Month: October 2022

Liu, Richard Y.; Bae, Minwoo; Buchwald, Stephen L. published the artcile< Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes>, Name: tert-Butyl 3-cyanopiperidine-1-carboxylate, the main research area is copper catalyst dehydration primary amide hydrosilane; nitrile preparation.

Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. A copper-hydride(CuH)-catalyzed process is reported that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups and can be performed using a simple ligand, inexpensive siloxanes and low catalyst loading.

Journal of the American Chemical Societypublished new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Name: tert-Butyl 3-cyanopiperidine-1-carboxylate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Nakajima, Noriyuki; Ubukata, Makoto published the artcile< Preparation of nitriles from primary amides under Swern oxidation conditions>, Synthetic Route of 91419-53-3, the main research area is Swern oxidation carboxamide; nitrile preparation.

In order to establish a mild conversion method of primary amides to nitriles, various types of carboxamides were treated under Swern oxidation conditions, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain desired nitriles in 75-96% yields.

Tetrahedron Letterspublished new progress about Amides Role: RCT (Reactant), RACT (Reactant or Reagent). 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Synthetic Route of 91419-53-3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wagener, Tobias; Lueckemeier, Lukas; Daniliuc, Constantin G.; Glorius, Frank published the artcile< Interrupted pyridine hydrogenation: Asymmetric synthesis of δ-lactams>, SDS of cas: 25504-47-6, the main research area is delta lactam preparation oxazolidinone substituted pyridine interrupted hydrogenation; asymmetric catalysis; heterogeneous catalysis; hydrogenation; lactams; nitrogen heterocycles.

Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C-H and N-H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chem. complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work the authors report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.

Angewandte Chemie, International Editionpublished new progress about Hydrogenation. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, SDS of cas: 25504-47-6.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Gross, Kathleen M. Bertini; Beak, Peter published the artcile< Complex-Induced Proximity Effects: The Effect of Varying Directing-Group Orientation on Carbamate-Directed Lithiation Reactions>, SDS of cas: 149518-50-3, the main research area is proximity effect complex induced; carbamate directed lithiation.

A series of selected bicyclic carbamates in which the range of accessible angles and distances between the carbonyl group and the proton removed in an α-lithiation reaction are structurally defined have been investigated. Oxazolidinones I (n = 1, 2; R = i-Pr, t-Bu) undergo stereoselective lithiation-substitution reactions to provide cis-II as the major diastereomers. Two series of competition experiments show that the conformationally restricted carbamates undergo lithiation via complexes more efficiently than Boc amines (e.g., N-Boc-pyrrolidine, N-Boc-piperidine). These results along with semiempirical calculations suggest that a small dihedral angle and a calculated distance of 2.78 Å between the carbamate carbonyl oxygen and the proton to be removed are favorable for a carbamate-directed lithiation. A series of tin-lithium exchange experiments indicate that the configurational stability of a carbamate-stabilized organolithium species may be enhanced by restrictive geometry.

Journal of the American Chemical Societypublished new progress about Chelation (and configurational stability of carbanion intermediate). 149518-50-3 belongs to class piperidines, and the molecular formula is C12H21NO4, SDS of cas: 149518-50-3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Amani, Javad; Molander, Gary A. published the artcile< Direct Conversion of Carboxylic Acids to Alkyl Ketones>, Quality Control of 180181-05-9, the main research area is ketone preparation photoredox synergistic catalytic coupling carboxylic acid alkyltrifluoroborate; synergistic photoredox nickel catalytic coupling carboxylic acid alkyltrifluoroborate.

An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carboxylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.

Organic Letterspublished new progress about Carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (activated). 180181-05-9 belongs to class piperidines, and the molecular formula is C22H23NO4, Quality Control of 180181-05-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Badir, Shorouk O.; Lipp, Alexander; Krumb, Matthias; Cabrera-Afonso, Maria Jesus; Kammer, Lisa Marie; Wu, Victoria E.; Huang, Minxue; Csakai, Adam; Marcaurelle, Lisa A.; Molander, Gary A. published the artcile< Photoredox-mediated hydroalkylation and hydroarylation of functionalized olefins for DNA-encoded library synthesis>, Synthetic Route of 180181-05-9, the main research area is phthalimide ester DNA conjugated trifluoromethyl alkene photoredox catalyst trifluoromethylation; DNA encoded trifluoromethylalkyl aryl amide preparation; alkene DNA conjugated aryl iodide photoredox catalyst reductive alkylation; alkylaryl DNA encoded amide preparation.

DNA-encoded library (DEL) technol. features a time- and cost-effective interrogation format for the discovery of therapeutic candidates in the pharmaceutical industry. To develop DEL platforms, the implementation of water-compatible transformations that facilitate the incorporation of multifunctional building blocks (BBs) with high C(sp3) carbon counts is integral for success. In this report, a decarboxylative-based hydroalkylation of DNA-conjugated trifluoromethyl-substituted alkenes enabled by single-electron transfer (SET) and subsequent hydrogen atom termination through electron donor-acceptor (EDA) complex activation was detailed. In a further photoredox-catalyzed hydroarylation protocol, the coupling of functionalized, electronically unbiased olefins was achieved under air and within minutes of blue light irradiation through the intermediacy of reactive (hetero)aryl radical species with full retention of the DNA tag integrity. Notably, these processes operate under mild reaction conditions, furnishing complex structural scaffolds with a high d. of pendant functional groups.

Chemical Sciencepublished new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 180181-05-9 belongs to class piperidines, and the molecular formula is C22H23NO4, Synthetic Route of 180181-05-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem