Category: 190788-60-4

Kwon, Yong-Ju; Kim, Won-Suk published the artcile< Protecting Group-Controlled Regioselective Synthesis for Unsymmetrical 3,5-Disubstituted Pyridones>, Related Products of 190788-60-4, the main research area is unsym disubstituted pyridone preparation regioselective; dibromo silyloxypyridine Suzuki Miyaura arylation deprotection.

Protecting group-controlled regioselective functionalization of 3,5-dibromo-2-pyridones has been studied for preparation of unsym. 3,5-disubstituted 2-pyridones. A bulky di-tert-butyl(isobutyl)silyl (BIBS) group was utilized for C5 regioselective arylation in Suzuki-Miyaura reactions. Meanwhile, the p-toluenesulfonyl (Ts) group was used to maximize C3 selective halogen-lithium exchange employing flow chem. Most of the reactions proceeded well, with yields of 76 to 95% and excellent regioselectivity. A one-pot synthesis of unsym. 3,5-diaryl-2-pyridones starting from 3,5-dibromo-2-silyloxypyridine was conducted to demonstrate the practical convenience. Further functionalization onto the remaining bromine group, such as transition metal-catalyzed C-C and C-N bond-forming reactions and retro-Brook rearrangement for C-Si bond formation, was accomplished for synthesis of biol. relevant 3,5-disubstituted 2-pyridones. Finally, amrinone and milrinone, commonly used for congestive heart failure, were synthesized in three steps from 3,5-dibromo-2-pyridones in 41% and 56% overall yields, resp.

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

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

Ling, Liang; He, Yuan; Zhang, Xue; Luo, Meiming; Zeng, Xiaoming published the artcile< Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene-Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles>, Computed Properties of 190788-60-4, the main research area is cyclic aminocarbene rhodium complex preparation catalyst hydrogenation heteroaryl boronate; crystal structure aminocyclohexylboronate ester cyclic aminocarbene rhodium complex; mol structure aminocyclohexylboronate ester cyclic aminocarbene rhodium complex; borylated cycloalkane preparation coupling arylation reaction; heterocycle cis borylated preparation; N-heterocyclic carbenes; boron; hydrogenation; selectivity; transition-metal catalysis.

The authors herein report the hydrogenation of substituted aryl- and heteroaryl boronate esters for the selective synthesis of cis-substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene-ligated Rh complex with two di-Me groups at the ortho-alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom-economic, as well as chemo- and stereoselective route for the generation of cis-configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare

Angewandte Chemie, International Edition published new progress about Aromatic compounds Role: CAT (Catalyst Use), RCT (Reactant), SPN (Synthetic Preparation), USES (Uses), RACT (Reactant or Reagent), PREP (Preparation) ((hetero)aryl boronate esters). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Computed Properties of 190788-60-4.

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

Dhakshinamoorthy, Amarajothi; Garcia, Cristina Valles; Concepcion, Patricia; Garcia, Hermenegildo published the artcile< Arene borylation through C-H activation using Cu3(BTC)2 as heterogeneous catalyst>, HPLC of Formula: 190788-60-4, the main research area is arene borylation carbon hydrogen activation copper MOF catalyst mechanism.

C-H borylation by diborane is an important process to access organoboron compounds Noble metals, including Ir and Rh-based complexes either in the form of homogeneous or heterogeneous catalysts, have been reported to promote arene C-H borylation. Recently, metal organic frameworks (MOFs) having Ir and Co as active sites have been used as catalysts, but they require co-catalysts. In the present study, com. available Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) MOF is reported as an effective catalyst to promote borylation of arenes through C-H activation employing bis(pinacolato)diboron as reagent leading to benzylic and aromatic borylation products. Interestingly, other related MOFs like MIL-101(Cr) and Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylate) do not exhibit catalytic activity under identical conditions. Mechanistic studies using in-situ IR spectroscopy reveal that Cu ions play a crucial role in activating the arene and B-B bond in bis(pinacolato)diboron.

Catalysis Today published new progress about Aromatic hydrocarbons Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, HPLC of Formula: 190788-60-4.

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

Bhatthula, Bharath Kumar Goud; Kanchani, Janardhan Reddy; Arava, Veera Reddy; Subha, M. C. S. published the artcile< Total synthesis of carbazole alkaloids>, Reference of 190788-60-4, the main research area is carbazole alkaloid total synthesis Suzuki Miyaura cross coupling; Cadogan reductive cyclization total synthesis carbazole alkaloid.

A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid Me ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives

Tetrahedron published new progress about Cadogan reaction. 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

Mizoguchi, Haruki; Seriu, Masaya; Sakakura, Akira published the artcile< Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate>, Category: ethers-buliding-blocks, the main research area is crystal structure mol optimized seleno cyclopropyl boronic ester preparation; stereoselective metalate rearrangement cyclopropenyl boronate.

A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metalate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metalate rearrangement suggested that the reaction proceeds through a seleniranium intermediate.

Chemical Communications (Cambridge, United Kingdom) published new progress about Boronic acids, esters Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (cyclopropyl). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Category: ethers-buliding-blocks.

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

Haydl, Alexander M.; Hartwig, John F. published the artcile< Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters>, Quality Control of 190788-60-4, the main research area is palladium catalyzed methylation aryl heteroaryl boronate ester iodomethane; methylated arene heterocycle preparation palladium catalyzed methylation.

A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biol. active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.

Organic Letters published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation) (methylated). 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

Wang, Peng; Chen, Shuqing; Zhou, Zhiyu; Cheng, Hong-Gang; Zhou, Qianghui published the artcile< Chemoselective Borono-Catellani Arylation for Unsymmetrical Biaryls Synthesis>, Quality Control of 190788-60-4, the main research area is biaryl alkene alkenoate chemoselective diastereoselective preparation; palladium norbornenedicarboxylate catalyst borono Catellani reaction; chemoselective stereoselective arylation arylpinacolboronate bromoarene alkene palladium norbornenedicarboxylate catalyst.

In the presence of Pd(OAc)2 and a norbornenedicarboxylate, arylpinacolboronates such as 2-methylphenyl pinacolboronate underwent chemoselective aerobic borono-Catellani reactions with aryl bromides such as Me 2-bromobenzoate and alkenes (including α,β-unsaturated esters) such as tert-Bu acrylate to yield unsym. biaryl alkenes such as biphenylpropenoate I. In the absence of alkene, a bromophenylcarbamate underwent coupling and cyclization with 2-naphthylpinacolboronate to yield a mixture of benzocarbazoles in 45% combined yield; a bromophenol underwent coupling without cyclization.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Marx, Lisa; Lamberty, Daniel; Choppin, Sabine; Colobert, Francoise; Speicher, Andreas published the artcile< Atroposelective Synthesis of Isoriccardin C through a C-H Activated Heck Type Macrocyclization>, Recommanded Product: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the main research area is atroposelective synthesis isoriccardin C carbon hydrogen activated Heck macrocyclization.

Macrocyclization is typically the key step in syntheses of cyclophane-type natural products. Considering compounds with axially chiral biaryl moieties, the control of atroposelectivity is essential for biol. activity and is synthetically challenging. Herein we report on atroposelective macrocyclization involving an oxidative Heck type process and enabling the first atropo-enantiopure synthesis of (P)-isoriccardin C (I). A chiral sulfinyl auxiliary in the ortho-position of a biaryl axis (still flexible) was used to induce a C-H activated atropodiastereoselective oxidative Heck coupling (>98% de). The traceless character of the sulfinyl auxiliary enables the introduction of a hydroxy group to give the target mol. with >98% ee as well.

European Journal of Organic Chemistry published new progress about Atropisomers. 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

Wright, Jay S.; Sharninghausen, Liam S.; Preshlock, Sean; Brooks, Allen F.; Sanford, Melanie S.; Scott, Peter J. H. published the artcile< Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes>, Product Details of C13H19BO3, the main research area is sequential iridium copper mediated regioselective radiofluorination arene heteroarene.

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochem. yield and radiochem. purity. This entire process is performed on a bench top without Schlenk or glove box techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochem. yield and >99% radiochem. purity and 25% isolated radiochem. yield and 99% radiochem. purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), resp.

Journal of the American Chemical Society published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Evans, Kieren J.; Morton, Paul A.; Luz, Christian; Miller, Callum; Raine, Olivia; Lynam, Jason M.; Mansell, Stephen M. published the artcile< Rhodium Indenyl NHC and Fluorenyl-Tethered NHC Half-Sandwich Complexes: Synthesis, Structures and Applications in the Catalytic C-H Borylation of Arenes and Alkanes>, Name: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the main research area is rhodium indenyl fluorenyl half sandwich NHC imidazolylidene complex preparation; alkene carbonyl rhodium half sandwich NHC complex preparation photodissociation; borylation catalyst rhodium half sandwich NHC arylboronate alkylboronate preparation; CH activation aromatic aliphatic hydrocarbon borylation rhodium catalyst; crystal mol structure rhodium NHC alkene carbonyl half sandwich; C−H activation; C−H borylation; Rh N-heterocyclic carbene catalysts; rhodium indenyl; tethered NHC.

Indenyl (Ind) rhodium N-heterocyclic carbene (NHC) complexes [Rh(η5-Ind)(NHC)(L)] [NHC = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene (SIPr); 1, 2a, 3, L = C2H4, CO, cyclooctene (COE); NHC = 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene (SIMes); 2b, 4, L = CO, COE; NHC = 1,3-dimesitylimidazol-2-ylidene (IMes); 2c, 5, L = CO, COE]. Reaction of SIPr with [Rh(Cp*)(C2H4)2] did not give the desired SIPr complex, thus demonstrating the “”indenyl effect”” in the synthesis of 1. Oxidative addition of HSi(OEt)3 to 3 proceeded under mild conditions to give the Rh silyl hydride complex [Rh(Ind)[Si(OEt)3](H)(SIPr)] (6) with loss of COE. Ethylene-tethered-fluorenyl NHC rhodium complexes [Rh[(η5-C13H8)-9-C2H4NC2Hx(C:)NR](L)] (x = 4, R = Dipp: 11, L = C2H4; 12, L = COE; 13, L = CO; x = 4, R = Mes: 14, L = COE; 15, L = CO; x = 2, R = Me: 16, L = COE; 17, L = CO) were synthesized in low yields (5-31%) in comparison to good yields for the monodentate complexes (49-79%). Compounds 3 and 1, which contain labile alkene ligands, were successful catalysts for the catalytic borylation of benzene with B2pin2 (Bpin = pinacolboronate), giving yields of 97% and 93% of PhBpin resp. with 5 mol% catalyst, 24 h, 80°, with SIPr giving a more active catalyst than SIMes or IMes. Fluorenyl-tethered NHC complexes were much less active as borylation catalysts, and the carbonyl complexes were inactive. The borylation of toluene, biphenyl, anisole and di-Ph ether proceeded to give meta substitutions as the major product, with smaller amounts of para substitution and almost no ortho product. The borylation of octane and decane with B2pin2 at 120 and 140°, resp., was monitored by 11B NMR spectroscopy, which showed high conversions into octyl and decylBpin over 4-7 days, thus demonstrating catalyzed sp3 C-H borylation with new piano stool rhodium indenyl complexes. Irradiation of the monodentate complexes with 400 or 420 nm light confirmed the ready dissociation of C2H4 and COE ligands, whereas CO complexes were inert. Evidence for C-H bond activation in the alkyl groups of the NHC ligands was obtained.

Chemistry – A European Journal published new progress about Boronic acids, esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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