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Article
Chemistry, Organic
Andrea Brunetti et al.
Summary: This study presents the electrochemical carboxylation of Morita-Baylis-Hillman (MBH) acetates with CO2. The reaction occurs without the need for transition-metal catalysts and involves the cathodic reduction of MBH acetates to generate nucleophilic anions capable of trapping low-pressure CO2. Valuable succinate derivatives are obtained (20 examples) with high yields (up to 90%) and excellent functional group tolerance. The remarkable substrate-controlled (electronic nature) regioselectivity of the reaction is documented, and a mechanistic rationale is proposed based on control experiments.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Yu-Jiao Chen et al.
Summary: A novel Ketyl Mediated Polymerization (KMP) is developed by introducing ketyl radical anion species, which enables radical polymerization at the carbon radical site and anionic ring-opening polymerization at the oxygen anion site. Through KMP, organic synthesis and polymerization can be achieved simultaneously in one pot, resulting in the successful preparation of small molecules and polymers with low molecular weight distribution. This work expands the reaction mode and method libraries of organic chemistry and polymer chemistry, saving time, labor, resources, and energy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Prabhat Kumar Baroliya et al.
Summary: Electrochemically promoted transition metal-catalyzed C-H functionalization is a promising area of research, but it is still at an early stage compared to traditional chemical-based oxidizing agents. Recent reports have shown increased attention on electrochemically promoted metal-catalyzed C-H functionalization. From the perspective of sustainability and cost effectiveness, electrochemically promoted oxidation of a metal catalyst offers a mild, efficient, and atom-economical alternative to traditional chemical oxidants. This Review discusses advances in the field of transition metal-electrocatalyzed C-H functionalization and how electricity enables metal-catalyzed C-H functionalization in an economic and sustainable way.
Review
Chemistry, Organic
Cai Zhang et al.
Summary: This review article summarizes recent developments in electrochemical cascade cyclization reactions for the synthesis of carbon rings and heterocycles, including pyridines, quinolines, phenanthridines, cinnolines, 1,4-dihydroquinolines, oxindoles, imidazo[1,5-a]pyridines, imidazoles, etc. The works reported from 2012 to 2022 are divided into two major sections: heterocycle construction and carbocycle construction reactions.
SYNTHESIS-STUTTGART
(2023)
Review
Electrochemistry
Chad E. Hatch et al.
Summary: Electrochemical techniques have played a crucial role in the total synthesis of natural products since the pioneering work of Kolbe in the mid 1800s. These techniques have expanded over time, changing the way chemists approach and think about natural products. This review provides a perspective on the use of electrochemical techniques in enabling carbon-carbon bond formations in the assembly of important natural products, discussing mechanistic details and showcasing representative examples from the past few decades. These bond formations offer unique possibilities compared to conventional chemistries, allowing for complementary synthetic strategies.
Article
Multidisciplinary Sciences
Zhipeng Lin et al.
Summary: Electrochemistry, with the aid of data science and artificial intelligence, is increasingly being used for molecular synthesis. The authors have successfully utilized electrocatalyzed C-H activations for selective alkenylation in late-stage drug diversification. This approach eliminates the need for directing groups, which simplifies the synthesis process and reduces waste.
NATURE COMMUNICATIONS
(2023)
Review
Chemistry, Physical
Laurence Grimaud et al.
Summary: Although the concept of combining electrosynthesis with photochemistry has been around for many years, its practical application in organic synthesis has only recently emerged. This article highlights the power of this technology and how it can be used to overcome challenging oxidative or reductive processes. It presents recent chemical transformations that are otherwise inaccessible and discusses the important challenges and opportunities in this vibrant research field.
CURRENT OPINION IN ELECTROCHEMISTRY
(2023)
Review
Chemistry, Physical
Yanjun Li et al.
Summary: Organic electrochemistry is a sustainable method for achieving efficient and selective molecular transformations. This review focuses on recent advances in electro-organic synthesis and electrocatalysis for specialty chemicals, specifically highlighting progress made in the last two years until January 2023.
CURRENT OPINION IN ELECTROCHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Leonardo Rapisarda et al.
Summary: We present the chemo- and stereoselective electrochemical allylation/alkylation of ethers via C(sp(3))-H activation. This electrosynthetic protocol allows for the synthesis of a diverse library of functionalized ethers (35 examples) in high yields (up to 84%) through cathodic activation of a new type of redox-active carbonate (RAC), which triggers HAT (Hydrogen-Atom-Transfer) events by generating electrophilic oxy radicals. The process demonstrates high functional group tolerance and mild reaction conditions. Mechanistic elucidation through voltammetric analysis completes the study.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Simone Battaglioli et al.
Summary: This study demonstrates the dehydrogenative functionalization of styryl carbon-carbon double bonds with triflamide via dual visible-light photoredox/cobaloxime catalysis. A variety of allylic triflamides were synthesized in moderate to good yields under stoichiometric acceptorless conditions (up to 88%). Our dedicated labelling and spectroscopic experiments provided insights into the concatenated photo- and chemo-catalytic cycles.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Multidisciplinary
Philip L. Norcott
Summary: Selective deuteration of organic molecules through electrochemistry provides an effective alternative to traditional labelling strategies, offering milder reaction conditions and higher selectivity. Transition metal catalysis and photocatalysis have been successfully applied in this method, and electrochemistry is considered a potential approach as well.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Nicholas E. S. Tay et al.
Summary: Redox processes play a crucial role in synthetic methods involving electrochemistry and photoredox catalysis. Both approaches offer access to high energy intermediates that allow for unconventional bond formations. However, while they provide similar intermediates, electrochemistry and photoredox catalysis differ in their physical chemistry principles. Understanding these differences is essential for designing new transformations and bond disconnections.
Article
Chemistry, Multidisciplinary
Lorenzo Lombardi et al.
Summary: This methodology involves environmentally friendly covalent functionalization of reduced graphene oxide (rGO) nanosheets with arylazo sulfones through visible-light irradiation. It allows various tagged aryl units to be conveniently accommodated on the rGO surface, with mild reaction conditions, absence of photosensitizers, functional group tolerance, and high atomic fractions. Control experiments for mechanistic elucidation (Raman analysis) and chemical nanomanipulation of the tagged rGO surfaces were also conducted.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Lei Wang et al.
Summary: A sustainable, practical, and direct electrochemical pathway for the reduction of carbonyl compounds is presented, yielding alcohols or diols as major products with decent yields. The reaction takes place smoothly in the air at ambient temperatures with DABCO as the sacrificial reductant. Mechanistic studies reveal that direct electrochemical reduction followed by either protonation or radical-radical homocoupling is the main pathway.
Review
Chemistry, Multidisciplinary
Matthew C. Leech et al.
Summary: Organic electrosynthesis is an important discipline that utilizes electricity for redox reactions. This Review covers the fundamental aspects of the field, practical tips, and the basics of electroanalytical techniques.
NATURE REVIEWS CHEMISTRY
(2022)
Review
Chemistry, Physical
Skylar Blank et al.
Summary: Electrochemical cascades offer an elegant and sustainable pathway for organic synthesis, with the potential to significantly enhance reaction selectivity and efficiency.
CURRENT OPINION IN ELECTROCHEMISTRY
(2022)
Article
Chemistry, Organic
Giulio Bertuzzi et al.
Summary: This study demonstrates the effective and practical use of electrosynthesis for regio- and stereoselective alkylation of Morita-Baylis-Hillman compounds, resulting in high yields and wide functional group tolerance. It provides an efficient method for accessing densely functionalized cinnamate and oxindole derivatives.
Article
Chemistry, Multidisciplinary
Oleksandr Savateev et al.
Summary: Under photocatalytic conditions, Triethanolamine (TEOA) and N-tert-butyl diethanolamine undergo oxygenation with O-2, mediated by potassium poly(heptazine imide) (K-PHI) to form formyl esters of beta-hydroxyethylene formamides from the corresponding ethanolamines.
Article
Chemistry, Multidisciplinary
Lorenzo Lombardi et al.
Summary: This paper presents a nickel-catalyzed reductive cross-electrophile coupling reaction, which achieves high yields and high functional group tolerance in the arylation of trifluoroacetaldehyde through a solvent-assisted 1,2-Hydrogen Atom Transfer (HAT) process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Editorial Material
Chemistry, Organic
C. Oliver Kappe et al.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mohammad Rafiee et al.
Summary: Electrosynthesis involves transferring charge between two electrodes to promote chemical reactions. Controlling the current and potential can affect the reaction mechanism and product distribution. This Synopsis applies theoretical discussion to specific case studies to illustrate methods of adjusting and tracking electrical parameters for the optimization and monitoring of electroorganic reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yang Liu et al.
Summary: The study documents a visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids, leading to chemo- and regioselective allylic functionalization of styryl compounds, yielding allylic carboxylates. Both intermolecular and intramolecular variants are achieved in high yields, with a proposed mechanistic rationale based on experimental and spectroscopic investigation.
Review
Chemistry, Multidisciplinary
Luiz F. T. Novaes et al.
Summary: Electrochemistry has recently become a versatile strategy in achieving challenging transformations in synthetic organic chemistry. The use of redox-active electrocatalysts has increased in recent developments in electrosynthesis to enhance control over reactive intermediates. Electrocatalytic mediators allow for synthetic transformations to proceed in a manner different from purely chemical methods.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Carlo Bruno et al.
Summary: The presence of non-hexagonal rings in graphene leads to rippled graphene layers with valuable properties. An electrochemical method using corannulene polycondensation can produce egg-box shaped nanographene structures, demonstrating wavy graphene-like structures with conducting properties.
Review
Chemistry, Multidisciplinary
Cian Kingston et al.
ACCOUNTS OF CHEMICAL RESEARCH
(2020)
Article
Multidisciplinary Sciences
Yong Yuan et al.
NATURE COMMUNICATIONS
(2020)
Article
Multidisciplinary Sciences
Stefano Mazzanti et al.
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Jinjian Liu et al.
ACS CENTRAL SCIENCE
(2020)
Article
Chemistry, Organic
R. Daniel Little
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Review
Biochemistry & Molecular Biology
Rik H. Verschueren et al.
Article
Chemistry, Physical
Bogdan Kurpil et al.
Review
Chemistry, Multidisciplinary
Anton Wiebe et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Physical
Gregory K. Hodgson et al.
Article
Chemistry, Multidisciplinary
Qi-Liang Yang et al.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Organic
Lei Zhou et al.
Article
Chemistry, Physical
Zhong-Wei Hou et al.
Review
Chemistry, Multidisciplinary
Ming Yan et al.
Review
Chemistry, Multidisciplinary
Yann Pellegrin et al.
COMPTES RENDUS CHIMIE
(2017)
Article
Chemistry, Organic
Bichlien H. Nguyen et al.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Medicinal
Asa Rosenquist et al.
JOURNAL OF MEDICINAL CHEMISTRY
(2014)
Article
Chemistry, Organic
Guolei Zhao et al.
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
KK Kapoor et al.
TETRAHEDRON LETTERS
(2005)
Article
Chemistry, Organic
L Moisan et al.
TETRAHEDRON LETTERS
(2002)
Article
Chemistry, Organic
LH Zhou et al.
SYNTHETIC COMMUNICATIONS
(2000)
