Category: 1416819-91-4

Dai, Qiang; Li, Wenbo; Li, Zhiming; Zhang, Junliang published the artcile< P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides>, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is phosphine chiral palladium catalyzed arylation phosphine oxide aryl bromide; chiral aryldiphosphine oxide preparation crystal structure; mol structure chiral aryl diphosphine oxide palladium sulfinamidephosphine; palladium sulfinamidephosphine chiral complex preparation crystal structure.

The development of transition-metal-catalyzed methods for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Herein, the authors present a direct Pd/Xiao-Phos-catalyzed cross-coupling reaction of easily accessible secondary phosphine oxides and aryl bromides, which provides rapid access to P-chiral phosphine oxides. The reaction proceeds efficiently with a wide array of reaction partners to deliver various tertiary phosphine oxides in up to 96% yield and 97% ee. Also, the synthesis of DiPAMP ligand and its analogs was also realized, which demonstrates a suitable pathway to switching the branched chain of DiPAMP.

Journal of the American Chemical Society published new progress about Aryl bromides 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

Werner, Erik W.; Mei, Tian-Sheng; Burckle, Alexander J.; Sigman, Matthew S. published the artcile< Enantioselective Heck Arylations of Acyclic Alkenyl Alcohols Using a Redox-Relay Strategy>, Name: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is beta gamma delta aryl ketone aldehyde enantioselective regioselective preparation; allylic homoallylic alc enantioselective Heck reaction aryldiazonium salt; palladium pyridinyloxazolidine catalyst enantioselective Heck reaction aryldiazonium salt alkenol; stereospecificity Heck reaction aryldiazonium salt alkenol olefin geometry; safety aryldiazonium salt potential explosive.

Nonracemic β-, γ-, and δ-aryl ketones such as (S)-4-MeO2CC6H4CHMeCH2COMe were prepared in 52-85% yields, 90:10-99:1 er, and with high regioselectivities by Heck reactions of phenyldiazonium tetrafluoroborate or aryldiazonium hexafluorophosphates (generated from the corresponding arylamines) with acyclic allylic, homoallylic, or bishomoallylic alcs. such as (E)-MeCH(OH)CH:CHMe in the presence of tris(dibenzylideneacetone)dipalladium [Pd2(dba)3] and the nonracemic trifluoropyridinyl oxazolidine I. I and Pd2(dba)3 imparted notable regioselectivity during migratory insertion and promoted migration of alkene unsaturation toward the alc. to form ketones or aldehydes. (E)- and (Z)-allylic and homoallylic alcs. underwent stereospecific Heck reactions to give enantiomeric products; the alc. stereochem. in the racemic unsaturated alcs. did not affect the enantioselectivities of their reactions. The aryldiazonium salts used as reactant can be explosive and should be handled with caution.

Science (Washington, DC, United States) published new progress about Alcohols, unsaturated 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, Name: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 (S)-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). 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

Mei, Tian-Sheng; Werner, Erik W.; Burckle, Alexander J.; Sigman, Matthew S. published the artcile< Enantioselective Redox-Relay Oxidative Heck Arylations of Acyclic Alkenyl Alcohols using Boronic Acids>, SDS of cas: 1416819-91-4, the main research area is acyclic alkenol arylboronic acid enantioselective regioselective oxidative Heck arylation; aryl aldehyde stereoselective preparation; ketone aryl stereoselective preparation.

A general, highly selective asym. redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alc.

Journal of the American Chemical Society published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation) (aralkyl). 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

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