Category: bromides-buliding-blocks

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

Mayuranathan, P. S. published the artcile< Thermal decomposition of mercuric o- and m-nitrobenzoate and 4-nitrophthalate>, Reference of 16426-64-5, the main research area is .

(o-O2NC6H4CO2)2Hg (18 g.) heated at 180° until evolution of CO2 ceased (4 hrs.) gave 16% (o-O2NC6H4)2Hg (I), a crystalline solid insoluble in organic solvents. I (4 g.) heated 1 hr. with 20 cc. 2M K perbromide or periodide, the resulting oils freed from halogen, and crystallized gave 1 g. o-BrC6H4NO2, m. 39°, or o-IC6H4NO2, m. 49°, resp. (m-O2NC6H4CO2)2Hg (II) did not decompose but gave anhydro-2-hydroxymercuri-3-nitrobenzoic acid (III). Thus, 10 g. II heated 6 hrs. at 190° gave III, soluble in warm alkali. III (5 g.) similarly treated with K perbromide or periodide, the solution evaporated to remove excess halogen, acidified, and extracted with Et2O, the solution washed with thiosulfate, dried, and evaporated gave 1 g. 2,3-Br(O2N)C6H3CO2H, m. 185°, and 2,3-I(O2N)C6H3CO2H, m. 205°, resp. 4-Nitrophthalic acid (23 g.) in 16 g. Na2CO3 dissolved in 20 cc. H2O treated with 45 g. Hg(OAc2) in 150 cc. H2O containing 1 cc. AcOH gave Hg 4-nitrophthalate (IV). IV (20 g.) heated 6 hrs. at 190° gave anhydro-2-hydroxymercuri-4-nitrobenzoic acid (V), identical with the product obtained from p-O2NC6H4CO2H (VI). V brominated or iodinated as above gave 2-Br- and 2,4-I(O2N)C6H3CO2H. Hydrolysis of V gave VI.

Journal of the Chemical Society published new progress about 16426-64-5. 16426-64-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrNO4, Reference of 16426-64-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Yingying; Li, Peihe; Wang, Jinghui; Liu, Zhifei; Wang, Yin; Lu, Ye; Liu, Ying; Duan, Limei; Li, Wanfei; Sarina, Sarina; Zhu, Huaiyong; Liu, Jinghai published the artcile< Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride>, SDS of cas: 2725-82-8, the main research area is iron phosphotungstate dual metal site fabricated carbon nitride photocatalyst; ketone preparation alkane alc selective oxidation photochem.

Here, a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ = 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride was reported. The optimized cation (C) of Fe3+ or Ni2+, with an anion (A) of phosphotungstate (PW123-) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12 dual-metal-site as a model, a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples) was demonstrated. The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4 that is mediated by the tBuO ̇and tBuOO ̇radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature In addition, this A-C/g-C3N4 photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

Catalysis Science & Technology published new progress about Alcohols 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

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

Huan, Leitao; Shu, Xiaomin; Zu, Weisai; Zhong, De; Huo, Haohua published the artcile< Asymmetric benzylic C(sp3)-H acylation via dual nickel and photoredox catalysis>, Electric Literature of 2725-82-8, the main research area is alpha aryl ketone enantioselective preparation photochem; alkylarene carboxylic acid benzylic carbon hydrogen acylation nickel photocatalyst; photochem alpha aryl ester enantioselective preparation; phenyl chloroformate alkylarene coupling nickel photocatalyst.

An asym. benzylic C-H acylation of alkylarenes employing carboxylic acids as acyl surrogates for synthesis of α-aryl ketones I [R1 = Me, 2-thienyl, 2-naphthyl, etc.; R2 = Me, Et, CH2CH2OAc, etc.; Ar = 3-thienyl, 4-FC6H4, 1,1′-biphenyl, etc.] via nickel and photoredox dual catalysis was reported. This mild yet straightforward protocol transformed a diverse array of feedstock carboxylic acids and simple alkyl benzenes into highly valuable α-aryl ketones with high enantioselectivities. The utility of this method was showcased in gram-scale synthesis and late-stage modification of medicinally relevant mols. Mechanistic studies suggested a photocatalytically generated bromine radical could perform benzylic C-H cleavage to activate alkylarenes as nucleophilic coupling partners which could then engage in a nickel-catalyzed asym. acyl cross-coupling reaction. This bromine-radical-mediated C-H activation strategy could be also applied to enantioselective coupling of alkylarenes with chloroformate for synthesis of chiral α-aryl esters, e.g., II.

Nature Communications published new progress about Acylation catalysts (stereoselective). 2725-82-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H9Br, Electric Literature of 2725-82-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Du, Yufeng; Huang, Linyu; Wang, Neng; Li, Xiaohuan; Zhou, Xian-Li; Zhang, Lan; Huang, Shuai; Walsh, Patrick J.; Gao, Feng published the artcile< Rhodium-Catalyzed Direct Arylation of Furopyridine: Synthesis and the Cardiac Effects of Dictamnine Derivatives>, SDS of cas: 401-78-5, the main research area is aryl furopyridine preparation chemoselective; furopyridine aryl bromide arylation rhodium catalyst; furoquinoline preparation chemoselective; dictamnine aryl bromide arylation rhodium catalyst.

Synthesis of Rh2(OAc)4/IMes·HCl system promotes the chemoselective installation of aryl groups at the 2-position of furo[2,3-b]pyridines I (R = Ph, naphthalen-1-yl, 2,3-dihydro-1,4-benzodioxin-6-yl, etc.) (53-94% yields). The method is applicable to the direct modification of the natural furoquinoline alkaloid dictamnine. The cardiac effects of the fluorinated analogs II were improved, and compared to dictamnine at 160μg/mL. Preliminary mechanism of action studies indicate that the effects might be related to epinephrine αreceptors, M-receptor and calcium channel receptor.

Advanced Synthesis & Catalysis published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, SDS of cas: 401-78-5.

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