Day: October 11, 2022

The author of 《Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions》 were Pang, Haobo; Wang, Ye; Gallou, Fabrice; Lipshutz, Bruce H.. And the article was published in Journal of the American Chemical Society in 2019. HPLC of Formula: 25637-16-5 The author mentioned the following in the article:

The combination of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide leads, in the presence of Zn and a catalytic amount of an Fe(II) salt, to a net reductive coupling. The new C-C bond is regiospecifically formed at rt at the β-site of the alkene. The coupling only occurs in an aqueous micellar medium, where a radical process is likely, supported by several control experiments A mechanism based on these data is proposed. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5HPLC of Formula: 25637-16-5)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.HPLC of Formula: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

He, Rong-De; Bai, Yunfei; Han, Guan-Yu; Zhao, Zhen-Zhen; Pang, Xiaobo; Pan, Xiaobo; Liu, Xue-Yuan; Shu, Xing-Zhong published an article in 2022. The article was titled 《Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis》, and you may find the article in Angewandte Chemie, International Edition.Application In Synthesis of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides was reported. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that was used to add more structural complexity and mol. diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biol. active mols., and it affords access to useful building blocks. Preliminary mechanistic studies revealed that the Ni(I) species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles. In the experimental materials used by the author, we found 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

《Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp2)-C(sp3) Cross-Coupling Methods by Library Synthesis》 was published in ACS Medicinal Chemistry Letters in 2020. These research results belong to Dombrowski, Amanda W.; Gesmundo, Nathan J.; Aguirre, Ana L.; Sarris, Katerina A.; Young, Jonathon M.; Bogdan, Andrew R.; Martin, M. Cynthia; Gedeon, Shasline; Wang, Ying. Name: 4-Bromotetrahydropyran The article mentions the following:

Despite recent advances in the field of C(sp2)-C(sp3) cross-couplings and the accompanying increase in publications, it can be hard to determine which method is appropriate for a given reaction when using the highly functionalized intermediates prevalent in medicinal chem. Thus a study was done comparing the ability of seven methods to directly install a diverse set of alkyl groups on “”drug-like”” aryl structures via parallel library synthesis. Each method showed substrates that it excelled at coupling compared with the other methods. When analyzing the reactions run across all of the methods, a reaction success rate of 50% was achieved. Whereas this is promising, there are still gaps in the scope of direct C(sp2)-C(sp3) coupling methods, like tertiary group installation. The results reported herein should be used to inform future syntheses, assess reaction scope, and encourage medicinal chemists to expand their synthetic toolbox. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Name: 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Name: 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Duvadie, Rohit; Pomberger, Alexander; Mo, Yiming; Altinoglu, Erhan I.; Hsieh, Hsiao-Wu; Nandiwale, Kakasaheb Y.; Schultz, Victor L.; Jensen, Klavs F.; Robinson, Richard I. published an article in 2021. The article was titled 《Photoredox Iridium-Nickel Dual Catalyzed Cross-Electrophile Coupling: From a Batch to a Continuous Stirred-Tank Reactor via an Automated Segmented Flow Reactor》, and you may find the article in Organic Process Research & Development.Product Details of 25637-16-5 The information in the text is summarized as follows:

Organic reaction optimization for batch to flow transfer represents a main challenge for process chemists in drug synthesis. Several factors such as reactant concentration, residence/reaction time, or homo-/heterogeneity need to be taken into consideration during the fine-tuning of reaction conditions toward typical scale-up goals, such as high space-time yield. Herein, we present reaction optimization for photoredox iridium-nickel dual catalyzed cross-electrophile coupling with a focus on developing homogeneous starting conditions. During the screening, special attention was put on the replacement of inorganic bases with homogeneous organic bases, and the effect of pKa on the reaction yield was investigated. Screening was conducted via an automated segmented flow reactor at 15μL scale, and subsequentially, the conditions were transferred to a 5 mL photo-continuous stirred-tank reactor (CSTR) cascade to demonstrate multigram continuous flow synthesis during a 24 h steady operation. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Product Details of 25637-16-5) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Product Details of 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2022,Romano, Ciro; Talavera, Laura; Gomez-Bengoa, Enrique; Martin, Ruben published an article in Journal of the American Chemical Society. The title of the article was 《Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp3 C-O Bonds in Cyclic Acetals》.Formula: C5H9BrO The author mentioned the following in the article:

A dual catalytic manifold that enables site-selective functionalization of unactivated sp3 C-O bonds in cyclic acetals with aryl and alkyl halides is reported. The reaction is triggered by an appropriate σ*-p orbital overlap prior to sp3 C-O cleavage, thus highlighting the importance of conformational flexibility in both reactivity and site selectivity. The protocol is characterized by its excellent chemoselectivity profile, thus offering new vistas for activating strong σ sp3 C-O linkages. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Formula: C5H9BrO) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Formula: C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Application In Synthesis of 4-BromotetrahydropyranIn 2018 ,《Bench-Stable Stock Solutions of Silicon Grignard Reagents: Application to Iron- and Cobalt-Catalyzed Radical C(sp3)-Si Cross-Coupling Reactions》 was published in Angewandte Chemie, International Edition. The article was written by Xue, Weichao; Shishido, Ryosuke; Oestreich, Martin. The article contains the following contents:

A robust method for the preparation of silicon-based magnesium reagents is reported. The MgBr2 used in the lithium-to-magnesium transmetalation step is generated in situ from 1,2-dibromoethane and elemental magnesium in hot THF. No precipitation of MgBr2 occurs in the heat, and transmetalation at elevated temperature leads to homogeneous stock solutions of the silicon Grignard reagents that are stable and storable in the fridge. This method avoids the preparation of silicon pronucleophiles such as Si-Si and Si-B reagents. The new Grignard reagents were applied to unprecedented iron- and cobalt-catalyzed cross-coupling reactions of unactivated alkyl bromides. The functional-group tolerance of these magnesium reagents is excellent. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Application In Synthesis of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2017,Zhou, Wen-Jun; Cao, Guang-Mei; Shen, Guo; Zhu, Xing-Yong; Gui, Yong-Yuan; Ye, Jian-Heng; Sun, Liang; Liao, Li-Li; Li, Jing; Yu, Da-Gang published 《Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides》.Angewandte Chemie, International Edition published the findings.Safety of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Reported herein is a novel visible-light photoredox system with Pd(PPh3)4 as the sole catalyst for the realization of the first direct cross-coupling of C(sp3)-H bonds in N-aryl tetrahydroisoquinolines with unactivated alkyl bromides. Moreover, intra- and intermol. alkylations of heteroarenes were also developed under mild reaction conditions. A variety of tertiary, secondary and primary alkyl bromides undergo reaction to generate C(sp3)-C(sp3) and C(sp2)-C(sp3) bonds in moderate to excellent yields. These redox-neutral reactions feature broad substrate scope (>60 examples), good functional-group tolerance and facile generation of quaternary centers. Mechanistic studies indicate that the simple palladium complex acts as the visible-light photocatalyst and radicals are involved in the process. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Safety of 4-Bromotetrahydropyran)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity; preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives; synthesis of gephyrotoxin via the Schmidt reaction.Safety of 4-Bromotetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2022,Ben-Tal, Yael; Lloyd-Jones, Guy C. published an article in Journal of the American Chemical Society. The title of the article was 《Kinetics of a Ni/Ir-Photocatalyzed Coupling of ArBr with RBr: Intermediacy of ArNiII(L)Br and Rate/Selectivity Factors》.Electric Literature of C5H9BrO The author mentioned the following in the article:

The Ni/Ir-photocatalyzed coupling of an aryl bromide (ArBr) with an alkyl bromide (RBr) has been analyzed using in situ LED-19F NMR spectroscopy. Four components (light, [ArBr], [Ni], [Ir]) are found to control the rate of ArBr consumption, but not the product selectivity, while two components ([(TMS)3SiH], [RBr]) independently control the product selectivity, but not the rate. A major resting state of nickel has been identified as ArNiII(L)Br, and 13C-isotopic entrainment is used to show that the complex undergoes Ir-photocatalyzed conversion to products (Ar-R, Ar-H, Ar-solvent) in competition with the release of ArBr. A range of competing absorption and quenching effects lead to complex correlations between the Ir and Ni catalyst loadings and the reaction rate. Differences in the Ir/Ni Beer-Lambert absorption profiles allow the rate to be increased by the use of a shorter-wavelength light source without compromising the selectivity. A minimal kinetic model for the process allows simulation of the reaction and provides insights for optimization of these processes in the laboratory In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Electric Literature of C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Electric Literature of C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2017,Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao published 《Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature》.Journal of the American Chemical Society published the findings.SDS of cas: 25637-16-5 The information in the text is summarized as follows:

The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chems. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, authors report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. Also rationalized that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 25637-16-5) was used in this study.

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.SDS of cas: 25637-16-5

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

In 2017,Zhang, Xiaheng; MacMillan, David W. C. published 《Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis》.Journal of the American Chemical Society published the findings.COA of Formula: C5H9BrO The information in the text is summarized as follows:

A mechanism that enables direct aldehyde C-H functionalization has been achieved via the synergistic merger of photoredox, nickel, and hydrogen atom transfer catalysis. This mild, operationally simple protocol transforms a wide variety of com. available aldehydes, along with aryl or alkyl bromides, into the corresponding ketones in excellent yield. This C-H abstraction coupling technol. has been successfully applied to the expedient synthesis of the medicinal agent haloperidol. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5COA of Formula: C5H9BrO)

4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.COA of Formula: C5H9BrO

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics