Tag: M.W=250-300

Hilton, Margaret J.; Cheng, Bin; Buckley, Benjamin R.; Xu, Liping; Wiest, Olaf; Sigman, Matthew S. published the artcile< Relative reactivity of alkenyl alcohols in the palladium-catalyzed redox-relay Heck reaction>, Safety of (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is reactivity alkenyl alc palladium catalyzed relay Heck; Heck reaction; competition experiments; redox-relay; relative rates of alkenes.

The relative rates of alkenyl alcs. in the Pd-catalyzed redox-relay Heck reaction were measured to examine the effect of their steric and electronic properties on the rate-determining step. Competition experiments between an allylic alkenyl alc. and two substrates with differing chain lengths revealed that the allylic alc. reacts 3-4 times faster in either case. Competition between di- and trisubstituted alkenyl alcs. provided an interesting scenario, in which the disubstituted alkene was consumed first followed by reaction of the trisubstituted alkene. Consistent with this observation, the transition structures for the migratory insertion of the aryl group into the di- and trisubstituted alkenes were calculated with a lower barrier for the former. An internal competition between a substrate containing two alcs. with differing chain lengths demonstrated the catalyst’s preference for migrating toward the closest alc. Addnl., increasing the electron-d. in the arene boronic acid promotes a faster reaction, which correlates with Hammett σp values to give a ρ of -0.87.

Tetrahedron published new progress about Alkenyl alcohols Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), PROC (Process), RACT (Reactant or Reagent), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Safety of (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Jiang, Ze-Zhen; Gao, Ang; Li, Hao; Chen, Di; Ding, Chang-Hua; Xu, Bin; Hou, Xue-Long published the artcile< Enantioselective Synthesis of Chromenes via a Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction>, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is chromene enantioselective synthesis palladium catalyzed Heck redox relay; Heck reaction; asymmetric catalysis; boronic acids; chromenes; palladium.

A palladium-catalyzed asym. redox-relay Heck reaction of 4H-chromenes and arylboronic acids has been successfully developed. The reaction proceeded in moderate to good yields with good to high enantioselectivities. The resulting product is an advanced intermediate of bio-active compound BW683C.

Chemistry – An Asian Journal published new progress about Arylboronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tian, Zhi-Xiong; Qiao, Jin-Bao; Xu, Guang-Li; Pang, Xiaobo; Qi, Liangliang; Ma, Wei-Yuan; Zhao, Zhen-Zhen; Duan, Jicheng; Du, Yun-Fei; Su, Peifeng; Liu, Xue-Yuan; Shu, Xing-Zhong published the artcile< Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes>, Safety of (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is enantioselective electrophile aryl alkenylation unactivated alkene.

Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, the authors report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biol. important chiral mols. such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can increases mol. diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand was used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex mols. such as peptides, indometacin, and steroids.

Journal of the American Chemical Society published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Safety of (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Yuan, Qianjia; Sigman, Matthew S. published the artcile< Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams>, Related Products of 1416819-91-4, the main research area is oxidative relay Heck arylation arylboronic acid lactam; substituted lactam asym preparation.

In this Communication, the construction of chiral α,β-unsaturated δ-lactams, e.g. I, widely used as pharmacophores, in high yields and excellent enantioselectivities using an oxidative relay Heck arylation reaction is reported. This strategy also allows facile access to 7-substituted α,β-unsaturated ε-lactam products and δ-lactams containing a tetrasubstituted nitrogen-bearing stereocenter.

Journal of the American Chemical Society published new progress about Arylboronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Related Products of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Patel, Harshkumar H.; Prater, Matthew B.; Squire, Scott O.; Sigman, Matthew S. published the artcile< Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers>, Quality Control of 1416819-91-4, the main research area is chiral allylic aryl ether preparation palladium catalyzed alkenylation; enantioselective palladium catalyzed alkenylation acyclic enol ether.

This report details a palladium-catalyzed process to access highly functionalized, optically active allylic aryl ethers. A number of electron-deficient alkenyl triflates underwent enantioselective and site-selective coupling with acyclic aryl enol ethers in the presence of a chiral palladium catalyst. This transform provides chiral allylic ether products in high yields and excellent enantiomeric ratios, furnishing a unique disconnection to incorporate heteroatoms at a stereocenter. Finally, the applicability of the products to target synthesis was demonstrated through the formation of a chiral allylic alc. and the generation of a flavone-inspired product.

Journal of the American Chemical Society published new progress about Alkenylation. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Quality Control of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lamb, Claire J. C.; Nderitu, Bryan G.; McMurdo, Gemma; Tobin, John M.; Vilela, Filipe; Lee, Ai-Lan published the artcile< Auto-Tandem Catalysis: PdII-Catalysed Dehydrogenation/Oxidative Heck Reaction of Cyclopentane-1,3-diones>, Category: pyridine-derivatives, the main research area is cyclopentanedione continuous flow preparation autocatalyzed dehydrogenation oxidative Heck coupling; aerobic oxidation; auto-tandem catalysis; one-pot synthesis; oxidative Heck; palladium.

A Pd(II) catalyst system has been used to successfully catalyze two mechanistically distinct reactions in a one-pot procedure: dehydrogenation of 2,2-disubstituted cyclopentane-1,3-diones and the subsequent oxidative Heck coupling. This auto-tandem catalytic reaction is applicable to both batch and continuous flow processes, with the latter being the first example of a tandem aerobic dehydrogenation/oxidative Heck in flow. In addition, a telescoped reaction involving enantioselective desymmetrization of the all-C quaternary center was successfully achieved.

Chemistry – A European Journal published new progress about Cyclopentanes Role: SPN (Synthetic Preparation), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pan, Qi; Ping, Yuanyuan; Wang, Yifan; Guo, Ya; Kong, Wangqing published the artcile< Ni-Catalyzed Ligand-Controlled Regiodivergent Reductive Dicarbofunctionalization of Alkenes>, Formula: C13H15F3N2O, the main research area is nickel catalyzed ligand controlled regiodivergent reductive dicarbofunctionalization alkene; five six membered benzo fused lactam preparation alkene dicarbofunctionalization; cyclization cross coupling indoleone dihydroquinolinone preparation.

Transition-metal-catalyzed dicarbofunctionalization of alkenes involving intramol. Heck cyclization followed by intermol. cross-coupling has emerged as a powerful engine for building heterocycles with sterically congested quaternary carbon centers. However, only exo-cyclization/cross-coupling products can be obtained; endo-selective cyclization/cross-coupling has not been reported yet and still poses a formidable challenge. We herein report the first example of catalyst-controlled dicarbofunctionalization of alkenes for the regiodivergent synthesis of five- and six-membered benzo-fused lactams bearing all-carbon quaternary centers. Using a chiral Pyrox- or Phox-type bidentate ligand, 5-exo cyclization/cross-couplings proceed favorably to produce indole-2-ones in good yields with excellent regioselectivity and enantioselectivities (up to 98% ee). When C6-carboxylic acid-modified 2,2′-bipyridine was used as the ligand, 3,4-dihydroquinolin-2-ones were obtained in good yields through 6-endo-selective cyclization/cross-coupling processes. This transformation is modular and tolerant of a variety of functional groups. The ligand rather than the substrate structures precisely dictates the regioselectivity pattern. Moreover, the synthetic value of this regiodivergent protocol was demonstrated by the preparation of biol. relevant mols. and structural scaffolds.

Journal of the American Chemical Society published new progress about Alkenylation. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Jiang, Xiaoli; Han, Bo; Xue, Yuhang; Duan, Mei; Gui, Zhuofan; Wang, You; Zhu, Shaolin published the artcile< Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes>, Category: pyridine-derivatives, the main research area is benzylic alkyne preparation regioselective chemoselective; alkene bromoalkyne migratory hydroalkynation nickel catalyst; chiral benzylic alkyne preparation chemoselective enantioselective; styrene bromoalkyne hydroalkynation nickel catalyst.

Here, an NiH-catalyzed reductive migratory hydroalkynation of olefins such as, 4-phenyl-1-butene, (E)-1,2-diphenylethene, 1H-indene, etc. with bromoalkynes RCCBr [R = tris(propan-2-yl)silyl, triphenylmethyl, tert-butyldiphenylsilyl] that delivers the corresponding benzylic alkynation products ArCH(CH2R1)CCR [Ar = Ph, naphthalen-2-yl, thiophen-3-yl, etc.; R1 = H, Et, 2-cyclohexylethyl, Ph, etc.] in high yields with excellent regioselectivities was reported. Catalytic enantioselective hydroalkynation of styrenes (E/Z)-Ar1CH=CHR2 [Ar1 = Ph, 2-methoxyphenyl, thiophen-3-yl, etc.; R2 = H, Me, Et, Ph, etc.] has also been realized using a simple chiral PyrOx ligand. The obtained enantioenriched benzylic alkynes (S)-Ar1CH(CH2R2)CCR [R = tris(propan-2-yl)silyl, triethylsilyl, tert-butyldimethylsilyl, etc.] are versatile synthetic intermediates and can be readily transformed into synthetically useful chiral synthons.

Nature Communications published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Yuan, Qianjia; Prater, Matthew B.; Sigman, Matthew S. published the artcile< Enantioselective Synthesis of γ-Functionalized Cyclopentenones and β-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy>, Electric Literature of 1416819-91-4, the main research area is gamma functionalized cyclopentenone enantioselective preparation; cyclopentenone aryl boronic acid alkenyl triflate palladium relay Heck; delta functionalized cycloheptenone enantioselective preparation; cycloheptenone aryl boronic acid alkenyl triflate palladium relay Heck; Asymmetric Catalysis; C–C Coupling; Heck Reaction; Palladium.

In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives was described. This method granted facile access to diverse γ-functionalized cyclopentenones I [Ar = Ph, 2-naphthyl, benzo[d][1,3]dioxol-5-yl, 4-oxocyclopent-2-en-1-yl, etc.] and δ-functionalized cycloheptenones II [R = Ph, 4-CF3C6H4, C(Me):C(Me)CO2Et, etc.]. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity.

Advanced Synthesis & Catalysis published new progress about Alkylation catalysts. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Electric Literature of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem