Month: October 2022

Choudhuri, Khokan; Maiti, Saikat; Mal, Prasenjit published the artcile< Iodine(III) Enabled Dehydrogenative Aryl C-S Coupling by in situ Generated Sulfenium Ion>, Related Products of 576-83-0, the main research area is diaryl sulfide preparation; thiol arene phenyliodo diacetate dehydrogenative coupling reaction; aryl sulfinyl arene preparation; arene thiol phenyliodo diacetate sulfoxidation.

An umpolung based one pot and direct C-S coupling approach under metal free and mild condition were described. Electrophile sulfenium ions were generated in situ from thiols RSH (R = Ph, Et, 4-nitrophenyl, 3-chlorophenyl, etc.) using iodine(III) reagent PhI(OAc)2 (PIDA) and subsequently used for aromatic electrophilic substitution (EArS) to synthesize diaryl sulfides R1SR (R1 = 2,4,6-trimethylphenyl, 4-methoxyphenyl, 2,4-dimethylphenyl, etc.). Also by using of appropriate amount of PIDA, cascaded synthesis of C-S and S=O bonds led to aryl sulfinyl arenes R1S(O)R in one pot. Covalent self-sorting or competitive experiments further confirmed the involvement of sulfenium ion in the EArS.

Advanced Synthesis & Catalysis published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 576-83-0 belongs to class bromides-buliding-blocks, and the molecular formula is C9H11Br, Related Products of 576-83-0.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Meng; Chen, Jun; Chen, Zongjia; Zhong, Changxu; Lu, Ping published the artcile< Enantioselective Desymmetrization of Cyclobutanones Enabled by Synergistic Palladium/Enamine Catalysis>, Computed Properties of 135999-16-5, the main research area is cyclobutanone enantioselective desymmetrization palladium enamine catalyst; arylation; cyclobutanones; desymmetrization; palladium; synergistic catalysis.

The enantioselective intramol. α-arylation of cyclobutanones was established by combining palladium and enamine catalyst systems. Two different enantioselective control strategies were developed for cyclobutanone substrates bearing O- or N-tethered aryl bromides. Further synthetic applications are also reported.

Angewandte Chemie, International Edition published new progress about Arylation. 135999-16-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2, Computed Properties of 135999-16-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Berger, Martin; Carboni, Davide; Melchiorre, Paolo published the artcile< Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals>, Quality Control of 3893-18-3, the main research area is prenyl enal preparation regioselective chemoselective enantioselective photochem; unsaturated aldehyde allyl silane allylation organocatalyst; allylation; enantioselectivity; organocatalysis; photochemistry; regioselectivity.

Synthesis of first catalytic enantioselective conjugate addition of allyl groups R1R2C=CH-CH2Si(CH3)3 [R1 = i-Pr, Me, cyclohexyl; R2 = i-Pr, cyclohexyl, n-hexyl, Ph; R1R2 = -(CH2)5-, -(CH2)2O(CH2)2-] (I) to α,β-unsaturated aldehydes ArCH=CHCHO (II) (Ar = Ph, 4-chlorophenyl, 3-methylphenyl, etc.) was reported. The chem. exploits the visible-light-excitation of chiral iminium ions to activate allyl silanes I towards the formation of allylic radicals, which are then intercepted stereoselectively. The underlying radical mechanism of this process overcomes the poor regio- and chemoselectivity that traditionally affects the conjugate allylation of enals II proceeding via polar pathways. Synthesis demonstrates that this organocatalytic strategy could selectively install a valuable prenyl fragment at the β-carbon of enals R1R2C=CHCH2CH(Ar)CH2CHO.

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, Quality Control of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Yajun; Jiang, Dandan; Fang, Zheng; Zhu, Ning; Sun, Naixian; He, Wei; Liu, Chengkou; Zhao, Lili; Guo, Kai published the artcile< Photomediated core modification of organic photoredox catalysts in radical addition: mechanism and applications>, Application of C8H8BrF, the main research area is bismethoxyphenyl dihydrophenazine bromoalkane photochem cross coupling; alkyl bisphenyl dihydrophenazine preparation.

Here, a new kind of core modification for dihydrophenazines, phenoxazines and phenothiazines was developed through this cross-coupling process. Mechanistic studies suggested that the radical species would be more likely to couple with OPC’ radical cations rather than the ground-state OPC. Core modification of OPCs could stabilize the radical ions in an oxidative quenching catalytic cycle. Significantly, core modifications of OPCs could lower the energy of light required for photoexcitation. Compared with their noncore-modified counterparts, all the core-modified dihydrophenazines and phenoxazines exhibited efficient performance in controlling O-ATRP for the synthesis of poly(Me methacrylate) with higher initiator efficiencies under the irradiation of simulated sunlight.

Chemical Science published new progress about Atom transfer radical polymerization. 405931-46-6 belongs to class bromides-buliding-blocks, and the molecular formula is C8H8BrF, Application of C8H8BrF.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Barber, E. Ryan; Hynds, Hannah M.; Stephens, Claudia P.; Lemons, Holli E.; Fredrickson, Emily T.; Wilger, Dale J. published the artcile< Nickel-Catalyzed Hydroarylation of Alkynes under Reductive Conditions with Aryl Bromides and Water>, SDS of cas: 2725-82-8, the main research area is nickel catalyzed hydroarylation alkyne aryl bromide; reductive cross coupling alkyne arylbromide water anti selectivity.

An operationally simple nickel-catalyzed hydroarylation reaction for alkynes is described. This three-component coupling reaction utilizes com. available alkynes and aryl bromides, along with water and Zn. An air-stable and easily synthesized Ni(II) precatalyst is the only entity used in the reaction that is not com. available. This reductive cross-coupling reaction displays a fairly unusual anti selectivity when aryl bromides with ortho substituents are used. In addition to optimization data and a preliminary substrate scope, complementary experiments including deuterium labeling studies are used to provide a tentative catalytic mechanism. We believe this report should inspire and inform other Ni-catalyzed carbofunctionalization reactions.

Journal of Organic Chemistry published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 2725-82-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H9Br, SDS of cas: 2725-82-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kamlar, Martin; Franc, Michael; Cisarova, Ivana; Gyepes, Robert; Vesely, Jan published the artcile< Formal [3+2] cycloaddition of vinylcyclopropane azlactones to enals using synergistic catalysis>, Application of C9H7BrO, the main research area is spirocyclic azlactone enantioselective preparation; enal vinylcyclopropane azlactone cyclization palladium complex chiral amine catalyst.

Asym. cyclization of enals with vinylcyclopropane azlactones efficiently catalyzed by the combination of achiral Pd(0) complexes and chiral secondary amines was reported. Corresponding spirocyclic azlactones I [R1 = t-Bu, Ph; R2 = Et, Ph, 4-O2NC6H4, etc.; stereo = (5S,6S,7S,8R)/(5R,6S,7S,8R)] were produced in high yields with moderate diastereoselectivities and excellent enantioselectivities. This protocol provided an efficient and easily-performed route to spirocyclic scaffolds and densely functionalized cyclopentanes containing quaternary carbon centers.

Chemical Communications (Cambridge, United Kingdom) published new progress about [3+2] Cycloaddition reaction, stereoselective. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Bunnett, J. F.; Rauhut, Michael M.; Knutson, David; Bussell, Geo. E. published the artcile< The conditions, scope, and mechanism of the von Richter reaction>, Recommanded Product: 2,3-Dibromobenzoic acid, the main research area is .

Experiments with D compounds showed that in the reaction of p-O2NC6H4Cl (I) with alc. KCN to form m-ClC6H4CO2H (II), and in the transformation of PhNO2 to BzOH, H exchange with the solvent occurred. Efforts to isolate a nitrile intermediate have been unsuccessful, but it is shown that nitriles are hydrolyzed rapidly under the conditions of the reaction. Br2C6H3NO2 (III) having Br ortho to the NO2 group reacted poorly, but III with unflanked NO2 groups gave fair yields. A tarry, amorphous byproduct was shown to contain CO2H groups. The optimum conditions for the reaction have been defined and the mechanism is discussed. 2,6-Br2C6H3NH2 diazotized in 9.5M HCl below 0°, and the diazonium cobaltinitrite prepared and decomposed by the method of Hodgson and Marsden (C.A. 38, 2021.8) gave 22% 2,6-III m. 81-3°. m-BrC6H4NHAc nitrated by the method of Case and Sloviter (C.A. 32, 529.9), the resulting mixed products deacetylated by acid hydrolysis, the crude mixed anilines diazotized, and the diazonium salts treated with CuBr gave 2,4-III. 3,5-III, m. 105-6°, was prepared by the method of Shepherd (C.A. 41, 4465h). The nitration of p-C6H4Br2, m. 87°, gave 2,5-III, m. 81-3°. Heating 12.5 g. p-ClC6H4NH2.HCl and 10 g. 99.5% D2O 112 h. at 120° in a sealed tube (or 24 h. at 150°), neutralizing with 6M NaOH, diluting with about 40 cc. dioxane, adding the solution slowly with stirring to a previously prepared mixture of 43 cc. cold concentrated H2SO4 and 50 g. K2S2O8, stirring 1 h. with cooling, pouring onto 300 cc. crushed ice, neutralizing with saturated aqueous Na2CO3, filtering off the light yellow, flocculent material, letting the mixture stand, filtering off a 2nd crop after 1.5 h., dissolving the combined material in 200 cc. glacial AcOH, treating the solution with 200 cc. 30% H2O2, 200 cc. glacial AcOH, and 13 g. HNO3 (d. 1.42), heating the resulting green solution 45 min. on the steam bath, pouring it into 1500 cc. H2O, and recrystallizing the flocculent precipitate from EtOH yielded 6.2 g. D-labeled I (IV), m. 81.5-2.5°, containing 1.02 atoms D/mol. In another run the contents of the sealed tube treated with dilute HCl, diazotized, the diazonium cobaltinitride formed and decomposed in the usual manner, and the product steam distilled and recrystallized from EtOH gave 2.6 g. IV, m. 83-4°, containing 0.99 atom D/mol. B(OEt)3 (10.8 g.) and 5.0 g. D2O kept overnight, and the mixture distilled gave EtOD which was stored in sealed ampuls. A series of von Richter reactions [cf. Ber. 8, 1418(1875)] was carried out by the procedure described previously (C.A. 44, 9938c) with 4.0 g. p-BrC6H4NO2 (V) each under the following conditions (time in hrs., weight of KCN used in g., aqueous solvent, % conversion, and % recovered V given). At 150° in a sealed tube: 1, 2.6, 25 cc. 50% MeOH, 12.5, 55; 1, 10.4, 25 cc. 50% MeOH, 21, 0; 1, 2.6, 25 cc. 48% EtOH, 22, 35; 1, 2.6, 25 cc. 50% PrOH, 11, 55; 1, 2.6, 25 cc. 50% iso-PrOH, 10, 72; 1, 2.6, 25 cc. 50% BuOH, 2.5, 85. At reflux temperature: 48, 8.1, 34 cc. 48% EtOH, 37, 0; 1.5, 15.0, 50 g. 95% pinacol, 1.5, 60; 2.5, 15.0, 75 cc. (HOCH2CH2)2O, 2.5, 0; 2.5, 15.0, 30 cc. 99% BuC(OH)Me2, 0, 65; 2.5, 15.0, 98% AmC(OH)MeBu, 0, 70. PhNO2 (2.5 g.) in 25 cc. 75% aqueous pyridine heated with 2.6 g. KCN 1 h. in a sealed tube at 150° gave only 96% recovered PhNO2. In a similar run in 25 cc. 80% dioxane with 5.0 g. KCN in a sealed tube during 2 h. at 160°, 88% PhNO2 was recovered. PhNO2 (2.5 g.) and 5.0 g. KCN in 25 cc. 48% aqueous EtOH heated 1.5 h. in a sealed tube at 160° yielded 10% BzOH and 12% recovered PhNO2. A series of similar runs was carried out with I (time, weight of I used in g., weight of KCN, aqueous solvent, % conversion, and % recovered I given): Sealed tube at 150°: 50 min. 2.5, 5.0, 25 cc. 48% EtOH, 38, 0. Reflux: 48 h. 3.15, 200.0, 600 cc. 48% EtOH, 42, 0; 18 h. 3.15, 10.3, 75 cc. 48% EtOH, 20, 19; 48 h., 3.15, 20.0, 75 cc. 95% EtOH, 14, 33; 48 h., 3.00, 6.45, 26 cc. 48% EtOH, 40, 0; 48 h., 3.15, 20, 75 cc. 50% MeOH, 20, 0; 48 h., 3.15, 20, 75 cc. 33% MeOH, 15, 6; 48, 3.15, 20, 75 cc. 50% iso-PrOH, 9, 47; 20 h., 3.15, 10.3, 90 cc. 53% EtOH and 22% C6H6, 0, 61; 45 h., 3.15, 20, 75 cc. 50% MeCN, 0, -. Sealed tube at 150°: 1 h., 3.15, 2.6, 75 cc. 50% glycerol-25% EtOH, 0, 79; 1 h., 3.15, 2.6, 75 cc. 50% dioxane, 7, 56. A number of aromatic nitro compounds was submitted to the von Richter reaction; the nitro compound used, the products obtained, % conversion, and % recovered starting material are given for the following reactions in a sealed tube: p-O2NC6H4I, m-IC6H4CO2H (m. 182-3°), 40, 0; 3,5-Cl2C6H3NO2 (m. 63.8-4.2°), 2,4-Cl2C6H3CO2H (m. 158.5-9.5°), 30, 0; m-O2NC6H4F, no acid, 0, 74; p-O2NC6H4F (m. 57-9°), no acid, 0, 14 (the recovered starting material was converted to p-FC6H4CONHPh, m. 182-4°, for identification); p-C6H4(NO2)2, no acid, 0, 6; 2,3-III (m. 85°), 3,4-Br2C6H3CO2H (m. 225-7°), 1, 0 (at reflux); 3,4-III (m. 56-8°), 2,3-Br2C6H3CO2H (m. 144-8°), 16, 0; 2,6-III, no acid, 0, 93; 2,4-III, 3,5-Br2C6H3CO2H (m. 219-20°), 2, 0 (amide, m. 184-6°) (reflux); 3,5-III, 2,4-Br2C6H3CO2H (m. 163-9°), 18, 32 (amide, m. 195-6°); 2,5-III, 2,5-Br2C6H3CO2H (m. 151-3°), 7, 23; 2-O2NC6H4Br, m-BrC6H4CO2H (m. 151-3°), 2, 44 (reflux). PhNO heated 1 h. at 155° with 2.6 g. KCN in 25 cc. 48% EtOH yielded 0.3 g. (PhN:)2, m. 65-6°, which was reduced with Sn and HCl to benzidine, m. 117-20°; in similar runs in 75% dioxane, azoxybenzene, m. 29-31°, was obtained. PhNO2 (5.0 g.), 5.0 g. anhydrous KCN, 5 cc. EtOD, and 5 cc. D2O heated 1 h. in a sealed tube at 150-60° gave 3 g. PhNO2 and 0.380 g. BzOH, m. 120.5-21° (from H2O); the BzOH obtained contained, after equilibration of its CO2H H atoms with H2O, 0.72 atom D/mol. The recovered PhNO2 was nearly D-free. Thus, H atoms from the solvent do become attached to aromatic C during the von Richter reaction. IV (2.2 g.) (containing 1.02 atom D/mol.), 5 g. KCN, and 30 cc. 48% EtOH heated 75 min. at 160-70° in a sealed tube gave II containing 0.42 atom D/mol. IV (containing 0.99 atom D/mol.) gave similarly II containing 0.38 atom D/mol.

Journal of the American Chemical Society published new progress about Intermediates. 603-78-1 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4Br2O2, Recommanded Product: 2,3-Dibromobenzoic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Trofymchuk, Serhii; Bugera, Maksym Ya.; Klipkov, Anton A.; Razhyk, Bohdan; Semenov, Sergey; Tarasenko, Karen; Starova, Viktoriia S.; Zaporozhets, Olga A.; Tananaiko, Oksana Yu.; Alekseenko, Anatoliy N.; Pustovit, Yurii; Kiriakov, Oleksandr; Gerus, Igor I.; Tolmachev, Andrei A.; Mykhailiuk, Pavel K. published the artcile< Deoxofluorination of (Hetero)aromatic Acids>, HPLC of Formula: 16426-64-5, the main research area is deoxofluorination cinnamic carboxylic acid sulfur tetrafluoride safety.

Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines – valuable building blocks for medicinal chem. and agrochem. Of note, sulfur tetrafluoride (SF4) and hydrogen fluoride (HF) are toxic, therefore, safety and addnl. tech. training must be taken before working with them.

Journal of Organic Chemistry published new progress about Aliphatic amines Role: SPN (Synthetic Preparation), PREP (Preparation) (fluorinated). 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, HPLC of Formula: 16426-64-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tanaka, Yuta; Kurasawa, Osamu; Yokota, Akihiro; Klein, Michael G.; Saito, Bunnai; Matsumoto, Shigemitsu; Okaniwa, Masanori; Ambrus-Aikelin, Geza; Uchiyama, Noriko; Morishita, Daisuke; Kimura, Hiromichi; Imamura, Shinichi published the artcile< New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase>, HPLC of Formula: 337536-14-8, the main research area is allosteric deoxyhypusine synthase inhibitor preparation pharmacokinetics SAR.

In this work, a new chem. series possessing fused ring scaffolds designed from high-throughput screening hit compounds was synthesized, discovering a 5,6-dihydrothieno[2,3-c]pyridine derivative I [R = (R)-i-Bu] with potent inhibitory activity. Furthermore, the X-ray crystallog. anal. of the DHPS complex with I [R = (R)-i-Bu] demonstrated a distinct allosteric binding mode compared to a previously reported inhibitor. These findings could be significantly useful in the functional anal. of conformational changes in DHPS as well as the structure-based design of allosteric inhibitors.

ACS Medicinal Chemistry Letters published new progress about Allosteric modulators. 337536-14-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8Br2O2, HPLC of Formula: 337536-14-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary