Month: November 2022

Li, Yangyang published the artcileNickel-catalyzed migratory alkyl-alkyl cross-coupling reaction, Recommanded Product: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is Chemical Science (2020), 11(38), 10461-10464, database is CAplus and MEDLINE.

A migratory cross-coupling strategy, which can overcome this obstacle to access the desired cross-coupling products ArCH(R)(CH₂)_nCR¹R²R³ (Ar = Ph, 4-fluorophenyl, indol-3-yl, etc.; R = cyclopentyl, cyclohexyl, cycloheptyl, N-benzyl-piperidin-4-yl, 2-methyl-propan-1-yl; R¹ = H, D; R² = H, D; R³ = H; n = 0-3, 5), 1-cyclopentyl-indan, 1-cycloheptyl-indan, (1-cyclopentyl-3-methyl-pentyl)benzene was described. Accordingly, a selective migratory cross-coupling of two alkyl electrophiles (RBr, ArCH(R)(CH₂)_nCR¹R²R³ (R³ = Br or Cl), 2-bromoindan, (5-bromo-1-cyclopentyl-3-methyl-pentyl)benzene) has been accomplished by nickel catalysis. Remarkably, this alkyl-alkyl cross-coupling reaction provides a platform to prepare 2°-2° carbon-carbon bonds from 1° and 2° carbon coupling partners. Preliminary mechanistic studies suggest that chain-walking occurs at both alkyl halides in this reaction, thus a catalytic cycle with the key step involving two alkylnickel(II) species is proposed for this transformation.

Chemical Science published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, Recommanded Product: 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, Xin-Gang published the artcileRuthenium(II)-catalyzed selective C-H difluoroalkylation of aniline derivatives with pyrimidyl auxiliaries, Application In Synthesis of 401-55-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(68), 9541-9544, database is CAplus and MEDLINE.

A ruthenium-catalyzed alternative para- and meta-difluoroalkylation of anilines is herein reported. The reaction tolerates a broad range of aniline derivatives and provides a convenient approach for accessing the corresponding para/meta-selective difluoroalkylated products. Mechanism studies demonstrated that the initial C_Ar-H and N-H cycloruthenation is the pivotal step in achieving remote C-H difluoroacetylation.

Chemical Communications (Cambridge, United Kingdom) published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C12H10O4S, Application In Synthesis of 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, Xin-Gang published the artcileThree-Component Ruthenium-Catalyzed Direct Meta-Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes, Synthetic Route of 401-55-8, the publication is Journal of the American Chemical Society (2019), 141(35), 13914-13922, database is CAplus and MEDLINE.

Multicomponent reactions are fundamentally different from two-component reactions, as multicomponent reactions can enable the efficient and step-economical construction of complex mol. scaffolds from simple precursors. Here, an unprecedented three-component direct C-H addition was achieved in the challenging meta-selective fashion. Fluoroalkyl halides and a wide range of alkenes, including vinylarenes, unactivated alkenes, and internal alkenes, were employed as the coupling partners of arenes in this strategy. The detailed mechanism presented is supported by kinetic isotope studies, radical clock experiments, and d. functional theory calculations Moreover, this strategy provided access to various fluoride-containing bioactive 1,1-diarylalkanes and other challenging synthetically potential products.

Journal of the American Chemical Society published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C7H6Cl2, Synthetic Route of 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Lixin published the artcileFacial Syntheses of Bromobenzothiazines via Catalyst-Free Tandem C-H Amination/Bromination in Water, Application In Synthesis of 89694-44-0, the publication is Organic Letters (2019), 21(15), 5995-5999, database is CAplus and MEDLINE.

A transition-metal-free and environmentally friendly synthesis method for bromobenzothiazines through tandem C-H amination/bromination was reported. This reaction contains both intramol. C-H amination and site-selective electrophilic bromination of arenes with NaBr as the bromo source, PhI(OAc)₂ or K₂S₂O₈ as the oxidant, and H₂O as the only solvent.

Organic Letters published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Application In Synthesis of 89694-44-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yang, Wu published the artcileLewis acid-assisted Ir(III) reductive elimination enables construction of seven-membered-ring sulfoxides, Safety of (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, the publication is Chemical Science (2020), 11(37), 10149-10158, database is CAplus and MEDLINE.

Iridium has played an important role in the evolution of C-H activation chem. over the last half century owing to its high reactivity towards stoichiometric C-H bond cleavage; however, the use of Ir(III) complexes in catalytic C-H functionalization/C-C bond formation appears to have fallen off significantly. The main problem lies in the reductive elimination step, as iridium has a tendency to form stable and catalytically inactive Ir(III) species. Herein, with a rationally designed Lewis acid assisted oxidatively induced strategy, the sluggish Ir(III) reductive elimination is successfully facilitated, enabling the facile C-C bond formation. The X-ray crystal structure of a silver salt adduct of iridacycle and DFT calculations demonstrate that the sulfoxide group acts as a key bridge connecting the Ir(III) metal center with the silver Lewis acid, which facilitates the reductive elimination of the Ir(III) metallacycle. Further identification of oxidants was carried out by performing stoichiometric reactions, which enables the development of catalytic construction of various highly functionalized seven-membered-ring sulfoxides e.g., 5,7-dihydrodibenzo[c,e]thiepine 6-oxide, that are of great interest in medicinal chem. and materials science.

Chemical Science published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C23H20BN, Safety of (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Ding, Xiao published the artcileDe Novo Design, Synthesis and Evaluation of Benzylpiperazine Derivatives as Highly Selective Binders of Mcl-1, Recommanded Product: 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is ChemMedChem (2013), 8(12), 1986-2014, database is CAplus and MEDLINE.

Considerable efforts have been made towards the development of small-mol. inhibitors of antiapoptotic B-cell lymphoma 2 (Bcl-2) family proteins (such as Bcl-2, Bcl-x_L, and Mcl-1) as a new class of anticancer therapies. Unlike general inhibitors of the entire family, selective inhibitors of each member protein can hopefully reduce the adverse side effects in chemotherapy treatments of cancers overexpressing different Bcl-2 family proteins. In this study, we designed four series of benzylpiperazine derivatives as plausible Bcl-2 inhibitors based on the outcomes of a computational algorithm. A total of 81 compounds were synthesized, and their binding affinities to Bcl-2, Bcl-x_L, and Mcl-1 measured. Encouragingly, 22 compounds exhibited binding affinities in the micromolar range (K_i<20 μM) to at least one target protein. Moreover, some compounds were observed to be highly selective binders to Mcl-1 with no detectable binding to Bcl-2 or Bcl-x_L, among which the most potent one, I, has a K_i value of 0.18 μM for Mcl-1. Binding modes of four selected compounds to Mcl-1 and Bcl-x_L were derived through mol. docking and mol. dynamics simulations. It seems that the binding affinity and selectivity of these compounds can be reasonably interpreted with these models. Our study demonstrated the possibility for obtaining selective Mcl-1 inhibitors with relatively simple chem. scaffolds. The active compounds identified by us could be used as lead compounds for developing even more potent selective Mcl-1 inhibitors with potential pharmaceutical applications.

ChemMedChem published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Recommanded Product: 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Lu, Dengfu published the artcileCu-Catalyzed C_(sp3)-N Coupling and Alkene Carboamination Enabled by Ligand-Promoted Selective Hydrazine Transfer to Alkyl Radicals, Recommanded Product: Ethylbromofluoroacetate, the publication is ACS Catalysis (2022), 12(6), 3269-3278, database is CAplus.

In this work, di-tert-Bu hydrazodiformate was found to be a unique effective amination reagent in Cu-catalyzed C(sp³)-N bond formation reactions that involve alkyl radical intermediates. This method was applicable to both electron-deficient and electron-rich radicals, and were able to achieve the direct C-N coupling of activated bromides, as well as the carboamination of general alkenes based on this chem. Mechanistic studies suggested that the hydrazodiformate forms a reducing dinuclear complex with Cu and the ligand which, upon 1e-oxidation, turns into an open-shell species with the major spin d. on N atoms. With the assistance of a ligand, this species can selectively deliver the hydrazine moiety onto an alkyl radical (prior to halide transfer), leading to the formation of a C(sp³)-N bond. The products obtained with this amination method could be easily deprotected to afford alkyl hydrazines and further derived to primary amines or N-heterocycles.

ACS Catalysis published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Recommanded Product: Ethylbromofluoroacetate.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, Yan-en published the artcileSynthesis of Bisboronic Acids and Their Selective Recognition of Sialyl Lewis X Antigen, Category: bromides-buliding-blocks, the publication is Chemical Research in Chinese Universities (2018), 34(3), 415-422, database is CAplus.

The development of sensors that recognize Lewis oligosaccharides can help the diagnosis and early detection of cancer. Herein, authors reported the design and synthesis of a series of anthracene-based bisboronic acids (9a–9e) with different N-substituents near the boronic acid unit. Among them, compound 9a could recognize sialyl Lewis X(sLe^x) with selectivity over other Lewis sugars, and could significantly stain sLe^x-expressing HEPG2 cells with selectivity over the range of 0.1-10 μmol/L. Compound 9a possibly has two properly positioned boronic acids caused by the steric hindrance by the near N-benzyl substituent group, which empower its sLe^x selectivity and higher binding affinity.

Chemical Research in Chinese Universities published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C15H21BO2, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wang, Yaping published the artcileOne-Pot Double Benzylation of 2-Substituted Pyridines using Palladium-Catalyzed Decarboxylative Coupling of sp² and sp³ Carbons, Related Products of bromides-buliding-blocks, the publication is Advanced Synthesis & Catalysis (2014), 356(16), 3307-3313, database is CAplus.

An efficient and practical decarboxylative double benzylation method for various 2-picolinic acids has been established by using a bimetallic catalytic system of palladium(II) chloride (PdCl₂) and silver(I) oxide (Ag₂O), which offered a variety of diarylmethane derivatives e.g., I, with moderate to good yields.

Advanced Synthesis & Catalysis published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C15H14Cl2S2, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yang, Tangpo published the artcileA bifunctional amino acid to study protein-protein interactions, Name: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is RSC Advances (2020), 10(69), 42076-42083, database is CAplus and MEDLINE.

Protein-protein interactions (PPIs) play crucial roles in regulating essentially all cellular processes. Photo-crosslinking represents a powerful method to study PPIs. To fulfil the requirements for the exploration of different PPIs, there is a continuous demand on the development of novel photo-reactive amino acids with diverse structural properties and functionalities. Reported herein is the development of a bifunctional amino acid termed dzANA, which contains a diazirine, for photo-crosslinking, and a terminal alkyne group, for bioorthogonal tagging. Using known PPIs between histone posttranslational modifications (PTMs) and their binding partners as models, we demonstrate that the dzANA-harbouring peptide-based photoaffinity probes could efficiently and selectively capture the weak and transient PPIs mediated by histone modifications. Our study indicates the potential of dzANA to identify and characterize unknown PPIs.

RSC Advances published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C11H8F2, Name: (4-Bromobut-1-yn-1-yl)trimethylsilane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary