Tag: M.W=250-300

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

Guo, Zi-Qiong; Xu, Hui; Wang, Xing; Wang, Zhen-Yu; Ma, Biao; Dai, Hui-Xiong published the artcile< C3-Arylation of indoles with aryl ketones via C-C/C-H activations>, Application In Synthesis of 1428537-19-2, the main research area is arylindole preparation regioselective; indole aryl ketone arylation palladium catalyst carbon hydrogen activation.

C3-Arylation of indoles with aryl ketones is accomplished via palladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.

Chemical Communications (Cambridge, United Kingdom) published new progress about Aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application In Synthesis of 1428537-19-2.

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

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

Khan, Ismat Ullah; Kattela, Shivashankar; Hassan, Abbas; Correia, Carlos Roque Duarte published the artcile< Enantioselective total synthesis of the highly selective sphingosine-1-receptor VPC01091 by the Heck desymmetrization of a non-activated cyclopentene-fused spiro-pyrrolidinone>, Application of C13H15F3N2O, the main research area is stereoselective Heck Matsuda desymmetrization cyclopentene fused spiropyrrolidinone arenediazonium tetrafluoroborate; enantioselective total synthesis VPC01091.

A novel, efficient and enantioselective Heck-Matsuda desymmetrization of non-activated cyclopentene-fused spiro-pyrrolidinones was developed. The reaction provided the Heck products in good to excellent yields and selectivities and tolerated a variety of functional groups in arenediazonium tetrafluoroborates (12 examples) with respect to its electronics and substitution patterns. This methodol. was successfully applied in the concise enantioselective total synthesis of VPC01091 (I), a drug candidate for the treatment of multiple sclerosis.

Organic & Biomolecular Chemistry published new progress about Desymmetrization. 1428537-19-2 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Application of C13H15F3N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem