Day: October 13, 2022

《Photoredox Catalysis for Silyl-Mediated C-H Alkylation of Heterocycles with Non-Activated Alkyl Bromides》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Perkins, James J.; Schubert, Jeffrey W.; Streckfuss, Eric C.; Balsells, Jaume; ElMarrouni, Abdellatif. Application of 25637-16-5 The article mentions the following:

The development of a Minisci reaction of electron-deficient heteroarenes with non-activated alkyl bromides under visible-light photoredox catalysis is disclosed. Optimization of the reaction led to identification of mild, general, and practical reaction conditions compatible with sensitive functional groups. The scope of this transformation allowed late-stage functionalization of pharmaceutical products containing electron-deficient heteroarenes in a parallel fashion. The experimental process involved the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Application of 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.Application of 25637-16-5

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

Category: tetrahydropyranIn 2019 ,《Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting CpXRhIII-Catalyzed C-H Functionalization》 was published in Angewandte Chemie, International Edition. The article was written by Brauns, Marcus; Cramer, Nicolai. The article contains the following contents:

In the presence of a nonracemic cyclopentacyclooctadinaphthalene rhodium complex and N-phthalimido-L-phenylalanine, racemic aryl sulfoximines underwent kinetic resolution by C-H activation and cyclocondensation reactions with diazo compounds such as MeCOC(:N2)CO2Et in MeOH to yield nonracemic sulfoximines such as I and nonracemic benzothiazinones such as II. The method was used for the formal syntheses of two kinase inhibitors. After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Category: tetrahydropyran)

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.Category: tetrahydropyran

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

In 2018,Wang, Chengpeng; Dong, Guangbin published 《Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade》.Journal of the American Chemical Society published the findings.Safety of 4-Bromotetrahydropyran The information in the text is summarized as follows:

We report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic ketones, as well as α-branched aldehydes, are suitable substrates for coupling with secondary and tertiary alkyl bromides. Concise formal synthesis of Zanapezil is achieved using this β-alkylation method. 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: 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

《Ir/Ni photoredox dual catalysis with heterogeneous base enabled by an oscillatory plug flow photoreactor》 was written by Debrouwer, Wouter; Kimpe, Wim; Dangreau, Ruben; Huvaere, Kevin; Gemoets, Hannes P. L.; Mottaghi, Milad; Kuhn, Simon; Van Aken, Koen. Safety of 4-Bromotetrahydropyran And the article was included in Organic Process Research & Development in 2020. The article conveys some information:

Continuous flow reactor technol. has a proven track record in enabling photochem. transformations. However, transfer of a photochem. batch process to a flow protocol often remains elusive, especially when solid reagents or catalysts are employed. In this work, application of an oscillatory plug flow photoreactor enabled a heterogeneous MacMillan-type C(sp2)-C(sp3) cross-electrophile coupling. Combination of an oscillatory flow regime with static mixing elements imparts exquisite control over the mixing intensity and residence time distribution, pinpointing a mindset shift concerning slurry handling in continuous flow reactors. The C(sp2)-C(sp3) cross-electrophile coupling was successfully transferred from batch to flow, resulting in an intensified slurry process with significantly reduced reaction time and increased productivity (0.87 g/h). After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Safety 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.Safety of 4-Bromotetrahydropyran

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

The author of 《Oxidative Addition to Palladium(0) Made Easy through Photoexcited-State Metal Catalysis: Experiment and Computation》 were Kancherla, Rajesh; Muralirajan, Krishnamoorthy; Maity, Bholanath; Zhu, Chen; Krach, Patricia E.; Cavallo, Luigi; Rueping, Magnus. And the article was published in Angewandte Chemie, International Edition in 2019. Formula: C5H9BrO The author mentioned the following in the article:

Visible-light induced, palladium catalyzed alkylations of α,β-unsaturated acids with unactivated alkyl bromides are described. A variety of primary, secondary, and tertiary alkyl bromides are activated by the photoexcited palladium metal catalyst to provide a series of olefins at room temperature under mild reaction conditions. Mechanistic studies and d. functional theory (DFT) studies suggest that a photoinduced inner-sphere mechanism is operative in which a barrierless, single-electron transfer oxidative addition of the alkyl halide to Pd0 is key for the efficient transformation.4-Bromotetrahydropyran(cas: 25637-16-5Formula: C5H9BrO) 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.Formula: C5H9BrO

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

In 2022,Turro, Raymond F.; Brandstatter, Marco; Reisman, Sarah E. published an article in Angewandte Chemie, International Edition. The title of the article was 《Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines》.Application of 25637-16-5 The author mentioned the following in the article:

The preparation of heterobenzylic amines, e.g., I [R1 = H, 4-Cl, 5-F, 6-Me, etc.; R2 = i-Pr, n-Bu, t-Bu, cyclopropyl, cyclobutyl, (R)-PhCHMe; R3 = H, Me, R4 = PhCH2; R3 = H, R4 = 4-ClC6H4CH2, 2,6-Me2C6H3CH2, etc.; R3R4 = (CH2)2X(CH2)2; X = CH2, O, CO, NBoc], by a Ni-catalyzed reductive cross-coupling between heteroaryl imines, e.g., II, and C(sp3) electrophiles R3R4CHX1 (X1 = Cl, Br, I, phthalimidyloxycarbonyl) is reported. This umpolung-type alkylation proceeds under mild conditions, avoids the pre-generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox-active ligand upon coordination to a low-valent Ni center. The resulting bis(2-imino)heterocycle·Ni complexes can engage in alkylation reactions with a variety of C(sp3) electrophiles, giving heterobenzylic amine products in good yields. After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Application of 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.Application of 25637-16-5

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

In 2019,Organic Process Research & Development included an article by Pomberger, Alexander; Mo, Yiming; Nandiwale, Kakasaheb Y.; Schultz, Victor L.; Duvadie, Rohit; Robinson, Richard I.; Altinoglu, Erhan I.; Jensen, Klavs F.. SDS of cas: 25637-16-5. The article was titled 《A Continuous Stirred-Tank Reactor (CSTR) Cascade for Handling Solid-Containing Photochemical Reactions》. The information in the text is summarized as follows:

Visible-light photoredox reactions have been demonstrated to be powerful synthetic tools to access pharmaceutically relevant compounds However, many photoredox reactions involve insoluble starting materials or products that complicate the use of continuous flow methods. By integrating a new solid-feeding strategy and a continuous stirred-tank reactor (CSTR) cascade, we realize a new solid-handling platform for conducting heterogeneous photoredox reactions in flow. Residence time distributions for single phase and solid particles characterize the hydrodynamics of the heterogeneous flow in the CSTR cascade. Silyl radical-mediated metallaphotoredox cross-electrophile coupling reactions with an inorganic base as the insoluble starting material demonstrate the use of the platform. Gram-scale synthesis is achieved in 13 h of stable operation. In the experiment, the researchers used many compounds, for example, 4-Bromotetrahydropyran(cas: 25637-16-5SDS of cas: 25637-16-5)

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.SDS of cas: 25637-16-5

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

In 2017,Li, Gang; Ma, Xingxing; Jia, Chunqi; Han, Qingqing; Wang, Ya; Wang, Junjie; Yu, Liuyang; Yang, Suling published 《Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides》.Chemical Communications (Cambridge, United Kingdom) published the findings.Category: tetrahydropyran The information in the text is summarized as follows:

Meta/ortho-selective CAr-H (di)alkylation reactions of azoarenes I (R = C6H5, 4-CH3C6H4, 4-ClC6H4, etc.; R1 = H, 4-CH3, 4-Br, etc.) have been achieved via [Ru(p-cymene)Cl2]2 catalyzed ortho-metalation using various types of alkyl bromides such as 3-bromopentane, bromocyclohexane, 2-bromo-2-methylpropane, etc. Particularly, dual meta-alkylation of azoarenes I and reduction offer an attractive strategy for the synthesis of meta-alkylanilines such as 3-(pentan-3-yl)aniline, 4-methyl-3-(pentan-3-yl)aniline, 4-bromo-3-(pentan-3-yl)aniline, etc. which are difficult to access via traditional aniline functionalization methods. After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Category: tetrahydropyran)

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.Category: tetrahydropyran

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

《Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation》 was written by Delcaillau, Tristan; Bismuto, Alessandro; Lian, Zhong; Morandi, Bill. Application In Synthesis of 4-Bromotetrahydropyran And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

A nickel-catalyzed aryl thioether metathesis was developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.4-Bromotetrahydropyran(cas: 25637-16-5Application In Synthesis of 4-Bromotetrahydropyran) 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.Application In Synthesis of 4-Bromotetrahydropyran

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

In 2019,Journal of the American Chemical Society included an article by Lovett, Gabrielle H.; Chen, Shuming; Xue, Xiao-Song; Houk, K. N.; MacMillan, David W. C.. Synthetic Route of C5H9BrO. The article was titled 《Open-Shell Fluorination of Alkyl Bromides: Unexpected Selectivity in a Silyl Radical-Mediated Chain Process》. The information in the text is summarized as follows:

Herein, author disclose a novel radical strategy for the fluorination of alkyl bromides via the merger of silyl radical-mediated halogen-atom abstraction and benzophenone photosensitization. Selectivity for halogen atom abstraction from alkyl bromides is observed in the presence of an electrophilic fluorinating reagent containing a weak N-F bond despite the predicted favorability for Si-F bond formation. To account for this surprising selectivity, preliminary mechanistic and computational studies were conducted, revealing that a radical chain mechanism is operative in which kinetic selectivity for Si-Br abstraction dominates due to a combination of polar effects and halogen atom polarizability in the transition state. This transition metal-free fluorination protocol tolerates a broad range of functional groups, including alcs., ketones, and aldehydes, which demonstrates the complementary nature of this strategy to existing fluorination technologies. This system has been extended to the generation of gem-difluorinated motifs, which are commonly found in medicinal agents and agrochems. The results came from multiple reactions, including the reaction of 4-Bromotetrahydropyran(cas: 25637-16-5Synthetic Route 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.Synthetic Route of C5H9BrO

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