupling triarylaminium promoted.

A new triarylaminium radical cation promoted coupling of catharanthine with vindoline is disclosed, enlisting tris(4-bromophenyl)aminium hexachlororantimonate (BAHA, 1.1 equiv) in aqueous 0.05 N HCl/trifluoroethanol (1-10:1) at room temperature (25°C), that provides anhydrovinblastine in superb yield (85%) with complete control of the newly formed quaternary C16′ stereochem. A definition of the scope of aromatic substrates that participate with catharanthine in the BAHA-mediated diastereoselective coupling reaction and simplified indole substrates other than catharanthine that participate in the reaction are disclosed that identify the key structural features required for participation in the reaction, providing a generalized indole functionalization reaction that bears little structural relationship to catharanthine or vindoline.

Journal of the American Chemical Society published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Application of 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem