Tag: 100-200

In 2022,Wu, Ying-Ai; Wang, Rui-An; Jiang, Shu-Yun; Jiang, Tai-Bai; Song, Jun-Rong; Shi, Jun; Wu, Wei; Pan, Wei-Dong; Ren, Hai published an article in Green Chemistry. The title of the article was 《Water enables the tunable electrochemical synthesis of heterocyclic 3a- or 5a-bromoindolines》.Category: chlorides-buliding-blocks The author mentioned the following in the article:

Due to the electron-richness of the C3/C2 positions of the indole moiety, direct nucleophilic bromination at the C5-position of tryptophol and tryptamine derivatives is difficult and remains unexplored. Herein, authors report a tunable water-mediated electrooxidative protocol for the dearomative C3/C5-bromocyclization of tryptophol and tryptamine derivatives This electrosynthetic approach enables selective construction of cyclic 3a- or 5a-bromoindolines simply by the addition of different amounts of water, with no addnl. electrolytes, external oxidants, or additives being required. Less water delivers the cyclic 3a-bromoindoline, while more water delivers the 5a-bromoindoline. A detailed mechanistic study showed that an unexpected collaborative bromide ionic electrooxidation at the anode and reductive hydrodebromination at the cathode in the presence of more water is key to the tunable chemoselectivity control. In the experiment, the researchers used Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Category: chlorides-buliding-blocks)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Category: chlorides-buliding-blocks

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Gargaro, Samantha L.; Dunson, Bre’Shon; Sieber, Joshua D. published an article in 2021. The article was titled 《Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene》, and you may find the article in Synlett.Computed Properties of C6H6BFO2 The information in the text is summarized as follows:

The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this process likely occurs through a rare protonolysis/s transmetalation event rather than by the well-established mechanism requiring the involvement of O2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products was obtained by employing dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand. In the experimental materials used by the author, we found (3-Fluorophenyl)boronic acid(cas: 768-35-4Computed Properties of C6H6BFO2)

(3-Fluorophenyl)boronic acid(cas: 768-35-4) can be used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.Computed Properties of C6H6BFO2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Wang, Shihui; Xu, Jian; Song, Qiuling published an article in 2021. The article was titled 《Modular Synthesis of Polysubstituted Quinolin-3-amines by Oxidative Cyclization of 2-(2-Isocyanophenyl)acetonitriles with Organoboron Reagents》, and you may find the article in Organic Letters.Name: (3-Fluorophenyl)boronic acid The information in the text is summarized as follows:

A protocol with Mn(III) acetate as a mild one-electron oxidant promoting a radical process to construct polysubstituted quinolin-3-amines was reported. 2-(2-Isocyanophenyl)acetonitriles and organoboron reagents were suitable substrates for this reaction. The remarkable advantages of this protocol were the practical method, mild approach, high reaction efficiency and good compatibility of functional groups, providing straightforward access to functional quinoline derivatives After reading the article, we found that the author used (3-Fluorophenyl)boronic acid(cas: 768-35-4Name: (3-Fluorophenyl)boronic acid)

(3-Fluorophenyl)boronic acid(cas: 768-35-4) can be used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.Name: (3-Fluorophenyl)boronic acid

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

《Structure-activity relationship study of gatastatin based on the topliss tree approach》 was written by Hayakawa, Ichiro; Shioda, Shuya; Chinen, Takumi; Usui, Takeo; Kigoshi, Hideo. Category: chlorides-buliding-blocks And the article was included in Heterocycles in 2019. The article conveys some information:

Various analogs of gatastatin I [Ar = 3-ClC6H4, 4-MeC6H4, 4-tButC6H4, etc.], a γ-tubulin-specific inhibitor, were designed and synthesized by systematically optimizing the aromatic ring at the O7-benzyl group in accordance with an operational Topliss tree, and their biol. activities were evaluated. Some derivatives showed stronger cytotoxicity against HeLa cells than gatastatin. Especially, the cytotoxicity of the I [Ar = 3-ClC6H4] derivative was about 18-fold stronger than that of gatastatin. However, these derivatives did not exhibit binding ability to the yeast γ-tubulin small complex or inhibitory activity against α,β-tubulin polymerization These results suggested that γ-tubulin strongly recognized the unsubstituted Ph ring of the O7-benzyl group in gatastatin.3-Chlorobenzylchloride(cas: 620-20-2Category: chlorides-buliding-blocks) was used in this study.

3-Chlorobenzylchloride(cas: 620-20-2) has been used in the reaction of 3-methoxybenzyl chloride and ethyl 4-bromobenzoate in pure water, using zinc dust and a Pd catalyst.Category: chlorides-buliding-blocks

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Liu, Zhi-Yun; Cook, Silas P. published an article in 2022. The article was titled 《Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds》, and you may find the article in Organic Letters.Recommanded Product: Methyl 2-chloro-2-oxoacetate The information in the text is summarized as follows:

Herein, authors describe a nickel-catalyzed reductive arylation of remote C(sp3)-H bonds with aryl electrophiles. The reaction targets secondary and tertiary C(sp3)-H bonds to deliver all-carbon quaternary centers. The success of this method relies on a novel amidyl radical precursor that tolerates reducing conditions-O-oxalate hydroxamic acid esters. After reading the article, we found that the author used Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Recommanded Product: Methyl 2-chloro-2-oxoacetate)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Recommanded Product: Methyl 2-chloro-2-oxoacetate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Liu, Bingxian; Yang, Lingyun; Dong, Zhenzhen; Chang, Junbiao; Li, Xingwei published an article in 2021. The article was titled 《Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes》, and you may find the article in Organic Letters.Synthetic Route of C6H6BFO2 The information in the text is summarized as follows:

Rhodium(III)-catalyzed annulation of 2-biphenylboronic acids I (R = R1 = H; R = 4-Me, R1 = 4-Me; R = 6-MeO, R1 = 2′-MeO; R = 5-F, R1 = 3′-F; etc.) with three classes of activated alkenes, e.g., (E)-R2C(O)CH=CHCF3 (R2 = 4-MeC6H4, naphthalen-1-yl, furan-2-yl, etc.), II (R3 = n-Pr, Ph, 2-BrC6H4, etc.), and cyclohex-2-en-1-one, has been realized, leading to the synthesis of fused or bridged cyclic skeletons, e.g., III (R4 = R5 = H; R4 = 2-Me, R5 = 7-Me; R4 = 4-MeO, R5 = 5-MeO ) and IV (R6 = R7 = H; R6 = 1-F, R7 = 11-F; R6 = 3-tert-Bu, R7 = 9-tert-Bu; etc.), via transmetalation-initiated C-H activation. In the annulative coupling of 2-biphenylboronic acid with a CF3-substituted enone, the bulky cyclopentadienyl ligand (CptBu) in the catalyst proved effective in promoting the reductive elimination process prior to protonolysis, affording the [4+2]-annulated products III instead of the simple 1,4-addition product. Seven-membered rings IV were obtained when disubstituted cyclopropenones II were employed. Bridged cycles V (R8 = H, Me) and 2-(tert-butyl)triphenylene-1,4-dione were isolated from the coupling of 2-biphenylboronic acid with benzoquinone, 2-methylbenzoquinone, and 2-(tert-butyl)benzoquinone as a result of 2-fold Michael additions The substrate scopes were found to be broad with up to 99% yield under air-tolerant conditions. In the experiment, the researchers used (3-Fluorophenyl)boronic acid(cas: 768-35-4Synthetic Route of C6H6BFO2)

(3-Fluorophenyl)boronic acid(cas: 768-35-4) can be used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.Synthetic Route of C6H6BFO2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Cui, Guo-Qing; Dai, Jing-Cheng; Li, Yan; Li, Yuan-Bo; Hu, Duo-Duo; Bian, Kang-Jie; Sheng, Jie; Wang, Xi-Sheng published their research in Organic Letters in 2021. The article was titled 《Copper-Catalyzed Enantioselective Arylation via Radical-Mediated C-C Bond Cleavage: Synthesis of Chiral ω,ω-Diaryl Alkyl Nitriles》.Computed Properties of C6H6BFO2 The article contains the following contents:

The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters to access ω,ω-diaryl alkyl nitriles has been developed in high yield (up to 92% yield) with excellent enantioselectivity (up to 91% ee). Side-arm bis(oxazoline) ligand plays a significant role in this asym. catalytic transformation, which provides an efficient route to construct diverse chiral ω,ω-diaryl alkyl nitriles. Synthetic utility has also been demonstrated in the further derivatization of the ω,ω-diaryl alkyl nitrile to corresponding amide. In the experiment, the researchers used (3-Fluorophenyl)boronic acid(cas: 768-35-4Computed Properties of C6H6BFO2)

(3-Fluorophenyl)boronic acid(cas: 768-35-4) can be used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.Computed Properties of C6H6BFO2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

《Electrochemical Radical-Radical Cross-Coupling Approach between Sodium Sulfinates and 2H-Indazoles to 3-Sulfonylated 2H-Indazoles》 was written by Kim, Wansoo; Kim, Hun Young; Oh, Kyungsoo. Recommanded Product: Thiophene-2-sulfonyl chloride And the article was included in Organic Letters in 2020. The article conveys some information:

A direct cross-coupling between sodium sulfinates and 2H-indazoles has been developed under electrochem. conditions. The utilization of a graphite anode and platinum cathode in an undivided cell with a constant current of 7 mA allowed the concurrent oxidations of sulfinates and 2H-indazoles to sulfonyl radical and radical cationic 2H-indazoles, facilitating the direct radical-radical coupling strategy to 3-sulfonylated 2H-indazole derivatives The transition-metal- and redox-reagent-free synthetic approach should serve as a valuable synthetic tool to achieve heteroaromatic compounds In the experiment, the researchers used many compounds, for example, Thiophene-2-sulfonyl chloride(cas: 16629-19-9Recommanded Product: Thiophene-2-sulfonyl chloride)

Thiophene-2-sulfonyl chloride(cas: 16629-19-9) is a member of sulfonyl chlorides. Sulfonyl chlorides are reactive sulfonic acid derivatives similar in properties and reactivity to acid chlorides of carboxylates. The sulfonic acid group, however, is a highly hindered molecule, containing a tetrahedral configuration of substituents. Recommanded Product: Thiophene-2-sulfonyl chloride

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Chen, Wangzhe; Ni, Shengyang; Wang, Yi; Pan, Yi published an article in 2022. The article was titled 《Electrochemical-Promoted Nickel-Catalyzed Reductive Allylation of Aryl Halides》, and you may find the article in Organic Letters.Application In Synthesis of Methyl 2-chloro-2-oxoacetate The information in the text is summarized as follows:

Compared with conventional reductive coupling, reductive coupling under electrochem. conditions without external reductants is greener, milder, and more efficient and is of increasing interest to organic chemists. In this work, authors report the sacrificial anode, nickel-catalyzed electrochem. allylation reaction of aryl and alkyl halides. The reaction can be applied to a range of allylation reagents such as trifluoroalkenes, oxalates, and acetates. In the part of experimental materials, we found many familiar compounds, such as Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Application In Synthesis of Methyl 2-chloro-2-oxoacetate)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Application In Synthesis of Methyl 2-chloro-2-oxoacetate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Liu, Qi; Zheng, Jian; Zhang, Xue; Ma, Shengming published an article in 2022. The article was titled 《Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process》, and you may find the article in Nature Communications.Quality Control of Methyl 2-chloro-2-oxoacetate The information in the text is summarized as follows:

Different from the traditional two-electron oxidative addition-transmetalation-reductive elimination coupling strategy, visible light has been successfully integrated into transition metal-catalyzed coupling reaction of propargylic alc. derivatives e.g., 1-ethynylcyclohexyl Me oxalate highly selectively forming allenenitriles e.g., 3-cyclohexylideneprop-2-enenitrile specifically speaking, visible light-mediated Cu-catalyzed cyanation of propargylic oxalates has been realized for the general, efficient, and exclusive syntheses of di-, tri, and tetra-substituted allenenitriles bearing various synthetically versatile functional groups. A set of mechanistic studies, including fluorescence quenching experiments, cyclic voltammetric measurements, radical trapping experiments, control experiments with different photocatalyst, and DFT calculation studies have proven that the current reaction proceeds via visible light-induced redox-neutral reductive quenching radical mechanism, which is a completely different approach as compared to the traditional transition metal-catalyzed two-electron oxidative addition processes. The results came from multiple reactions, including the reaction of Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Quality Control of Methyl 2-chloro-2-oxoacetate)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Quality Control of Methyl 2-chloro-2-oxoacetate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics