Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations

Chemical Communications, Год журнала: 2019, Номер 55(38), С. 5408 - 5419

Опубликована: Янв. 1, 2019

In this review, the recent advances of application 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a photoredox catalyst in past three years (2016–2018) for various organic reactions are summarized.

Язык: Английский

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Visible light-driven organic photochemical synthesis in China

Science China Chemistry, Год журнала: 2018, Номер 62(1), С. 24 - 57

Опубликована: Дек. 21, 2018

Язык: Английский

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Organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis

Chemical Society Reviews, Год журнала: 2021, Номер 50(13), С. 7587 - 7680

Опубликована: Янв. 1, 2021

Organic compounds that show Thermally Activated Delayed Fluorescence (TADF) have become wildly popular as next generation emitters in organic light-emitting diodes (OLEDs), but since 2016, received significant and increasing attention photocatalysts.

Язык: Английский

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Radical Carboxylative Cyclizations and Carboxylations with CO₂

Accounts of Chemical Research, Год журнала: 2021, Номер 54(10), С. 2518 - 2531

Опубликована: Май 6, 2021

ConspectusCarbon dioxide (CO2) is not only a greenhouse gas and common waste product but also an inexpensive, readily available, renewable carbon resource. It important one-carbon (C1) building block in organic synthesis for the construction of valuable compounds. However, its utilization challenging owing to thermodynamic stability kinetic inertness. Although significant progress has been achieved, many limitations remain this field with regard substrate scope, reaction system, activation strategies.Since 2015, our group focused on CO2 synthesis. We are interested vast possibilities radical chemistry, although high reactivity radicals presents challenges controlling selectivity. hope develop highly useful transformations involving by achieving balance selectivity under mild conditions. Over past 6 years, we along other experts have disclosed radical-type carboxylative cyclizations carboxylations using CO2.We initiated research realizing Cu-catalyzed oxytrifluoromethylation allylamines heteroaryl methylamines generate 2-oxazolidones various precursors. Apart from Cu catalysis, visible-light photoredox catalysis powerful method achieve efficient cyclization. In these cases, single-electron-oxidation-promoted C–O bond formation between benzylic carbamates key step.Since carboxylic acids exist widely natural products bioactive drugs serve as bulk chemicals industry, realized further visible-light-promoted construct such chemicals. achieved selective umpolung imines, enamides, tetraalkylammonium salts, oxime esters successive single-electron-transfer (SSET) reduction. Using strategy, dearomative arylcarboxylation indoles CO2. addition incorporation 1 equiv per substrate, recently developed photoredox-catalyzed dicarboxylation alkenes, allenes, (hetero)arenes via SSET reduction, which allows two molecules into compounds diacids polymer precursors.In two-electron CO2, sought new strategies realize single-electron Inspired hypothetical electron-transfer mechanism iron–sulfur proteins, visible-light-driven thiocarboxylation alkenes catalytic iron salts promoters. The in-situ-generated Fe/S complexes likely able reduce anion, could react give stabilized radical. Moreover, charge-transfer complex (CTC) thiolate acrylate/styrene hydrocarboxylation generation or alkene anion. On basis novel CTC, organocatalytic Hantzsch ester effective reductant.

Язык: Английский

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Reductive radical-polar crossover: traditional electrophiles in modern radical reactions

Chemical Science, Год журнала: 2019, Номер 10(36), С. 8285 - 8291

Опубликована: Янв. 1, 2019

The concept of reductive radical-polar crossover (RRPCO) reactions has recently emerged as a valuable and powerful tool to overcome limitations both radical traditional polar chemistry.

Язык: Английский

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Visible-Light-Driven Reductive Carboarylation of Styrenes with CO₂ and Aryl Halides

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(18), С. 8122 - 8129

Опубликована: Апрель 20, 2020

The first example of visible-light-driven reductive carboarylation styrenes with CO2 and aryl halides in a regioselective manner has been achieved. A broad range iodides bromides were compatible this reaction. Moreover, pyridyl halides, alkyl even chlorides also viable method. These findings may stimulate the exploration novel Meerwein arylation-addition reactions user-friendly as radical sources photocatalytic utilization CO2.

Язык: Английский

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Visible-Light-Driven Catalytic Reductive Carboxylation with CO₂

ACS Catalysis, Год журнала: 2020, Номер 10(19), С. 10871 - 10885

Опубликована: Авг. 28, 2020

Carbon dioxide (CO2) is an important C1 source for the generation of carboxylic acids and derivatives. Stoichiometric catalytic carboxylation nucleophiles, including organometallic reagents, with CO2 has been widely investigated. Since many kinds reagents are prepared from electrophiles, transition-metal-catalyzed direct diverse electrophiles attracted much attention high step economy user-friendly protocols. Although significant progress achieved, use stoichiometric metallic or pyrophoric reductants common. The renaissance photochemistry seen numerous efforts devoted to light-driven CO2, which become one most active directions in this field. In Perspective, we summarize recent advances visible-light-driven reductive substrates, such as unsaturated hydrocarbons, organic (pseudo)halides, imines, presence mild electron donors, amines, Hantzsch esters, formates. We highlight mechanisms reactions, can proceed absence a photoredox catalyst dual visible light photoredox/transition metal system. also discuss future field offer some insight into challenges that remain.

Язык: Английский

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Acridinium Salts and Cyanoarenes as Powerful Photocatalysts: Opportunities in Organic Synthesis

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(36), С. 19526 - 19549

Опубликована: Апрель 22, 2021

The use of organic photocatalysts has revolutionized the field photoredox catalysis, as it allows access to reactivities that were traditionally restricted transition-metal photocatalysts. This Minireview reports recent developments in acridinium ions and cyanoarene derivatives synthesis. activation inert chemical bonds well late-stage functionalization biorelevant molecules are discussed, with a special focus on their mechanistic aspects.

Язык: Английский

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4CzIPN-^tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

Journal of the American Chemical Society, Год журнала: 2020, Номер 143(2), С. 964 - 972

Опубликована: Дек. 29, 2020

2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu catalyst, we visible-light-induced proton-coupled electron transfer strategy generation phosphorus-centered radicals, via which wide range phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.

Язык: Английский

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Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis

Nature Communications, Год журнала: 2019, Номер 10(1)

Опубликована: Авг. 9, 2019

Catalytic difunctionalization of alkenes has been an ideal strategy to generate structurally complex molecules with diverse substitution patterns. Although both phosphonyl and carboxyl groups are valuable functional groups, the simultaneous incorporation them via catalytic alkenes, ideally from abundant, inexpensive easy-to-handle raw materials, not realized. Herein, we report phosphonocarboxylation CO2 visible-light photoredox catalysis. This is sustainable, general practical, providing facile access important β-phosphono carboxylic acids, including unnatural α-amino acids. Diverse enamides, styrenes, enolsilanes acrylates, undergo such reactions efficiently under mild reaction conditions. Moreover, this method represents a rare example redox-neutral H-P(O) compounds, diaryl- dialkyl- phosphine oxides phosphites. Importantly, these transition-metal-free also feature low catalyst loading, high regio- chemo-selectivities, good group tolerance, easy scalability potential for product derivatization.

Язык: Английский

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