Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations DOI Creative Commons
Toshifumi Dohi, Elghareeb E. Elboray, Kotaro Kikushima

и другие.

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Март 7, 2025

Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl-halide is a crucial step most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling direct (hetero)arylation trapping reagents construction highly functionalized (hetero)arenes benign conditions. strategies for aryl iodides are classified into (a) hypervalent iodoarene followed by functionalization thermal/photochemical conditions, (b) aryl-I bond in presence bases with/without organic catalysts promoters, (c) photoinduced presence/absence organophotocatalysts, (d) electrochemical direct/indirect electrolysis mediated organocatalysts mediators acting as electron shuttles, (e) electrophotochemical redox-active organocatalysts. These modes result exhibiting diverse reactivity formal cations/radicals/anions aryne precursors. coupling these reactive intermediates with leads to facile selective formation C-C C-heteroatom bonds. ecofriendly, inexpensive, functional group-tolerant offer alternatives transition metal-based catalysis.

Язык: Английский

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis DOI
Nicholas E. S. Tay, Dan Lehnherr, Tomislav Rovis

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2487 - 2649

Опубликована: Ноя. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Язык: Английский

Процитировано

361

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds DOI
Fanyang Mo, Di Qiu, Lei Zhang

и другие.

Chemical Reviews, Год журнала: 2021, Номер 121(10), С. 5741 - 5829

Опубликована: Апрель 9, 2021

Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance aryl spanning most disciplines chemical sciences, we review recent development chemistry over past seven years (2013-2020). Special emphasis is put on various new transformations involving generation radical intermediates via thermal, photochemical, and electrochemical means. Recent advances transition metal-catalyzed reactions using also reviewed. Together, these newly developed significantly expand synthetic chemist's repertoire aromatic carbon-carbon carbon-heteroatom bond forming methods precursors, providing powerful tools for synthesis modification complex molecular scaffolds.

Язык: Английский

Процитировано

242

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency DOI
Guglielmo Coppola, Serena Pillitteri, Erik V. Van der Eycken

и другие.

Chemical Society Reviews, Год журнала: 2022, Номер 51(6), С. 2313 - 2382

Опубликована: Янв. 1, 2022

Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.

Язык: Английский

Процитировано

167

Decatungstate-Catalyzed C(sp3)–H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality DOI
Patrick Sarver, Noah B. Bissonnette, David W. C. MacMillan

и другие.

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(26), С. 9737 - 9743

Опубликована: Июнь 23, 2021

Here we report the direct conversion of strong, aliphatic C(

Язык: Английский

Процитировано

118

Radical approaches to C–S bonds DOI
Zijun Wu, Derek A. Pratt

Nature Reviews Chemistry, Год журнала: 2023, Номер 7(8), С. 573 - 589

Опубликована: Июнь 21, 2023

Язык: Английский

Процитировано

54

Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System DOI
Long‐Yong Xie,

Lilin Jiang,

Jia-Xi Tan

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2019, Номер 7(16), С. 14153 - 14160

Опубликована: Июль 15, 2019

A efficient and sustainable approach for the synthesis of 3-alkylquinoxalin-2(1H)-ones has been developed through visible-light-mediated decarboxylative alkylation quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates. This photocatalytic reaction could be conducted at ambient temperature by employing eco-friendly PEG-200 as medium. Various were easily obtained present ruthenium(II) catalytic system, which successfully recycled five times without significant decrease its efficiency.

Язык: Английский

Процитировано

144

Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions DOI

Kai-Jian Liu,

Ji-Hui Deng,

Jie Yang

и другие.

Green Chemistry, Год журнала: 2019, Номер 22(2), С. 433 - 438

Опубликована: Ноя. 26, 2019

The first example of selective oxidation sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established. desired products could be easily collected through recrystallization in large-scale preparation.

Язык: Английский

Процитировано

125

The concept of dual roles design in clean organic preparation DOI
Zhong Cao, Qin Zhu, Ying‐Wu Lin

и другие.

Chinese Chemical Letters, Год журнала: 2019, Номер 30(12), С. 2132 - 2138

Опубликована: Сен. 19, 2019

Язык: Английский

Процитировано

123

Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones DOI
Shuai Liang,

Kamil Hofman,

Marius Friedrich

и другие.

ChemSusChem, Год журнала: 2021, Номер 14(22), С. 4878 - 4902

Опубликована: Сен. 3, 2021

Sulfones play a pivotal role in modern organic chemistry. They are highly versatile building blocks and find various applications as drugs, agrochemicals, or functional materials. Therefore, sustainable access to this class of molecules is great interest. Herein, the goal was provide summary on recent developments field sulfone synthesis. Advances existing limitations traditional approaches towards sulfones were reviewed selected examples. Furthermore, novel emerging technologies for more synthesis future directions discussed.

Язык: Английский

Процитировано

94

A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide DOI
Xinxing Gong, Min Yang, Jin‐Biao Liu

и другие.

Green Chemistry, Год журнала: 2020, Номер 22(6), С. 1906 - 1910

Опубликована: Янв. 1, 2020

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and bromides visible light irradiation at room temperature.

Язык: Английский

Процитировано

91