Palladium-Catalyzed E-Selective Oxidative Amination of Aromatic Amine with 3-Butenoic Acid

Article Chemistry, Organic

Enamines and their variants as intermediates for synthesis of aza-heterocycles with applications in MCRs

D. Magoo et al.

Summary: A diverse library of nitrogen containing heterocyclic compounds can be synthesized through the versatility of enamine intermediates and multicomponent reactions.

TETRAHEDRON (2022)

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Article Chemistry, Multidisciplinary

Amine-catalyzed synthesis of N2-sulfonyl 1,2,3-triazole in water and the tunable N2-H 1,2,3-triazole synthesis in DMSO via metal-free enamine annulation

Yanhui Guo et al.

Summary: Selective synthesis of N-2-sulfonyl and N-2-H1,2,3-triazoles was achieved through organocatalytic annulation of enaminone/enaminoester with sulfonyl azide. The unconventional selectivity for N-2-sulfonyl 1,2,3-triazoles occurred in pure water, where the hydrogen bond effect between water and the intermediate formed by enamine-azide corporation accounted for the novel reaction selectivity. In contrast, the reactions conducted in DMSO specifically yielded N-2-H 1,2,3-triazoles in the absence of such hydrogen bond effect.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Reaction of α-Diazopyrroles with Enamines: Synthesis of Pyrrolo[2,1-c][1,2,4]triazines and α-(1,2,5-Triazapenta-1,3-dienyl)pyrroles

Nikita A. Kaminskiy et al.

Summary: This study discovered that alpha-diazopyrroles selectively react with enamines at room temperature to produce organic compounds, which can be used for the synthesis of functionalized heterocycles.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

A Bi(OTf)3-Promoted Hydrosulfonylation of Alkenes with Sulfonyl Hydrazides: An Approach to Branched Sulfones

Zheng Zhou et al.

Summary: The Bi(OTf)(3)-promoted hydrosulfonylation of alkenes with sulfonyl hydrazides to produce branched sulfones is reported. Various branched sulfones were synthesized in moderate to good yields, highlighting the potential application of this reaction.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Deyun Qian et al.

Summary: A nickel-catalyzed hydroalkylation method has been developed to assemble a wide range of chiral alkyl amines with high regio- and enantioselectivity from enecarbamates and alkyl halides. The method is suitable for both nonactivated and activated alkyl halides, producing enantiomerically enriched amines with high functional group tolerance.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Palladium-Catalyzed Direct C-H Arylation of 3-Butenoic Acid Derivatives

Shan Yang et al.

Summary: This study demonstrates a direct method for synthesizing 4-aryl-3-butenoic acid, with the potential bioactivity of the derivatives being highlighted based on the previously reported bioactivity of 4-phenyl-3-butenoic acid.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclization of Alkenyl Phosphoramidates

Anand H. Shinde et al.

Summary: Highly diastereoselective tethered aza-Wacker cyclization reactions of alkenyl phosphoramidates were achieved by arming the phosphoramidate tether with 5-chloro-8-quinolinol, leading to >20:1 diastereoselectivity. The substrate scope with respect to alkenyl alcohols and phosphoramidate tether was extensively explored. The product cyclophosphoramidates were demonstrated to be valuable synthons, including for tether removal.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Copper-Catalyzed Diamination of Unactivated Alkenes With Electron-Rich Amino Sources

Yang Li et al.

Summary: Using a directing-group strategy, a copper-catalyzed diamination of unactivated alkenes efficiently generates symmetrical diamines with high diastereoselectivity using readily available dialkylamines as amino sources, while unsymmetrical diamines require a one-pot or two-step operation. These reactions are proposed to proceed through aziridinium intermediates.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Mateusz Garbacz et al.

Summary: This study presents a new method for the synthesis of allylamines through cross-coupling of alkyl bromides with 3-bromoallylamines, using a combination of photoredox and Ni catalysis. The reaction is performed under mild conditions, with blue light irradiation and a specific organic dye as a photocatalyst, enabling the construction of complex multifunctional allylamine derivatives.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Organic

Metal-Free Synthesis of 1,2,3-Triazoles in Pure Water via the Enamine Modified Annulation Reactions with Tosyl Azide

Xixi Zheng et al.

Summary: The study achieved the synthesis of full substituted 1,2,3-triazoles and N-alkyl sulfonamides with high efficiency using Et3N catalysis, with water as the sole reaction medium. The key factor enabling the water mediated synthesis was found to be the use of stable NH-enamines as substrates.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Palladium/Copper-Mediated Switchable Approaches towards (Chloro)ethenylphosphorylamides by Phosphorylamides and Alkenes

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Directing-Group-Based Strategy Enabling Intermolecular Heck-Type Reaction of Cycloketone Oxime Esters and Unactivated Alkenes

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ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

Salient features of theaza-Wacker cyclization reaction

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MOLECULES (2019)

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

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Daniel G. Kohler et al.

NATURE CHEMISTRY (2018)

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Review Chemistry, Organic

Catalytic asymmetric enamine protonation reaction

Niankai Fu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Palladium(ii)-catalyzed -selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids

Rei Matsuura et al.

CHEMICAL SCIENCE (2018)

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Article Chemistry, Organic

Synthesis of 2H-Azirines via Iodine-Mediated Oxidative Cyclization of Enamines

Manman Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Regioselective Metal-Free Aza-Heck Reactions of Terminal Alkenes Catalyzed by Phosphine Selenides

Tianyi Zheng et al.

ORGANIC LETTERS (2018)

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Review Chemistry, Physical

Oxidoreductase-Catalyzed Synthesis of Chiral Amines

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ACS CATALYSIS (2018)

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AMERICAN JOURNAL OF KIDNEY DISEASES (2017)

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Article Chemistry, Organic

Systematic Investigation into the Matsuda-Heck Reaction of α-Methylene Lactones: How Conformational Constraints Direct the β-H-Elimination Step

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β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation

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Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

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Dehydrogenative Allylic Aminations of But-3-enoic Acid Derivatives

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SYNTHESIS-STUTTGART (2016)

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Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions

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Misuse and Abuse of Pregabalin and Gabapentin: Cause for Concern?

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Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

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Palladium-Catalyzed Oxidative Coupling of Aromatic Primary Amines and Alkenes under Molecular Oxygen: Stereoselective Assembly of (Z)-Enamines

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Terahertz pulse spectroscopy of biological materials: L-glutamic acid

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Palladium-Catalyzed E-Selective Oxidative Amination of Aromatic Amine with 3-Butenoic Acid

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