Making electrochemistry easily accessible to the synthetic chemist

Green Chemistry, Год журнала: 2020, Номер 22(11), С. 3358 - 3375

Опубликована: Янв. 1, 2020

This tutorial bridges an important knowledge gap by providing easily accessible introduction that enables synthetic chemists to explore electrochemistry.

Язык: Английский

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Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(32), С. 13451 - 13457

Опубликована: Апрель 3, 2020

Abstract Asymmetric pallada‐electrocatalyzed C−H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective activations realized high position‐, diastereo‐, and enantio‐control under mild reaction conditions to obtain highly enantiomerically‐enriched biaryls fluorinated N−C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel BINOLs, dicarboxylic acids helicenes of value asymmetric catalysis. Mechanistic studies by experiments computation key insights into catalyst's mode action.

Язык: Английский

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Anodic Oxidation for the Stereoselective Synthesis of Heterocycles

Accounts of Chemical Research, Год журнала: 2019, Номер 53(1), С. 105 - 120

Опубликована: Дек. 24, 2019

ConspectusStereodefined aliphatic heterocycles are one of the fundamental structural motifs observed in natural products and biologically active compounds. Various strategies for synthesis these building blocks based on transition metal catalysis, organocatalysis, noncatalytic conditions have been developed. Although electrosynthesis has also utilized functionalization heterocycles, stereoselective transformations under electrochemical still a challenging field electroorganic chemistry.This Account consists four main topics related to our recent efforts diastereo- and/or enantioselective especially N-heterocycles, using anodic oxidations as key steps. The first topic is development synthetic methods multisubstituted piperidines pyrrolidines from anodically prepared α-methoxy cyclic amines. Our were primarily N-acyliminium ion chemistry, diastereoselective methoxylation, arylation, deallylative methoxylation. Furthermore, we found unique property N-cyano protecting group that enabled α-methoxylation α-substituted second investigation memory chirality decarboxylative We methoxylation oxazolidine thiazolidine derivatives with appropriate N-protecting occurred stereospecific manner even though reaction proceeded through an sp2 planar carbon center. findings demonstrated example chemistry. third chiral azabicyclo-N-oxyls their application organocatalysis oxidative kinetic resolution secondary alcohols. final utilizing generated halogen cations. investigated amino alcohol bromo developed intramolecular C–C bond formation keto amides, bromoiminolactonization α-allyl malonamides, ring expansion allyl It noteworthy most reactions performed undivided cells constant-current conditions, which avoided complicated setup was beneficial large-scale reaction. In addition, some challenges hope research will contribute further construction valuable heterocyclic compounds approach.

Язык: Английский

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Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Chemical Reviews, Год журнала: 2022, Номер 122(21), С. 16110 - 16293

Опубликована: Сен. 16, 2022

In the present review, we discuss recent progress in field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling and catalytic addition reactions. The development advanced systems is aimed at improved catalyst efficiency, reduced loading, better cost environmental concerns, higher selectivity yields. important rise research efforts sustainability green chemistry areas critically assessed. paramount role mechanistic studies a new generation addressed, key achievements, problems, challenges summarized for this field.

Язык: Английский

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Resource Economy by Metallaelectrocatalysis: Merging Electrochemistry and C H Activation

Trends in Chemistry, Год журнала: 2019, Номер 1(1), С. 63 - 76

Опубликована: Март 8, 2019

Язык: Английский

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Single‐Atom Catalysts: A Sustainable Pathway for the Advanced Catalytic Applications

Small, Год журнала: 2021, Номер 17(16)

Опубликована: Фев. 24, 2021

A heterogeneous catalyst is a backbone of modern sustainable green industries; and understanding the relationship between its structure properties key for advancement. Recently, many upscaling synthesis strategies development variety respectable control atomically precise catalysts are reported explored various important applications in catalysis energy environmental remediation. Precise atomic-scale has allowed to significantly increase activity, selectivity, some cases stability. This approach proved be relevant related technologies such as fuel cell, chemical reactors organic synthesis, Therefore, this review aims critically analyze recent progress on single-atom (SACs) application oxygen reduction reaction, evolution hydrogen and/or electrochemical transformations. Finally, opportunities that may open up future summarized, along with suggesting new possible exploitation SACs.

Язык: Английский

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3d metallaelectrocatalysis for resource economical syntheses

Chemical Society Reviews, Год журнала: 2020, Номер 49(13), С. 4254 - 4272

Опубликована: Янв. 1, 2020

This review summarizes key developments in 3d metallaelectrocatalysis the context of resource economy molecular syntheses.

Язык: Английский

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Organic Electrosynthesis: Applications in Complex Molecule Synthesis

ChemElectroChem, Год журнала: 2019, Номер 6(16), С. 4067 - 4092

Опубликована: Май 23, 2019

Abstract Organic electrosynthesis is an enabling and sustainable technology, which constitutes a rapidly expanding field of research. Electrochemical approaches serve as convenient green alternatives to stoichiometric toxic chemical redox agents. Electrosynthesis promising platform for harnessing the unique reactivity profiles radical intermediates, expediting development new reaction manifolds. This Review highlights both anodic cathodic methods construction various kinds complex molecules.

Язык: Английский

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Nickel‐Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry

Angewandte Chemie International Edition, Год журнала: 2019, Номер 58(15), С. 5033 - 5037

Опубликована: Фев. 8, 2019

Transition-metal-catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition-metal-catalyzed thiolation of bromides and chlorides typically requires the use strong base under elevated reaction temperature. Herein, we report first examples nickel-catalyzed electrochemical in absence an external at room temperature using undivided cells.

Язык: Английский

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Electrophotocatalytic Undirected C−H Trifluoromethylations of (Het)Arenes

Chemistry - A European Journal, Год журнала: 2019, Номер 26(15), С. 3241 - 3246

Опубликована: Дек. 25, 2019

Electrophotochemistry has enabled arene C-H trifluoromethylation with the Langlois reagent CF3 SO2 Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for generation radical. electrophotochemistry was carried out in an operationally simple manner, setting stage challenging trifluoromethylations unactivated arenes heteroarenes. robust nature electrophotochemical manifold reflected by wide scope, including electron-rich electron-deficient benzenes, as well naturally occurring Electrophotochemical further achieved flow modular electro-flow-cell equipped in-operando monitoring unit on-line flow-NMR spectroscopy, providing support single electron transfer processes.

Язык: Английский

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