Nitrogen-Centered Radicals in Functionalization of sp² Systems: Generation, Reactivity, and Applications in Synthesis

Chemical Reviews, Год журнала: 2022, Номер 122(9), С. 8181 - 8260

Опубликована: Март 14, 2022

The chemistry of nitrogen-centered radicals (NCRs) has plentiful applications in organic synthesis, and they continue to expand as our understanding these reactive species increases. utility intermediates is demonstrated the recent advances C–H amination (di)amination alkenes. Synthesis previously challenging structures can be achieved by efficient functionalization sp2 moieties without prefunctionalization, allowing for faster more streamlined synthesis. This Review addresses generation, reactivity, application NCRs, including, but not limited to, iminyl, aminyl, amidyl, aminium species. Contributions from early discovery up most examples have been highlighted, covering radical initiation, thermolysis, photolysis, and, recently, photoredox catalysis. Radical-mediated intermolecular (hetero)arenes occur with a variety complex amine precursors, generating aniline derivatives, an important class drug development. Functionalization olefins achievable high anti-Markovnikov regioselectivity allows access difunctionalized when intermediate carbon are trapped. Additionally, reactivity NCRs harnessed rapid construction N-heterocycles such pyrrolidines, phenanthridines, quinoxalines, quinazolinones.

Язык: Английский

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Electrochemical multicomponent synthesis of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions

Green Chemistry, Год журнала: 2021, Номер 23(11), С. 3950 - 3954

Опубликована: Янв. 1, 2021

An electrochemical multicomponent reaction was established under catalyst-, chemical-oxidant-free and mild conditions, which provides an eco-friendly simple protocol for constructing 4-selanylpyrazoles from easily available raw materials with high yields.

Язык: Английский

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Recent advances in visible-light-mediated organic transformations in water

Green Chemistry, Год журнала: 2020, Номер 23(1), С. 232 - 248

Опубликована: Дек. 11, 2020

Water is a green reaction medium, while visible light represents renewable, clean, and abundant energy source. The recent advances in visible-light-mediated organic transformations water are summarized.

Язык: Английский

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Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Год журнала: 2021, Номер 42(11), С. 1921 - 1943

Опубликована: Авг. 30, 2021

Язык: Английский

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Recent developments in the difunctionalization of alkenes with C–N bond formation

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(18), С. 5206 - 5228

Опубликована: Янв. 1, 2021

Various alkene difunctionalization reactions involving nitridization, diamination, azidation, oxyamination, carboamination, aminohalogenation, and nitration are introduced in this review.

Язык: Английский

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Recent advances in transition-metal-free trifluoromethylation with Togni's reagents

Organic Chemistry Frontiers, Год журнала: 2021, Номер 9(4), С. 1152 - 1164

Опубликована: Дек. 16, 2021

Transition-metal-free trifluoromethylations have attracted significant research interest driven by the increasing importance of CF 3 -containing compounds.

Язык: Английский

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Metal-Free Photosynthesis of Alkylated Benzimidazo[2,1-a]isoquinoline-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones in PEG-200

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(13), С. 9055 - 9066

Опубликована: Июнь 23, 2021

A visible-light-induced decarboxylation reaction was developed for the synthesis of alkylated benzimidazo[2,1-a]isoquinoline-6(5H)-ones and indolo[2,1-a]isoquinolin-6(5H)-ones under metal-free conditions. Impressively, metal catalysts traditionally volatile organic solvents could be effectively avoided.

Язык: Английский

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Visible-Light-Mediated Synthesis of Thio-Functionalized Pyrroles

Organic Letters, Год журнала: 2022, Номер 24(10), С. 1918 - 1923

Опубликована: Март 7, 2022

An inimitable illustration of the green-light-induced synthesis thio-functionalized pyrroles has been established using β-ketodinitriles and thiophenols as reacting partners eosin Y photocatalyst. Large-scale some useful synthetic modifications are also demonstrated.

Язык: Английский

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Metal-Free Photoinduced Hydrocyclization of Unactivated Alkenes toward Ring-Fused Quinazolin-4(3H)-ones via Intermolecular Hydrogen Atom Transfer

Organic Letters, Год журнала: 2023, Номер 25(10), С. 1683 - 1688

Опубликована: Март 8, 2023

A visible-light-induced hydrocyclization of unactivated alkenes was developed using 3CzClIPN as the photocatalyst to generate substituted α-methyldeoxyvasicinones and α-methylmackinazolinones in moderate good yields. An intermolecular hydrogen atom transfer with THF source involved. Mechanism studies indicated that intramolecular addition situ formed aminal radical alkene generated polycyclic quinazolinone.

Язык: Английский

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Nitrile biosynthesis in nature: how and why?

Natural Product Reports, Год журнала: 2024, Номер 41(4), С. 649 - 671

Опубликована: Янв. 1, 2024

Natural nitriles comprise a small set of secondary metabolites which however show intriguing chemical and functional diversity.

Язык: Английский

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