Category: 190788-60-4

Antuganov, Dmitrii; Zykov, Michail; Timofeev, Vasilii; Timofeeva, Ksenija; Antuganova, Yulija; Orlovskaya, Victoriya; Fedorova, Olga; Krasikova, Raisa published the artcile< Copper-Mediated Radiofluorination of Aryl Pinacolboronate Esters: A Straightforward Protocol by Using Pyridinium Sulfonates>, Electric Literature of 190788-60-4, the main research area is aryl pinacolboronate ester radiofluorination copper pyridinium sulfonate catalyst base.

Radiofluorination of arylboronic acids pinacol esters (arylBPin) mediated by copper triflate pyridine complex is one of the more promising synthetic approaches for the direct introduction of nucleophilic [18F]fluoride into non-activated arenes and heteroarenes. However, the application of this method to the production of positron emission tomog. (PET) radiotracers in automated synthesizers remains a challenging task. The choice of phase-transfer catalyst (PTC) and corresponding base used for the generation of reactive [18F]fluoride species has a profound impact on the efficiency of the 18F-fluorination process. Herein the authors report the development of a simple procedure involving trapping of the aqueous [18F]fluoride on a weak anion-exchange resin (WAX) and its release by elution with pyridinium sulfonate in di-Me acetamide. Obtained reactive [18F]fluoride was used as-is in a copper-catalyzed fluorination reaction employing pyridinium salt as both PTC and base. High radiochem. conversion rates (RCCs) achieved for a series of simple arylBPin substrates and 4-[18F]fluoro-D,L-phenylalanine demonstrate the efficiency of this novel 18F-processing approach. Notably, the proposed method obviates conventional azeotropic drying steps, solvents evaporation and/or changeover and can be implemented on com. automated synthesizers.

European Journal of Organic Chemistry published new progress about Esters Role: RCT (Reactant), RACT (Reactant or Reagent) (Aryl Pinacolboronate Esters). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Electric Literature of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Tang, Huiling; Liu, Mengna; Zhu, Meiqi; Cui, Benqiang; Shi, Yanhui; Cao, Changsheng published the artcile< C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd-NHC complex>, SDS of cas: 190788-60-4, the main research area is phenylnaphthalene preparation; arylammonium salt phenylboronic acid Suzuki cross coupling palladium catalyst.

The authors developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C-N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid and pinacol ester or anhydride and provided biaryls Ar1-Ar2 [Ar1 = 1-naphthyl, Ph, 2-pyridyl, etc., Ar2 = Ph, 4-MeC6H4, 4-PhC6H4, etc.] in up to 97% yield with good functional group compatibility. The direct arylation of arylamine could be performed by a two-step, one-pot process and a protocol could be performed on the gram scale.

Tetrahedron published new progress about Biaryls Role: SPN (Synthetic Preparation), PREP (Preparation). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, SDS of cas: 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Xu, Jinhui; Cao, Jilei; Wu, Xiangyang; Wang, Han; Yang, Xiaona; Tang, Xinxin; Toh, Ren Wei; Zhou, Rong; Yeow, Edwin K. L.; Wu, Jie published the artcile< Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides>, Product Details of C13H19BO3, the main research area is aryl chloride boronate light cyanoarene photoreductive borylation catalyst; arylboronate preparation; phosphine aryl chloride light cyanoarene phosphorylation catalyst; arylphosphonium salt preparation.

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN•-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.

Journal of the American Chemical Society published new progress about Aromatic nitriles Role: CAT (Catalyst Use), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Product Details of C13H19BO3.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Yamaoka, Yousuke; Yamakawa, Takuro; Tateishi, Kaito; Takasu, Kiyosei published the artcile< Total Synthesis of Cryptopleurine and Its Analogues>, SDS of cas: 190788-60-4, the main research area is total synthesis cryptopleurine analog.

Total synthesis of phenanthroquinolizidine alkaloid (±)-cryptopleurine (I) was achieved in 8 steps from com. available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.

Synthesis published new progress about Oxidative coupling reaction (oxidative biaryl coupling). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, SDS of cas: 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Varni, Anthony J.; Bautista, Michael V.; Noonan, Kevin J. T. published the artcile< Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes Under Mild Conditions>, Reference of 190788-60-4, the main research area is rhodium catalyst chemoselective borylation bromoiodoarene preparation bromoaryl boronate; aryl bromide boronate trifluoroborate preparation Suzuki coupling polymerization substrate.

A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Addnl., the reaction’s utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.

Journal of Organic Chemistry published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Reference of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Chen, Yixuan; Gu, Yuefei; Meng, Huan; Shao, Qianzhen; Xu, Zhenchuang; Bao, Wenjing; Gu, Yucheng; Xue, Xiao-Song; Zhao, Yanchuan published the artcile< Metal-Free C-H Functionalization via Diaryliodonium Salts with a Chemically Robust Dummy Ligand>, Recommanded Product: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the main research area is unsym iodonium salt preparation; Cross-Coupling; C−H Functionalization; Diaryliodonium Salts; Hypervalent Compounds; Structural Diversification.

A two-step strategy for the transition-metal-free C-H functionalization of arenes using unsym. iodonium salts as versatile synthetic linchpins was presented. The key to the success of this strategy was the identification of the 3,5-dimethyl-4-isoxazolyl (DMIX) group as a superior dummy ligand, which enabled not only site-selective C-H functionalization to afford unsym. iodonium salts I [R = Ph, 2-thienyl, 3,4-di-ClC6H4, etc.; X = OAc, OTs], but also highly selective aryl transfer during the subsequent metal-free coupling reaction. Both electron-rich and moderately electron-deficient arenes could be converted into the iodonium salts through C-H functionalization, allowing for diverse structural elaboration by metal-free C-N, C-C, C-S, and C-O coupling.

Angewandte Chemie, International Edition published new progress about C-H bond activation. 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Recommanded Product: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Li, Yafei; Dang, Yan; Li, Dawei; Pan, Huifen; Zhang, Liang; Wang, Li; Cao, Zhu; Li, Yahong published the artcile< Zinc Complexes with an Ethylene-Bridged Bis(β-diketiminate) Ligand: Syntheses, Structures, and Applications as Catalysts in the Borylation of Aryl Iodides>, Application In Synthesis of 190788-60-4, the main research area is crystal structure mol zinc complex ethylene bridged bisdiketiminate complex; zinc complex ethylene diketiminate preparation borylation catalyst aryl iodide.

A dinucleating bis(β-diketiminate) ligand with a flexible bridge has been employed to synthesize zinc complexes. The ligand, abbreviated H2L (H2L = N-(4-((2-((4-((2,6-diisopropylphenyl)imino)pent-2-en-2-yl)amino)ethyl)imino)pent-2-en-2-yl)-2,6-diisopropylaniline), was deprotonated with ZnEt2 to afford [LZn2Et2] (1). Reactions of 1 with 2 equiv of BnOH and nBuOH, resp., gave access to [LZn2(OBn)2]·C6H14 (2·C6H14) and [LZn2(OnBu)2] (3). Treatment of 1 with 2 equiv of I2 in THF produced [LZn2I2(THF)2]·2THF (4·2THF). X-ray single-crystal diffraction analyses revealed that they are all heteroleptic bimetallic compounds with two metal centers being chelated by one ligand set. The structurally similar compounds 1 and 4·2THF possess approx. C2 symmetry, with two β-diketiminate units being arrayed in head-to-tail antiparallel mode. Thus, the mol. structures of 1 and 4·2THF exhibit a seesaw-like topol. The structures of 2·C6H14 and 3 are almost identical, in which two zinc atoms are shared by two ZnN2C3 six-membered rings, two Zn2ON2C2 seven-membered rings, and one Zn2O2 four-membered ring. Therefore, the metal cores of 2·C6H14 and 3 display a crownlike topol. All complexes are catalytically active for the borylation of aryl iodides with B2Pin2 (B2Pin2 = 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane)). Complex 1 shows higher activity in comparison to 2, 3, and 4·2THF. The borylation reactions catalyzed by 1 could proceed under mild conditions and can be applied to a series of substrates with high functional group generality. This methodol. thus represents a novel use of β-diketiminate zinc complexes for C-I borylation.

Organometallics published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Application In Synthesis of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhang, Liang; Li, Yafei; Wang, Li; Cao, Zhu; Zhang, Qian; Li, Yahong published the artcile< Two β-Diketiminate Zinc Complexes with 1-D Chain and Dinuclear Topologies: Synthesis, Structures, and Catalytic Behavior>, SDS of cas: 190788-60-4, the main research area is preparation zinc diketiminate complex borylation catalyst aryl iodide.

Two zinc complexes, [L1Zn2Et2]n (1) and [L2Zn2Et2] (2), were synthesized by reacting bis(β-diketiminate) ligands H2L1 and H2L2 with ZnEt2. X-ray single-crystal diffraction anal. indicated that compound 1 displays a novel 1-dimensional chain structure. Compound 2 is dinuclear. The two compounds were employed to catalyze the coupling reaction of aryl iodides with B2Pin2. They were both catalytically active toward this transformation. Compound 1 exhibited higher catalytic activity than that of complex 2. The borylation reactions catalyzed by 1 possess the features of milder conditions, high functional group tolerance and wide range of substrate scopes.

European Journal of Inorganic Chemistry published new progress about Aryl iodides Role: RCT (Reactant), RACT (Reactant or Reagent). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, SDS of cas: 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Chen, Qiaoyu; Li, Sanliang; Xie, Xiaoxiao; Guo, Hao; Yang, Junfeng; Zhang, Junliang published the artcile< Pd-Catalyzed Enantioselective Dicarbofunctionalization of Alkene to Access Disubstituted Dihydroisoquinolinone>, Name: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the main research area is asym Heck Suzuki domino alkene hydroisoquinolinone synthesis.

A Pd/Xu-Phos-catalyzed asym. Heck/Suzuki domino reaction has been developed that shows high functional group tolerance and enables coupling with various aryl/alkenyl borates. A series of chiral disubstituted dihydroisoquinolinones could be obtained in good yields and excellent enantioselectivities.

Organic Letters published new progress about Benzamides Role: RCT (Reactant), RACT (Reactant or Reagent). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Name: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhu, You-Quan; Hui, Li-Wen; Niu, Yun-Xia; Lv, Lin-Ge; Zhu, Kun published the artcile< Reaction of Cycloalkene-1-carboxamides with Aryl Boronates via Rhodium(III)-Catalyzed C-H Activation: A Versatile Route to 3,4-Cycloalkaquinolin-2(1H)-ones>, Quality Control of 190788-60-4, the main research area is cycloalkaquinolinone preparation; methoxycycloalkene carboxamide arylboronic acid pinacol ester heterocyclization rhodium catalyst.

Under rhodium(III) catalysis, substituted N-methoxycycloalkene-1-carboxamides I [X = CH2, O; Z = a bond, CH2; Y = CH2, N-C(O)OC(CH3)3; R1 = H, prop-1-en-2-yl] successfully reacted with aryl boronic acid pinacol esters II (R2 = 3-F, 4-C6H5O, 4-H3CO, etc.) to provide 3,4-cycloalkaquinolin-2(1H)-ones III (R3 = 9-F, 8-C6H5O, 8-H3CO, etc.) via direct functionalization of the β-alkenyl C-H bond and form C-C/C-N bond in one pot. The gram-scale synthesis of the title compound III (X = CH2; n = 1; Y = CH2; R1 = H; R3 = H) demonstrated the great synthetic utility of this methodol.

Advanced Synthesis & Catalysis published new progress about Amides Role: RCT (Reactant), RACT (Reactant or Reagent) (cycloalkene). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Quality Control of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem