Category: 25637-16-5

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.Name: 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: 25637-16-5Name: 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

HPLC of Formula: 25637-16-5In 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: 25637-16-5HPLC 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

In 2018,Rohe, Samantha; McCallum, Terry; Morris, Avery O.; Barriault, Louis published 《Transformations of Isonitriles with Bromoalkanes Using Photoredox Gold Catalysis》.Journal of Organic Chemistry published the findings.Safety of 4-Bromotetrahydropyran The information in the text is summarized as follows:

Isonitriles have excellent electronic compatibility to react with free radicals. Recently, photoredox catalysis has emerged as a powerful tool for the construction of C-C bonds with few protocols for alkylative heterocycle synthesis through isonitrile addition Herein, it is describe the photocatalytic generation of alkyl radicals from unactivated bromoalkanes as part of an efficient cross-coupling strategy for the diversification of isonitriles using a dimeric gold(I) photoredox catalyst, [Au2(dppm)2]Cl2. In addition to this study using 4-Bromotetrahydropyran, there are many other studies that have used 4-Bromotetrahydropyran(cas: 25637-16-5Safety of 4-Bromotetrahydropyran) 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.Safety of 4-Bromotetrahydropyran

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

Delgado, Pete; Glass, Raoul J.; Geraci, Gina; Duvadie, Rohit; Majumdar, Dyuti; Robinson, Richard I.; Elmaarouf, Imran; Mikus, Malte; Tan, Kian L. published an article in 2021. The article was titled 《Use of Green Solvents in Metallaphotoredox Cross-Electrophile Coupling Reactions Utilizing Lipophilic Modified Dual Ir/Ni Catalyst System》, and you may find the article in Journal of Organic Chemistry.Name: 4-Bromotetrahydropyran The information in the text is summarized as follows:

Facilitating photoredox coupling reactions in process friendly green solvents was achieved by the successful application of the dual Ir/Ni catalyst system with enhanced solubility properties. These photochem. reactions (specifically Br-Br sp2-sp3 cross electrophile coupling) are reported in a head to head comparison to the reactions using standard di-t-Bu bipyridine ligand Ir/Ni catalyst system. This presentation highlights the benefits of altering the solubility properties of the ligands used in the Ir/Ni dual catalyst. The experimental part of the paper was very detailed, including the reaction process of 4-Bromotetrahydropyran(cas: 25637-16-5Name: 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.Name: 4-Bromotetrahydropyran

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

In 2018,Zhang, Rui; Li, Guoqing; Wismer, Michael; Vachal, Petr; Colletti, Steven L.; Shi, Zhi-Cai published 《Profiling and Application of Photoredox C(sp3)-C(sp2) Cross-Coupling in Medicinal Chemistry》.ACS Medicinal Chemistry Letters published the findings.Computed Properties of C5H9BrO The information in the text is summarized as follows:

Recent visible-light photoredox catalyzed C(sp3)-C(sp2) cross-coupling provides a novel transformation to potentially enable the synthesis of medicinal chem. targets. Here, we report a profiling study of photocatalytic C(sp3)-C(sp2) cross-coupling, both decarboxylative coupling and cross-electrophile coupling, with 18 pharmaceutically relevant aryl halides by using either Kessil lamp or our newly developed integrated photoreactor. Integrated photoreactor accelerates reaction rate and improves reaction success rate. Cross-electrophile coupling gives higher success rate with broad substrate scope on alkyl halides than that of the decarboxylative coupling. In addition, a successful application example on a discovery program demonstrates the efficient synthesis of medicinal chem. targets via photocatalytic C(sp3)-C(sp2) cross-coupling by using our integrated photoreactor. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5Computed Properties of C5H9BrO)

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.Computed Properties of C5H9BrO

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

In 2022,Zhou, Xiao; Guo, Lin; Zhang, Haoxiang; Xia, Raymond Yang; Yang, Chao; Xia, Wujiong published an article in Advanced Synthesis & Catalysis. The title of the article was 《Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process》.Safety of 4-Bromotetrahydropyran The author mentioned the following in the article:

A sustainable Ni-catalyzed reductive acylation reaction of carboxylic acids via an electrochem. pathway was presented, affording a ketones ArC(O)R [Ar = Ph, 4-MeC6H4, 4-PhC6H4, etc.; R = n-Bu, CH(Me)2, CH2Cy, etc.] as major products. The reaction proceeded at ambient temperature using unactivated alkyl halides and N-hydroxyphthalimide (NHP) esters as coupling partners, which exhibited several synthetic advantages, including mild conditions and convenience of amplification (58% yield for 6 mmol scale reaction). In the part of experimental materials, we found many familiar compounds, such as 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,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

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

《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

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