Wang, Zhaobin’s team published research in Nature Chemistry in 2021-03-31 | 1428537-19-2

Nature Chemistry published new progress about Alkenylation catalysts, stereoselective. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Category: pyridine-derivatives.

Wang, Zhaobin; Yang, Ze-Peng; Fu, Gregory C. published the artcile< Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides>, Category: pyridine-derivatives, the main research area is nickel catalytic enantioconvergent nucleophilic substitution tertiary alkyl electrophiles alkenylzirconium.

The development of efficient methods, particularly catalytic and enantioselective processes, for the construction of all-carbon quaternary stereocentres is an important (and difficult) challenge in organic synthesis due to the occurrence of this motif in a range of bioactive mols. One conceptually straightforward and potentially versatile approach is the catalytic enantioconvergent substitution reaction of a readily available racemic tertiary alkyl electrophile by an organometallic nucleophile; however, examples of such processes are rare. Here we demonstrate that a nickel-based chiral catalyst achieves enantioconvergent couplings of a variety of tertiary electrophiles (cyclic and acyclic α-halocarbonyl compounds) with alkenylmetal nucleophiles to form quaternary stereocentres with good yield and enantioselectivity under mild conditions in the presence of a range of functional groups. These couplings, which probably proceed via a radical pathway, provide access to an array of useful families of organic compounds, including intermediates in the total synthesis of two natural products, (-)-eburnamonine and madindoline A.

Nature Chemistry published new progress about Alkenylation catalysts, stereoselective. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

He, Yu-Ping’s team published research in Angewandte Chemie, International Edition in 2021-03-29 | 1416819-91-4

Angewandte Chemie, International Edition published new progress about Addition reaction, aminopalladation. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

He, Yu-Ping; Cao, Jian; Wu, Hua; Wang, Qian; Zhu, Jieping published the artcile< Catalytic Enantioselective Aminopalladation-Heck Cascade>, Application In Synthesis of 1416819-91-4, the main research area is alkynylaniline cyclopentene diastereoselective enantioselective palladium pyrox aminopalladation Heck cascade; indole cyclopentene stereoselective preparation; asymmetric synthesis; domino reactions; homogeneous catalysis; nucleopalladation; oxidative Heck reactions.

Domino processes initiated by intramol. nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains scarce. We report herein that reaction of 2-alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc)2, a chiral bidentate pyrox ligand and O2 as terminal oxidant affords the structurally diverse indole-cyclopentene conjugates, e.g., I, bearing two stereocenters in a highly diastereo- and enantio-selective manner. One of the products is converted to a heavily functionalized tetracyclic indolinone derivative

Angewandte Chemie, International Edition published new progress about Addition reaction, aminopalladation. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Xu, Si-Yu’s team published research in Organic & Biomolecular Chemistry in 2021 | 1416819-91-4

Organic & Biomolecular Chemistry 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.

Xu, Si-Yu; Zhang, Rui; Zhang, Shu-Sheng; Feng, Chen-Guo published the artcile< Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction>, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is arylphthalide preparation enantioselective nickel catalyst; bromophthalide arylboronic acid Suzukimiiyaura crosscoupling reaction.

A nickel-catalyzed asym. Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.

Organic & Biomolecular Chemistry 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

Chen, Zhi-Min’s team published research in Chemical Science in 2019 | 1416819-91-4

Chemical Science published new progress about Alkenyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application of C13H15F3N2O.

Chen, Zhi-Min; Liu, Jianbo; Guo, Jing-Yao; Loch, Maximillan; DeLuca, Ryan J.; Sigman, Matthew S. published the artcile< Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives>, Application of C13H15F3N2O, the main research area is alkenylarene alkenyl triflate palladium catalyst regioselective enantioselective Heck reaction.

A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters was disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provided rapid access to enantioenriched δ, ε, ζ and η-alkenyl aryl compounds from simple starting materials. Mechanistic studies suggested that termination of the relay reaction was controlled by affinity of the arene for the Pd complex during migration.

Chemical Science published new progress about Alkenyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application of C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Guo, Jing-Yao’s team published research in ACS Catalysis in 2017-06-02 | 1416819-91-4

ACS Catalysis published new progress about Bond angle, torsional. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

Guo, Jing-Yao; Minko, Yury; Santiago, Celine B.; Sigman, Matthew S. published the artcile< Developing Comprehensive Computational Parameter Sets To Describe the Performance of Pyridine-Oxazoline and Related Ligands>, Application In Synthesis of 1416819-91-4, the main research area is oxazoline pyridine quinoline ligand computational parameter set catalytic performance.

The applicability of computational descriptors extracted from metal pyridine-oxazoline complexes to relate both site and enantioselectivity to structural diversity was investigated. A group of computationally derived features (e.g., metal NBO charges, steric descriptors, torsion angles) were acquired for a library of pyridine-oxazoline ligands. Correlation studies were employed to examine steric/electronic features described by each descriptor, followed by application of the said descriptors in modeling the results of two reaction types, the site-selective redox-relay Heck reaction and the enantioselective Carroll rearrangement, affording simple, well-validated models. Through exptl. validation and extrapolation, parameters derived from ground state metal complexes were found to be advantageous over those from the free ligand.

ACS Catalysis published new progress about Bond angle, torsional. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hilton, Margaret J’s team published research in Journal of Organic Chemistry in 2014-12-19 | 1416819-91-4

Journal of Organic Chemistry published new progress about Cyclization. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Formula: C13H15F3N2O.

Hilton, Margaret J.; Xu, Li-Ping; Norrby, Per-Ola; Wu, Yun-Dong; Wiest, Olaf; Sigman, Matthew S. published the artcile< Investigating the Nature of Palladium Chain-Walking in the Enantioselective Redox-Relay Heck Reaction of Alkenyl Alcohols>, Formula: C13H15F3N2O, the main research area is alkene palladium catalysis redox relay Heck arylation alkenylalc M06.

The mechanism of the redox-relay Heck reaction was investigated using deuterium-labeled substrates. Results support a pathway through a low energy palladium-alkyl intermediate that immediately precedes product formation, ruling out a tautomerization mechanism. DFT calculations of the relevant transition structures at the M06/LAN2DZ+f/6-31+G* level of theory show that the former pathway is favored by 5.8 kcal/mol. Palladium chain-walking toward the alc., following successive β-hydride eliminations and migratory insertions, is also supported in this study. The stereochem. of deuterium labels is determined, lending support that the catalyst remains bound to the substrate during the relay process and that both cis- and trans-alkenes form from β-hydride elimination.

Journal of Organic Chemistry published new progress about Cyclization. 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Marrazzo, John-Paul R’s team published research in Journal of Organic Chemistry in 2022-01-07 | 1416819-91-4

Journal of Organic Chemistry published new progress about 1,3-Dicarbonyl compounds 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, Related Products of 1416819-91-4.

Marrazzo, John-Paul R.; Chao, Allen; Li, Yajun; Fleming, Fraser F. published the artcile< Copper-Catalyzed Conjugate Additions to Isocyanoalkenes>, Related Products of 1416819-91-4, the main research area is isocyanoalkane preparation; isocyanoalkene nucleophile conjugate addition reaction catalyst copper.

A copper iodide-Pyox complex catalyzed the first conjugate addition of diverse sulfur, nitrogen, and carbon nucleophiles to isocyanoalkenes to gave isocyano(aryl)ethyl(sulfane/alkyl/imidazole/isoindoline-1,3-dione) I [Ar = 2-MeOC6H4, 4-PhC6H4, R = allylsulfanyl, imidazol-1-yl, cyano(diphenyl)methyl, etc.]. The anionic addition generates metalated isocyanoalkanes capable of SNi displacements, provided a rapid route to a series of functionalized, cyclic isocyanoalkanes II [R1 = 2-MeC6H4, 2-MeOC6H4, 4-PhC6H4, etc.; R2 = H, n-Pr, R3 = Me, Et, t-Bu] and III. The Cu(I)I-Pyox complex efficiently catalyzes a first-in-class conjugate addition affording a range of complex, functionalized isocyanoalkanes I, II and III that were otherwise challenging to synthesize while laying a foundation for catalytic reactions that maintain the isocyanide group.

Journal of Organic Chemistry published new progress about 1,3-Dicarbonyl compounds 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, Related Products of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Chun’s team published research in Chemical Science in 2017 | 1428537-19-2

Chemical Science published new progress about Alkenals Role: SPN (Synthetic Preparation), PREP (Preparation). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Safety of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Zhang, Chun; Tutkowski, Brandon; DeLuca, Ryan J.; Joyce, Leo A.; Wiest, Olaf; Sigman, Matthew S. published the artcile< Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters>, Safety of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is alkenyl aldehyde ketone preparation enantioselective diastereoselective; allylic alkenol alkenyl triflate redox relay Heck palladium catalyst.

An enantioselective, redox-relay Heck alkenylation of trisubstituted allylic alkenol substrates with alkenyl triflates was developed to afford alkenyl aldehydes/ketones e.g., I. This process enabled the construction of vicinal stereocenters in high diastereo- and enantioselectivity and allowed the formation of enolizable α-carbonyl methyl-substituted stereocenters with no observed epimerization under the reported reaction conditions.

Chemical Science published new progress about Alkenals Role: SPN (Synthetic Preparation), PREP (Preparation). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Safety of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Allen, Jamie R’s team published research in Journal of the American Chemical Society in 2019-06-05 | 1416819-91-4

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

Allen, Jamie R.; Bahamonde, Ana; Furukawa, Yukino; Sigman, Matthew S. published the artcile< Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction>, SDS of cas: 1416819-91-4, the main research area is indolylalkanal chemoselective enantioselective preparation; chemoselective enantioselective aza Wacker reaction allylic homoallylic alc indole; enantioselective alkylation indole allylic homoallylic alc palladium catalyst; stereochem mechanism aza Wacker reaction deuterated allylic alc indole.

In the presence of Pd(MeCN)2(OTs)2 and a nonracemic pyridinyloxazoline, 3-substituted indoles such as 3-phenylindole underwent intermol., chemoselective, and enantioselective alkylation/aza-Wacker reactions with cis-allylic and cis-homoallylic alcs. such as (Z)-EtCH:CHCH2OH mediated by p-benzoquinone in 1,2-dichloroethane to yield nonracemic β- and γ-(1-indolyl)alkanals such as I; enamines generated under other conditions were not formed. The mechanism was studied using the reaction of a deuterium-labeled allylic alc.; the stereochem. of the product supported a syn amino-palladation mechanism for the reaction.

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

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Herrera, Christian Leonardo’s team published research in Advanced Synthesis & Catalysis in 2022-06-07 | 1416819-91-4

Advanced Synthesis & Catalysis 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, Computed Properties of 1416819-91-4.

Herrera, Christian Leonardo; Santiago, Joao Victor; Pastre, Julio Cezar; Correia, Carlos Roque Duarte published the artcile< In Tandem Auto-Sustainable Enantioselective Heck-Matsuda Reactions Directly from Anilines>, Computed Properties of 1416819-91-4, the main research area is aniline cyclopentenol palladium catalyst enantioselective Heck Matsuda reaction green; phenyl cyclopentenol preparation; cyclopentenedicarboxylate aniline palladium catalyst enantioselective Heck Matsuda reaction green; dimethyl phenyl cyclopentenedicarboxylate preparation; butenediol aniline palladium catalyst enantioselective Heck Matsuda reaction green; aryl furanone preparation.

An in tandem enantioselective Heck-Matsuda (HM) reaction of cyclic and acyclic olefins directly from anilines was described. The method relied on a process involving the progressive in situ diazotization of the starting anilines followed by a palladium-catalyzed Heck-Matsuda arylation using chiral N,N-ligands. This intermol. enantioselective HM arylation strategy was applied to the desymmetrization of three distinct unactivated olefins as proof of concept. The method demonstrates broad substrate scope furnishing the Heck adducts in good to excellent enantiomeric ratios of up to 99:1, high diastereoselectivities (cyclopenten-3-ol with>20:1 dr), and good overall yields of up to 82% over 2 or 3 steps.

Advanced Synthesis & Catalysis 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, Computed Properties of 1416819-91-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem