4.7 Article

Discovering and Evaluating the Reducing Abilities of Polar Alkanes and Related Family Members as Organic Reductants Using Thermodynamics

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

Water-Assisted and Catalyst-Free Hetero-Michael Additions: Mechanistic Insights from DFT Investigations

Hui Yang et al.

Summary: The study investigates the reaction mechanisms of six catalyst-free hetero-Michael addition reactions in water using DFT calculations. Water molecules are directly involved in the transition states, playing a catalytic role in lowering the activation barrier, especially for thia-Michael reactions. The calculated low reaction barriers are in good agreement with the observed facile reactions, indicating the important role of water in these processes.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Chemistry, Multidisciplinary

Enantioselective Organocatalytic Michael Addition Reactions Catalyzed by Proline/Prolinol/Supported Proline based Organocatalysts: An Overview

Sai Deepak Pasuparthy et al.

Summary: Enantioselective organocatalytic Michael addition reactions have emerged as a significant pathway for synthesizing a variety of stereochemical products under mild conditions.

CHEMISTRYSELECT (2022)

Article Multidisciplinary Sciences

Doubly stereoconvergent crystallization enabled by asymmetric catalysis

Pedro de Jesus Cruz et al.

Summary: This study reports the discovery and development of a new synthetic method that allows simultaneous control over multiple stereogenic centers for efficient preparation of pharmaceutical compounds. By merging asymmetric Michael addition and crystallization-induced diastereomer transformation, useful compounds with three contiguous stereogenic centers have been successfully synthesized.

SCIENCE (2022)

Article Chemistry, Applied

Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer

Natalia A. Larionova et al.

Summary: Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes enables efficient formal hydrogenation under mild conditions, with good functional group compatibility. The reaction is not affected by substituents and is supported by HAT-driven mechanism.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Review Chemistry, Physical

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Sushanta Kumar Parida et al.

Summary: NHPI esters and their derivatives have emerged as a forefront in synthetic methods, undergoing reductive fragmentation to generate radicals for diverse synthetic transformations. They are widely applicable in cascade annulations as well as medicinal chemistry and natural product synthesis. This review categorizes the progress in this field according to bond formation nature, providing representative examples with mechanistic details and highlighting challenges and future directions.

ACS CATALYSIS (2021)

Article Chemistry, Physical

Modular Enantioselective Synthesis of cis-Cyclopropanes through Self-Sensitized Stereoselective Photodecarboxylation with Benzothiazolines

Matteo Costantini et al.

Summary: A modular approach from olefin materials to the synthesis of chiral cis-cyclopropanes is enabled by the discovery of the electron donor-acceptor interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, with benzothiazoline reagent serving as a photoreductant, stereoselective hydrogen-atom donor, and a Bronsted acid. This study introduces benzothiazolines as accessible and easily tunable self-sensitized photoreductants, expanding their potential applications beyond enantioselective synthesis of cis-cyclopropanes.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Accessing Photoredox Transformations with an Iron(III) Photosensitizer and Green Light

Akin Aydogan et al.

Summary: Efficient excited-state electron transfer was achieved between an iron(III) photosensitizer and organic electron donors under green light irradiation, using a long-lived and luminescent ligand-to-metal charge-transfer (LMCT) excited state iron photosensitizer. The catalyst demonstrated yields exceeding 90% in a benchmark dehalogenation reaction, with enhanced stability compared to a typical photosensitizer. The initial catalytic step involved electron transfer from an amine to the photoexcited iron sensitizer, shown to occur with a large cage-escape yield, indicating potential advantages of Fe(III) photosensitizers in reductive electron transfer.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids

Jose A. C. Delgado et al.

Summary: This technology utilizes alkyl radicals to selectively alkylate dehydroalanine, offering a convenient method for the synthesis of unnatural amino acids and late-stage functionalization of pharmaceuticals.

ORGANIC LETTERS (2021)

Article Chemistry, Inorganic & Nuclear

Lewis Acidic Telluronium Cations: Enhanced Chalcogen-Bond Donor Properties and Application to Transfer Hydrogenation Catalysis

Benyu Zhou et al.

Summary: This study describes the synthesis and structures of two new bifunctional tellurides and investigates their methylation reactions and catalytic activities. One mixed-valent telluride/telluronium cation showed catalytic activity in hydrogenation reaction, while simple telluronium cations did not exhibit this activity.

ORGANOMETALLICS (2021)

Article Chemistry, Multidisciplinary

Quantitative Estimation of the Hydrogen-Atom-Donating Ability of 4-Substituted Hantzsch Ester Radical Cations

Guang-Bin Shen et al.

Summary: This study investigated the thermodynamic and kinetic properties of 4-substituted Hantzsch ester radical cations in terms of hydrogen-atom-donating ability, comparing them with other antioxidants. The results showed that the R substituents in the 4-position significantly impact the antioxidant properties of the radical cations.

ACS OMEGA (2021)

Article Chemistry, Multidisciplinary

Holistic Prediction of the pKa in Diverse Solvents Based on a Machine-Learning Approach

Qi Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

Synthesis of Amino Acids by Base-Enhanced Photoredox Decarboxylative Alkylation of Aldimines

Jiancheng Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

A Redox-Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions

Thomas van Leeuwen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Agriculture, Multidisciplinary

Critical Re-Evaluation of DPPH assay: Presence of Pigments Affects the Results

JuDong Yeo et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Thermodynamic Hydricities of Biomimetic Organic Hydride Donors

Stefan Ilic et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Organic

Nitrile-assisted oxidation over oxidative-annulation: Pd-catalyzed α,β-dehydrogenation of α-cinnamyl β-keto nitriles

Rajender Nallagonda et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

Review Chemistry, Multidisciplinary

Benzothiazoline: Versatile Hydrogen Donor for Organocatalytic Transfer Hydrogenation

Chen Zhu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Review Agriculture, Multidisciplinary

Use and Abuse of the DPPH• Radical

Mario C. Foti

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Mechanism of Hydride Transfer Reaction from β-Substituted Carbanions to a Carbocation

Fengrui Liu et al.

CHEMISTRY LETTERS (2014)

Article Chemistry, Organic

Unusual Reaction Constant for Hydride Transfer from a Carbanion to 9-Arylxanthyliums

Fengrui Liu et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Review Chemistry, Multidisciplinary

Transfer hydrogenation with Hantzsch esters and related organic hydride donors

Chao Zheng et al.

CHEMICAL SOCIETY REVIEWS (2012)

Article Chemistry, Organic

A Thermodynamic and Kinetic Study of Hydride Transfer of a Caffeine Derivative

Xiaozhen Han et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Chemistry, Organic

Study on comparison of reducing ability of three organic hydride compounds

Yi-Si Feng et al.

TETRAHEDRON (2012)

Article Chemistry, Organic

Determination of Hydride Affinities of Various Aldehydes and Ketones in Acetonitrile

Xiao-Qing Zhu et al.

ORGANIC LETTERS (2011)

Review Chemistry, Multidisciplinary

Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications

Jeffrey J. Warren et al.

CHEMICAL REVIEWS (2010)

Review Chemistry, Multidisciplinary

Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters

Stephane G. Ouellet et al.

ACCOUNTS OF CHEMICAL RESEARCH (2007)

Article Chemistry, Organic

Towards organo-click reactions: development of pharmaceutical ingredients by using direct organocatalytic bio-mimetic reductions

Dhevalapally B. Ramachary et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2006)

Article Chemistry, Multidisciplinary

A facile experimental method to determine the hydride affinity of polarized olefins in acetonitrile

XQ Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)