Category: 3893-18-3

Sharma, Mukesh; Das, Biraj; Baruah, Manash J.; Biswas, Subir; Roy, Subhasish; Hazarika, Anil; Bhargava, Suresh K.; Bania, Kusum K. published the artcile< Pd-Au-Y as Efficient Catalyst for C-C Coupling Reactions, Benzylic C-H Bond Activation, and Oxidation of Ethanol for Synthesis of Cinnamaldehydes>, Name: 3-(4-Bromophenyl)acrylaldehyde, the main research area is phenylboronic acid aryl chloride palladium gold nanocatalyst Suzuki Miyaura; biaryl one pot preparation; benzylic alc chloride palladium gold nanocatalyst oxidation; benzaldehyde preparation; acetaldehyde benzaldehyde chloride palladium gold nanocatalyst aldol condensation; cinnamaldehyde preparation.

Pd-Au nanoalloy supported on zeolite-Y (Pd-Au-Y) matrix was found to be an effective catalyst for C-Cl bond activation and oxidative coupling of 2-naphthol, leading to the formation of various biaryl products and 1,1′-bi-2-naphthol, BINOL. The same catalyst was also highly efficient for selective oxidation of benzylic alcs. to benzaldehydes. Cinnamaldehydes were obtained directly from benzaldehydes by aldol condensation with acetaldehyde generated in situ by partial oxidation of ethanol in the presence of Pd-Au-Y catalyst at 120 °C under basic condition. The biaryl products were also obtained directly from benzylic alcs. in a one-pot system by reacting with phenylboronic acid. The formation of biaryls from benzylic alcs. was believed to occur via one-pot benzylic C-H and C-Cl bond activation. A high % yield of biaryls, BINOL, aldehydes, and cinnamaldehydes was obtained by performing different reactions using the single Pd-Au-Y catalyst. The strong interaction of chloro-benzylic alc. was predominantly located at active gold species. X-ray photoelectron and diffuse reflectance spectroscopic studies revealed the strong interaction between Pd and Au particles. Electrochem. studies provided proper evidence for the individual role of the nanoparticles (NPs) in one-pot synthesis of biaryls from benzylic alcs.

ACS Catalysis published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Name: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Lei; Li, Sun; Chauhan, Pankaj; Hack, Daniel; Philipps, Arne R.; Puttreddy, Rakesh; Rissanen, Kari; Raabe, Gerhard; Enders, Dieter published the artcile< Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions>, Computed Properties of 3893-18-3, the main research area is pyrazolone enal NHC chiral aldol condensation annulation catalyst; spiropyrazolone stereoselective preparation; diketone cyclic enal NHC chiral aldol condensation annulation catalyst; chromenedione stereoselective preparation; N-heterocyclic carbene; asymmetric synthesis; chromenedione; multicomponent reaction; spiropyrazolone.

A novel one-pot, three-component diastereo- and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate α,β-unsaturated pyrazolones, which react with a second equivalent of enal through an N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation. The desired spirocyclopentane pyrazolones I (R = Ph, 4-MeOC6H4, 2-MeOC6H4, 4-ClC6H4, 4-BrC6H4, 2-furanyl, 3-thienyl, etc.; R1 = t-Bu, Et, 4-MeOC6H4, 2-naphthyl; R2 = Ph, 4-MeOC6H4, 4-BrC6H4, Bn, t-Bu, etc.) are obtained in moderate to good yields and good to excellent stereoselectivities. Alternatively, starting from cyclic 1,3-diketones, 2,5-chromenediones II (R = Ph, 4-MeOC6H4, 4-MeC6H4, 4-ClC6H4, 2-MeOC6H4, etc.; R1= R2= Me, H; R1= H, R2= Ph) are available through [2+4] annulation.

Chemistry – A European Journal published new progress about Aldol condensation. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Computed Properties of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wu, Xiaoyu; Nie, Linlin; Fang, Huihui; Chen, Jie; Cao, Weiguo; Zhao, Gang published the artcile< Organocatalyzed Cascade Reactions of Cyclic β-Enamino Esters and α,β-Unsaturated Aldehydes Leading to Indoloquinolizidines and Benzoquinolizidines>, Safety of 3-(4-Bromophenyl)acrylaldehyde, the main research area is quinolizidine fused preparation; indoloquinolizidine preparation; benzoquinolizidine preparation; organocatalyst cascade reaction cyclic enamino ester unsaturated aldehyde.

Organocatalyzed cascade reactions between cyclic β-enamino esters and α,β-unsaturated aldehydes have been developed. They provide highly substituted indolo[2,3-a]quinolizidines and benzo[a]quinolizidines in moderate to good yields and with good to excellent enantioselectivities. Both aromatic and aliphatic α,β-unsaturated aldehydes react readily with enamino esters to furnish the desired products. E.g., organocatalyzed reaction of enamino ester (I) with 4-BrC6H4CH:CHCHO gave 77% indolo[2,3-a]quinolizidine (II).

European Journal of Organic Chemistry published new progress about Cyclization (cyclic β-enamino esters). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Safety of 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Yao-Zong; Zhang, Jie; Xu, Peng-Fei; Luo, Yong-Chun published the artcile< Organocatalytic Asymmetric Michael Addition of 1-Acetylindolin-3-ones to α,β-Unsaturated Aldehydes: Synthesis of 2-Substituted Indolin-3-ones>, COA of Formula: C9H7BrO, the main research area is indolinone enantioselective preparation; acetylindolinone unsaturated aldehyde asym Michael addition diarylprolinol trimethylsilylether catalyst.

A highly efficient asym. Michael addition of 1-acetylindolin-3-ones to α,β-unsaturated aldehydes is developed to afford 2-substituted indolin-3-one derivatives, e.g., I, in high yields (up to 94%) with good stereoselectivities (up to 11:1 dr and 96% ee). The Michael adducts can be transformed into substituted cyclopentyl[b]indoline compounds conveniently without racemization.

Journal of Organic Chemistry published new progress about Enantioselective synthesis. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, COA of Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Cho, Kyoungil; Yoo, Jin; Noh, Hyeong-Wan; Lee, Sang Moon; Kim, Hae Jin; Ko, Yoon-Joo; Jang, Hye-Young; Son, Seung Uk published the artcile< Hollow structural effect of microporous organocatalytic polymers with pyrrolidines: dramatic enhancement of catalytic performance>, Computed Properties of 3893-18-3, the main research area is organocatalytic microporous organic polymer structure cinnamaldehyde nucleophile addition.

Hollow and microporous organic polymers bearing pyrrolidines (H-MOP-P) were prepared by template synthesis and post-synthetic modification. H-MOP-P showed enhanced organocatalytic performance, compared to nonhollow microporous catalysts.

Journal of Materials Chemistry A: Materials for Energy and Sustainability published new progress about Azide-alkyne 1,3-dipolar cycloaddition reaction. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Computed Properties of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Morack, Tobias; Mueck-Lichtenfeld, Christian; Gilmour, Ryan published the artcile< Bioinspired Radical Stetter Reaction: Radical Umpolung Enabled by Ion-Pair Photocatalysis>, Electric Literature of 3893-18-3, the main research area is bioinspired Stetter keto acid aldehyde radical umpolung photocatalysis; Stetter reaction; electrostatic interactions; ion pairs; radicals; umpolung.

A bioinspired, intermol. radical Stetter reaction of α-keto acids and aldehydes is disclosed that is contingent on a formal “”radical umpolung”” concept. Enabled by secondary amine activation, electrostatic recognition ensures that the α-ketocarboxylic acids, which function as latent acyl radicals, are proximal to the in situ generated iminium salts. This photoactive contact ion pair is an electron donor-acceptor (EDA) complex, and undergoes facile single electron transfer (SET) and rapid decarboxylation prior to radical-radical recombination. Importantly, decarbonylation is mitigated by this strategy. The initial computational validation on which the process is predicated matches closely with experiment Synergistic organo- and photocatalysis activation principles finally expands the mechanistic and synthetic scope of the classic Stetter reaction to include α,β-unsaturated aldehydes as acceptors.

Angewandte Chemie, International Edition published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Electric Literature of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhou, Jiadi; Jiang, Xinpeng; Jin, Can; Guo, Zhicheng; Su, Bin; Su, Weike published the artcile< One-Pot L-Proline-Mediated Stereoselective α-C(sp2)-H Fluorination of α,β-Unsaturated Aldehydes through Methoxyfluorination-Elimination>, Application In Synthesis of 3893-18-3, the main research area is fluoro unsaturated alc preparation diastereoselective; unsaturated aldehyde Selectfluor fluorination proline catalyst.

A one-pot, two-step L-proline-mediated stereoselective α-C(sp2)-H fluorination of α,β-unsaturated aldehydes RHC=CHCHO (R = 2-ClC6H4, 2-naphthyl, (CH2)2CH3, etc.) towards their corresponding (Z)-α-fluoro-αβ-unsaturated aldehydes (Z)-RHC=C(F)CHO has been developed. The first step utilizes Selectfluor as a fluorinating agent in CH3NO2/MeOH forming (Z)-α-fluoro-α,β-unsaturated aldehydes and their corresponding di-Me acetals through methoxyfluorination-elimination. In the second step, water is added to promote the hydrolytic cleavage of the di-Me acetals. The obtained (Z)-α-fluoro-α,β-unsaturated aldehydes were smoothly reduced to the corresponding alcs. (Z)-RHC=C(F)CH2OH by using NaBH4.

European Journal of Organic Chemistry published new progress about Alcohols, unsaturated Role: SPN (Synthetic Preparation), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application In Synthesis of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jiang, Zhiwei; Toffano, Martial; Vo-Thanh, Giang; Bournaud, Chloee published the artcile< Bifunctional N-Heterocyclic Carbene-Catalyzed Highly Enantioselective Trans-Cyclopentannulation of Enals and Enones via Homoenolate>, Computed Properties of 3893-18-3, the main research area is cyclopentene preparation enantioselective diastereoselective; enal enone trans cyclopentannulation bifunctional heterocyclic carbene catalyst.

An efficient and flexible synthesis of a new class of chiral bifunctional NHC catalysts I [R = i-Pr, i-Bu, Bn, cyclohexyl; Ar = Ph, 3,5-bis(trifluoromethyl)phenyl, pentafluorophenyl, 2-methoxyphenyl; X = S, O] has been reported. These new imidazolylidene NHCs I, bearing a (thio)urea function as a hydrogen bond donor promoted efficiently highly diastereoselective trans-cyclopentannulation of enals R1CH=CHCHO (R1 = n-Pr, Ph, naphthalen-2-yl, furan-2-yl, etc.) and enones R2CH=CHC(O)R3 (R2 = methoxycarbonyl, Ph, thiophen-2-yl, etc.; R3 = Ph, 2-phenylethenyl, thiophen-2-yl, etc.) in moderate to good yields (up to 69% yield) along with excellent enantioselectivity (up to 96% ee). This methodol. could be applied to a large variety of substrates (30 examples).

ChemCatChem published new progress about Amino alcohols, chiral Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Computed Properties of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Binghao; Qi, Jing; Wu, Yatong; Li, Jia-Hui; Li, Yanting; Duan, Xiao-Yong published the artcile< The N-heterocyclic carbene-catalyzed [3 + 2] annulation of isoindigos with enals: the enantioselective construction of three contiguous stereogenic centers>, COA of Formula: C9H7BrO, the main research area is dimeric spirocyclic bisindoline alkaloid preparation diastereoselective enantioselective; enal isoindigo annulation heterocyclic carbene.

Constructing contiguous all-carbon quaternary stereogenic centers has posed a long-standing synthetic challenge in organic chem. In this work, the NHC-catalyzed enantioselective [3 + 2] annulation of enals with isoindigo was introduced as an efficient strategy for the construction of dimeric spirocyclic bisindoline alkaloid derivatives with moderate yields and good enantioselectivities. Remarkably, three contiguous stereogenic centers-including two congested all-carbon quaternary stereogenic centers-were successfully constructed in a simple one-step operation.

Organic Chemistry Frontiers published new progress about [3+2] Cycloaddition reaction catalysts. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, COA of Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Elguero, Jose; Jacquier, Robert; Marzin, Claude published the artcile< Synthesis of azines from α,β-unsaturated β-(p-bromophenyl) carbonyl compounds>, Formula: C9H7BrO, the main research area is azines alkenyl; cinnamaldehydes azines; phenyl oxoalkenes; alkenones Ph; alkenals Ph.

Reduction of p-BrC6H4Ac with LiAlH4 gave 82% p-BrC6H4CHMeOH, b16 135-6°, which was dehydrated over K pyrosulfate to p-BrC6H4CH:CH2, b15 90°, and converted to p-BrC6H4CH:CHCHO (I), m. 79-80°, by known methods. p-BrC6H4CHO and acetone yielded 30% p-BrC6H4CH:CHAc (II), m. 78-80° (2,4-dinitrophenylhydrazone m. 246-7°), and 15% (p-BrC6H4CH:CH)2CO, m. 205-7° (2,4-dinitrophenylhydrazone m. 225-7°), even with excess acetone. 1-(p-Bromophenyl)-2-methyl-3-chloro-2-propen-1-one, m. 63-5°, with MeOH and NaOH gave 77% mixture containing 65% p-BrC6H4-COCHMeCH(OMe)2 and 35% 1-(p-bromophenyl)-2-methyl-3-methoxy-2-propen-1-one. Reduction of the mixture with LiAlH4 gave, after preparative gas chromatog., p-bromo-α-methylcinnamal-dehyde (III) along with p-bromobenzaldehyde, 3-(p-bromophenyl)-2-methyl-1-penten-3-ol, and 1-(p-bromophenyl)-2-methyl-3,3-dimethoxypropan-1-ol. By the method of Knoepfer (CA 3: 1535), I gave 40% (p-BrC6H4CH:CHCH:N)2, m. 229-31°. II similarly gave 45% (p-BrC6H4CH:CHCMe:N)2, m. 203-5°, and 10% II hydrazone, m. 143-5°. III (0.005 mole), 0.0025 mole N2H4, and a small amount of p-MeC6H4SO3H yielded 85% (p-BrC6H4CH:CMeCH:N)2, m. 189-91°. N.M.R., ir, and uv data for the azines were tabulated.

Bulletin de la Societe Chimique de France published new progress about Azines Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary