Month: October 2022

Jayasundara, Chathurika R. K.; Gil-Negrete, Jose M.; Montero Bastidas, Jose R.; Chhabra, Arzoo; Martinez, M. Montserrat; Perez Sestelo, Jose; Smith, Milton R. III; Maleczka, Robert E. Jr. published the artcile< Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents>, Electric Literature of 401-78-5, the main research area is aryl halide iridium catalyzed borylation palladium cross coupling organoindium; borylated alkynyl heteroaryl arene preparation; organoindium palladium catalyzed cross coupling boryl arene.

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective Pd-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodol. The sequential double catalyzed procedure can be also performed in one vessel.

Journal of Organic Chemistry published new progress about Aryl halides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Electric Literature of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mohammadi, Masoud; Ghorbani-Choghamarani, Arash published the artcile< L-Methionine-Pd complex supported on hercynite as a highly efficient and reusable nanocatalyst for C-C cross-coupling reactions>, Quality Control of 401-78-5, the main research area is hercynite magnetic nanocatalyst preparation green chem Suzuki Heck coupling.

A ”green” method was suggested for the synthesis of hercynite magnetic nanoparticles (MNPs) as a novel heterogeneous catalytic support to immobilize homogeneous complexes, L-Methionine-Pd was immobilized on the surface of hercynite MNPs by a simple, rapid, and convenient route. The structure and composition of the prepared Hercynite@L-Methionine-Pd MNPs were characterized by X-ray diffraction spectroscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, SEM, X-ray mapping, thermogravimetric anal. and vibrating-sample magnetometry (VSM). Besides, they were applied as green nanocatalysts for Suzuki and Heck cross-coupling reactions. Hercynite@L-Methionine-Pd MNPs offer several advantages (simple synthetic method under green conditions, thermal and chem. stability during organic reactions, short reaction times, high yields of products, excellent selectivity and easy work-up procedure). Moreover, the recycled nanocatalyst was reused for at least five cycles with no significant loss of activity. The hot filtration test indicated heterogeneous catalysis for Suzuki and Heck cross-coupling reactions. This work is useful for the development and application of a magnetically recoverable Pd nanocatalyst on the basis of green-chem. principles.

New Journal of Chemistry published new progress about Biphenyls Role: SPN (Synthetic Preparation), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Quality Control of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hernandez-Olmos, Victor; Heering, Jan; Planz, Viktoria; Liu, Ting; Kaps, Alexander; Rajkumar, Rinusha; Gramzow, Matthias; Kaiser, Astrid; Schubert-Zsilavecz, Manfred; Parnham, Michael J.; Windbergs, Maike; Steinhilber, Dieter; Proschak, Ewgenij published the artcile< First Structure-Activity Relationship Study of Potent BLT2 Agonists as Potential Wound-Healing Promoters>, COA of Formula: C8H6BrFO2, the main research area is CAY scaffold based BLT2 agonist wound healing promoter SAR.

The first potent leukotriene B4 (LTB4) receptor type 2 (BLT2) agonists, endogenous 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid (12-HHT), and synthetic CAY10583 (CAY) have been recently described to accelerate wound healing by enhanced keratinocyte migration and indirect stimulation of fibroblast activity in diabetic rats. CAY represents a very valuable starting point for the development of novel wound-healing promoters. In this work, the first structure-activity relationship study for CAY scaffold-based BLT2 agonists is presented. The newly prepared derivatives showed promising in vitro wound-healing activity.

Journal of Medicinal Chemistry published new progress about Drug safety. 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, COA of Formula: C8H6BrFO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Hayhow, Thomas G.; Borrows, Rachel E. A.; Diene, Coura R.; Fairley, Gary; Fallan, Charlene; Fillery, Shaun M.; Scott, James S.; Watson, David W. published the artcile< A Buchwald-Hartwig Protocol to Enable Rapid Linker Exploration of Cereblon E3-Ligase PROTACs**>, Safety of Methyl 3-bromo-2-(bromomethyl)benzoate, the main research area is isoindolyl amine preparation; aryl bromide amine Buchwald Hartwig amination palladium catalyst; PEPPSI; PROTAC; amination; cereblon; drug discovery.

A palladium-catalyzed Buchwald-Hartwig amination for lenalidomide-derived aryl bromides was optimized using high throughput experimentation (HTE) to afford isoindolyl amines I [R1 = H, Me; R2 = n-Bu, Ph, 2-MeC6H4, etc.; R1R2 = (CH2)2O(CH2)2, (CH2)2CH(CH2OH)(CH2)2, (CH2)2N(Boc)(CH2)2, etc.]. The substrate scope of the optimized conditions was evaluated for a range of alkyl- and aryl- amines and functionalised aryl bromides. The methodol. allowed access to new cereblon-based bifunctional proteolysis targeting chimeras with a reduced step count and improved yields.

Chemistry – A European Journal published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 337536-14-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8Br2O2, Safety of Methyl 3-bromo-2-(bromomethyl)benzoate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Woerly, Eric M.; Banik, Steven M.; Jacobsen, Eric N. published the artcile< Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source>, Related Products of 6942-39-8, the main research area is fluoroisochromanone enantioselective synthesis regioselectivity; alkenyl benzoate preparation fluorolactonization; bromobenzoate alkenyl boronic acid pinacol ester.

The enantioselective synthesis of 4-fluoroisochromanones via chiral aryl iodide-catalyzed fluorolactonization is reported. This methodol. uses HF-pyridine as a nucleophilic fluoride source with a peracid stoichiometric oxidant and provides access to lactones containing fluorine-bearing stereogenic centers in high enantio- and diastereoselectivity. The regioselectivity observed in these lactonization reactions is complementary to that obtained with established asym. electrophilic fluorination protocols.

Journal of the American Chemical Society published new progress about Enantioselective synthesis. 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, Related Products of 6942-39-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

He, Ben; Zhang, Sikun; Zhang, Yueyan; Li, Guoping; Zhang, Bingjie; Ma, Wenqiang; Rao, Bin; Song, Ruitong; Zhang, Lei; Zhang, Yanfeng; He, Gang published the artcile< ortho-Terphenylene Viologens with Through-Space Conjugation for Enhanced Photocatalytic Oxidative Coupling and Hydrogen Evolution>, Quality Control of 3959-07-7, the main research area is Terphenylene Viologens Through Space Conjugation Photocatalytic Oxidative Coupling; Enhanced Photocatalytic Oxidative Coupling Hydrogen Evolution WS.

A series of novel ortho-terphenylene viologen derivatives (o-TPV2+) with through-space conjugation (TSC) via the combination of ortho-terphenylene skeletons with viologen structure is reported. Their optoelectronic properties can be adjusted by N-arylation or N-alkylation reactions. Compared with other viologen derivatives, o-TPV2+ not only exhibits strong photoluminescence, but also retards the charge recombination process and stabilizes diradicals state without forming a quinoid structure due to the special TSC effect. Based on their special redox characteristics, o-TPV2+ were applied to the photocatalytic oxidative coupling of benzylamine with 96% yield. In addition, pTA-o-TPV2+ (tethered with p-toluic acid) modified g-C3N4 was used for visible-light-driven hydrogen production for the first time, exceeding 15 times the rate over unmodified g-C3N4.

Journal of the American Chemical Society published new progress about Biradicals Role: PRP (Properties). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Quality Control of 3959-07-7.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhan, Bei-Bei; Wang, Lei; Luo, Jun; Lin, Xu-Feng; Shi, Bing-Feng published the artcile< Synthesis of Axially Chiral Biaryl-2-amines by PdII-Catalyzed Free-Amine-Directed Atroposelective C-H Olefination>, Recommanded Product: 2-Bromo-4-isopropylaniline, the main research area is arylamine palladium chiral spiro phosphoric acid atroposelective olefination catalyst; axially chiral biarylamine stereoselective preparation; C−H olefination; atroposelectivity; biaryl-2-amines; chiral spiro phosphoric acids; palladium.

A simple and ubiquitously present group, free amine, is used as a directing group to synthesize axially chiral biaryl compounds by PdII-catalyzed atroposelective C-H olefination. A broad range of axially chiral biaryl-2-amines can be obtained in good yields with high enantioselectivities (up to 97% ee). Chiral spiro phosphoric acid (SPA) proved to be an efficient ligand and the loading could be reduced to 1 mol % without erosion of enantiocontrol in gram-scale synthesis. The resulting axially chiral biaryl-2-amines also provide a platform for the synthesis of a set of chiral ligands.

Angewandte Chemie, International Edition published new progress about Aromatic amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 51605-97-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H12BrN, Recommanded Product: 2-Bromo-4-isopropylaniline.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kunzendorf, Andreas; Xu, Guangcai; van der Velde, Jesse J. H.; Rozeboom, Henriette J.; Thunnissen, Andy-Mark W. H.; Poelarends, Gerrit J. published the artcile< Unlocking Asymmetric Michael Additions in an Archetypical Class I Aldolase by Directed Evolution>, Reference of 3893-18-3, the main research area is stereoselective Michael addition engineered deoxyribosephosphate aldolase.

Class I aldolases catalyze asym. aldol addition reactions and have found extensive application in the biocatalytic synthesis of chiral β-hydroxy-carbonyl compounds However, the usefulness of these powerful enzymes for application in other C-C bond-forming reactions remains thus far unexplored. The redesign of class I aldolases to expand their catalytic repertoire to include non-native carboligation reactions therefore continues to be a major challenge. Here, we report the successful redesign of 2-deoxy-D-ribose-5-phosphate aldolase (DERA) from Escherichia coli, an archetypical class I aldolase, to proficiently catalyze enantioselective Michael additions of nitromethane to α,β-unsaturated aldehydes to yield various pharmaceutically relevant chiral synthons. After 11 rounds of directed evolution, the redesigned DERA enzyme (DERA-MA) carried 12 amino-acid substitutions and had an impressive 190-fold enhancement in catalytic activity compared to the wildtype enzyme. The high catalytic efficiency of DERA-MA for this abiol. reaction makes it a proficient “”Michaelase”” with potential for biocatalytic application. Crystallog. anal. provides a structural context for the evolved activity. Whereas an aldolase acts naturally by activating the enzyme-bound substrate as a nucleophile (enamine-based mechanism), DERA-MA instead acts by activating the enzyme-bound substrate as an electrophile (iminium-based mechanism). This work demonstrates the power of directed evolution to expand the reaction scope of natural aldolases to include asym. Michael addition reactions and presents opportunities to explore iminium catalysis with DERA-derived catalysts inspired by developments in the organocatalysis field.

ACS Catalysis published new progress about Crystal structure. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Reference of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chen, Ziren; Xue, Fei; Zhang, Yonghong; Jin, Weiwei; Wang, Bin; Xia, Yu; Xie, Mengwei; Abdukader, Ablimit; Liu, Chenjiang published the artcile< Visible-Light-Promoted [3 + 2] Cyclization of Chalcones with 2-Mercaptobenzimidazoles: A Protocol for the Synthesis of Imidazo[2,1-b]thiazoles>, Name: 3-(4-Bromophenyl)acrylaldehyde, the main research area is imidazothiazole preparation photochem; chalcone mercaptobenzimidazole heterocyclization.

A visible-light-promoted [3+2] cyclization between chalcones R 1CH=CHC(O)R2 (R1 = Ph, thiophen-2-yl, naphthalen-2-yl, etc.; R2 = H, Ph, thiophen-2-yl, naphthalen-1-yl, etc.) and 2-mercaptobenzoimidazoles I (R3 = R4 = H, Me, OMe, Cl) for the construction of diverse imidazo[2,1-b]thiazoles II and III, IV via an electron-donor-acceptor (EDA) complex has been developed. This novel aminothiolation can be realized under only visible light irradiation without the aid of external photocatalysts, transition metals, and oxidants. Mechanistic investigations have revealed that the thiol anions and chalcones form EDA complexes, providing a novel strategy for the synthesis of imidazo[2,1-b]thiazoles II, III, and IV.

Organic Letters published new progress about Benzimidazoles Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Dewar, Michael J. S.; Poesche, Werner H. published the artcile< New heteroaromatic compounds. XVIII. Boron-containing analogs of benz[a]anthracene>, Name: 4-Bromoisobenzofuran-1,3-dione, the main research area is .

The amines, 2,3-Ph(H2N)C10H6 (I) and 2-(2-H2NC6H4)C10H7 (II) on treatment with BCl3 and a catalytic amount of AlCl3 in boiling xylene gave the corresponding chloroborazarobenz[a]anthracenes (III, R = Cl) (IV) and (V, R = Cl) (VI). NaNO2 (55 ml., 2M) in concentrated H2SO4 stirred below 25° with addition of 18.8 g. 3,2-O2N(H2N)C10H6 in 670 ml. AcOH (boiled and cooled rapidly to 20°) and the mixture kept 15 min., added with stirring to 38 g. CuBr in 200 ml. 48% HBr and kept overnight, and diluted with H2O yielded 54% 3,2-Br(O2N)C10H6, m. 79-80°. The compound (20.8 g.) and 55 g. PhI stirred 36 hrs. at 110° with 31.8 g. Cu bronze yielded 74% 3,2-Ph(O2N)C10H6 (VII), m. 96.0-6.8° (MeOH). VII (6.0 g.) and 0.2 g. 10% Pd-C in 230 ml. boiling alc. treated gradually with 20 ml. N2H4.H2O and kept 1 hr. yielded quant. I, m. 82.7-3.5° (90% MeOH). I (10 g.) in 160 ml. dry xylene added (N atm.) slowly to 7.0 g. BCl3 in 45 ml. ice-cold xylene and the mixture treated with 0.2 g. AlCl3, the mixture heated to 140° in 4 hrs. and the temperature maintained 16 hrs., cooled and taken up in 750 ml. 2:1 Et2O-C6H6, the H2O-washed and dried (MgSO4) solution evaporated on a steam bath and the residue taken up in 500 ml. hot MeOH, the solution concentrated and kept at -15°, the product recovered from hot MeOH and the purified material (4.2 g.) recrystallized using an efficient dry box gave III (R = OMe) (VIII), m. 159° (evacuated capillary). The mother liquors gave 0.85 g. III (R = 1/2 O), C32H22B2N2O, m. 322°. VIII (1.3 g.) in 40 ml. dry Et2O stirred (H2O-free atm.) at 0° with addition of 12.5 ml. 0.6M MeMgBr and the mixture stirred 24 hrs. with rise of temperature to 20, the filtered solution evaporated and the residue sublimed at 150°/0.005 mm. gave III (R = Me) (VIIIa), m. 160.0-1.3° (petr. ether, b. 60-8°). LiAlH4 (1.35 millimoles) added to 3.86 millimoles VIII in 40 ml. dry Et2O and the mixture refluxed 2 hrs. with 0.45 millimole AlCl3 gave 5,6-borazarobenz[a]anthracene (III, R = H) (IX), m. 139° (decomposition). Cu bronze (46.5 g.), 65.0 g. 2-IC10H7, and 56.0 g. 1,2-Br(O2N)C6H4 stirred 40 hrs. at 110° gave 60% 2-(o-O2NC6H4)C10H7 (X), m. 101° (MeOH). X (9.0 g.) in 450 ml. alc. hydrogenated at 20° and 30 lb./in.2 with 0.3 g. 10% Pd-C and the filtered solution concentrated gave 6.0g. II, m. 95-7°. X (32 g.) and 1.0 g. 10% Pd-C refluxed 1 hr. in 1400 ml. alc. with gradual addition of 45 ml. N2H4.H2C and the filtered solution concentrated gave 22 g. II. II (22.0 g.) in 350 ml. dry xylene added slowly with stirring to 13.0 g. BCl3 in 100 ml. ice-cold xylene and the mixture heated 4 hrs. at 140° with 0.5 g. AlCl3 and stirred 16 hrs. at 140° gave 10.4 g. V (R = 1/2 O) (XI), m. 261-4°, recrystallized from PhMe(C) to give an analytical sample, m. 275.5°. Further concentration of the mother liquors gave a 2nd crop of XI (4.8 g., m. 264-5°), and evaporation of the filtrate yielded 8.6 g. residue (XII), m. 225-47°. The ether XI (12.7 g.) taken up in 500 ml. hot absolute MeOH and concentrated to 350 ml., cooled and the product (10.5 g., m. 174-6°) recrystallized from MeOH (C) gave V (R = OMe) (XIII), m. 183-4° (evacuated capillary). The filtrate evaporated and the residue combined with XII, the mixture recrystallized from absolute MeOH to give 4.80 g. XIII, and the filtrate evaporated in vacuo gave a dark brown oil with an ultraviolet spectrum identical with that of XIII and containing no other bands. XIII (2.6 g.) stirred at 20° in 100 ml. dry Et2O with dropwise addition of 15 ml. M MeMgBr in Et2O and the mixture stirred 2 hrs., the filtered solution diluted with moist Et2O and shaken with H2O, the organic layer dried over CaCl2 and evaporated yielded 87% product, m. 136-40°, sublimed at 120°/0.1 mm. to give V (R = Me) (XIV), m. 141-3°. XIII (1.00 g.) stirred at 0° in 30 ml. dry Et2O with gradual addition of 1.00 millimole LiAlH4 (standardized Et2O solution) and the mixture refluxed 2 hrs. with 0.04 g. AlCl3, the filtered solution evaporated and the residue sublimed at 120°/0.005 mm. gave 65% V (R = H) (XV), m. 136.5-7.0° (decomposition). XIII (2.0 g.) in 20 ml. hot AcOH treated with 10 ml. concentrated HCl and the mixture cooled quickly to 5°, diazotized with 0.60 g. NaNO2 in a min. of H2O and kept 2 hrs., added with stirring to 300 ml. boiling H2O and the mixture boiled 30 min., kept overnight and the precipitate recrystallized twice from PhMe(C) gave 64% 6-hydroxy-6,5-boroxarobenz[a]-anthracene (XVI), m. 279.5-81.0°. The cyclization of II to V rather than to a borazachrysene illustrated very clearly the large steric requirements of the Friedel-Crafts reaction. The charge transfer spectra of the complexes formed by III and V with tetracyanoethylene (XVII) were determined in CHCl3. No difficulty was encountered with the Me or MeO derivatives, VIII, VIIIa, XIII, or XIV, all of which gave stable colorations with XVII, but the parent compounds, IX and XV, reacted rapidly with the acceptor. XV in CHCl3 and XVII in CHCl3 initially gave a green mixture rapidly changing to violet before fading and forming a white precipitate The ultraviolet spectrum of the final colorless solution was identical with that of XIII, suggesting that EtOH in the CHCl3 was forming V (R = OEt) and precipitating (NC)2CHCH(CN)2. The wave lengths of the charge transfer spectra of XVII complexes are given (compound and wave lengths of charge transfer band in A given): IX, 614; VIII, 627; VIIIa, 620; XV, 690, 477; XIII, 701, 500; XIV, 704, 486. The π-electron distribution in these compounds is probably too uneven for first-order perturbation theory to be applicable. The ultra violet spectra of IX and XV in methylcyclohexane and alc.-free CHCl3, and of VIII, XIII, VIIIa, and XIV in CHCl3 were tabulated with the spectrum of benz[a]anthracene (XVIII) in methylcyclohexane listed for comparison. The estimated band maximum (mμ of π-π transitions in methyl cyclohexane for XVIII, IX, and XV were tabulated. The spectra of IX and XV are very similar to that of XVIII, the main difference being an increase in intensity of the α-bands in the hetero aromatics, in accordance with theory.

Journal of the American Chemical Society published new progress about Entropy. 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Name: 4-Bromoisobenzofuran-1,3-dione.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary