Category: 1416819-91-4

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; 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.; 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.; 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

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; 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

Liu, Jianbo; Yuan, Qianjia; Toste, F. Dean; Sigman, Matthew S. published the artcile< Enantioselective construction of remote tertiary carbon-fluorine bonds>, Formula: C13H15F3N2O, the main research area is tertiary benzylic fluoroalkane enantioselective synthesis; enantioselective Heck coupling acyclic alkenyl fluoride arylboronic acid.

The carbon-fluorine bond engenders distinctive physicochem. properties and significant changes to general reactivity. The development of catalytic, enantioselective methods to set stereocenters that contain a benzylic C-F bond is a rapidly evolving goal in synthetic chem. Although there have been notable advances that enable the construction of secondary stereocenters that contain both a C-F and a C-H bond on the same carbon, significantly fewer strategies are defined to access stereocenters that incorporate a tertiary C-F bond, especially those remote from pre-existing activating groups. Here we report a general method that establishes C-F tertiary benzylic stereocenters by forging a C-C bond via a Pd-catalyzed enantioselective Heck reaction of acyclic alkenyl fluorides with arylboronic acids. This method provides a platform to rapidly incorporate significant functionality about the benzylic tertiary fluoride by virtue of the diversity of both reaction partners, as well as the ability to install the stereocenters remotely from pre-existing functional groups.

Nature Chemistry published new progress about Allylic alcohols 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, Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Penglin; Zhang, Min; Ji, Yuqi; Xing, Mimi; Zhao, Qian; Zhang, Chun published the artcile< Nickel-Catalyzed Highly Selective Hydroalkenylation of Alkenyl Boronic Esters to Access Allyl Boron>, Application of C13H15F3N2O, the main research area is nickel catalyzed hydroalkenylation alkenyl boronic ester cyclohexenyl triflate; boronate allyl preparation oxidation; allyl alc preparation.

Allyl B derivatives are valuable building blocks in the synthesis of natural products and bioactive mols. Herein, a practical strategy of Ni-catalyzed highly selective hydroalkenylation of alkenyl boronic esters was developed. Under the mild reaction conditions, a variety of allyl boronic esters were accessed with excellent chemo- and regioselectivity. The mechanism of this transformation was illustrated by control experiments and kinetic studies.

Organic Letters published new progress about Alkenylation catalysts (Ni complexes). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application of C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hickey, David P.; Sandford, Christopher; Rhodes, Zayn; Gensch, Tobias; Fries, Lydia R.; Sigman, Matthew S.; Minteer, Shelley D. published the artcile< Investigating the Role of Ligand Electronics on Stabilizing Electrocatalytically Relevant Low-Valent Co(I) Intermediates>, Safety of (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is bidentate ligand electronics cobalt complex electrochem low valence intermediate.

Cobalt complexes have shown great promise as electrocatalysts in applications ranging from hydrogen evolution to C-H functionalization. However, the use of such complexes often requires polydentate, bulky ligands to stabilize the catalytically active Co(I) oxidation state from deleterious disproportionation reactions to enable the desired reactivity. Herein, we describe the use of bidentate electronically asym. ligands as an alternative approach to stabilizing transient Co(I) species. Using disproportionation rates of electrochem. generated Co(I) complexes as a model for stability, we measured the relative stability of complexes prepared with a series of N,N-bidentate ligands. While the stability of Co(I)Cl complexes demonstrates a correlation with exptl. measured thermodn. properties, consistent with an outer-sphere electron transfer process, the set of ligated Co(I)Br complexes evaluated was found to be preferentially stabilized by electronically asym. ligands, demonstrating an alternative disproportionation mechanism. These results allow a greater understanding of the fundamental processes involved in the disproportionation of organometallic complexes and have allowed the identification of cobalt complexes that show promise for the development of novel electrocatalytic reactions.

Journal of the American Chemical Society published new progress about Activation energy. 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

Sun, Manman; Wu, Haijian; Xia, Xiangyu; Chen, Weida; Wang, Zhiming; Yang, Jianguo published the artcile< Asymmetric Palladium-Catalyzed C-H Functionalization Cascade for Synthesis of Chiral 3,4-Dihydroisoquinolones>, Formula: C13H15F3N2O, the main research area is sulfonylbenzamide diene palladium bond activation enantioselective allylation cascade green; dihydroisoquinolone stereoselective preparation.

A palladium-catalyzed C-H functionalization/intramol. asym. allylation cascade of N-sulfonyl benzamides with 1,3-dienes has been developed. In the presence of a chiral pyridine-oxazoline ligand, this protocol enables the synthesis of chiral 3,4-dihydroisoquinolones, e.g., I, in yields of up to 83% with enantioselectivities of up to 96%, using environmentally friendly air as the terminal oxidant.

Journal of Organic Chemistry published new progress about 1,3-Alkadienes Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Formula: C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem