A crystalline doubly oxidized carbene

Nature, Год журнала: 2023, Номер 623(7985), С. 66 - 70

Опубликована: Сен. 20, 2023

Язык: Английский

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1H-1,2,3-Triazol-5-ylidenes as Catalytic Organic Single-Electron Reductants

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(5), С. 2933 - 2938

Опубликована: Янв. 22, 2024

Most of the known single-electron reductants are either metal based reagents, used in a stoichiometric amount, or combination an organic species and photocatalyst. Here we report that 1

Язык: Английский

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Redox-Neutral Generation of Iminyl Radicals by N-Heterocyclic Carbene Catalysis: Rapid Access to Phenanthridines from Vinyl Azides

Organic Letters, Год журнала: 2022, Номер 24(32), С. 5913 - 5917

Опубликована: Авг. 4, 2022

An N-heterocyclic carbene-catalyzed oxidant-, metal- and light-free iminyl radical generation pathway stemming from the reaction of vinyl azide α-bromo ester is uncovered. This newly developed methodology successfully applied to redox-neutral construction a number diversified phenanthridine derivatives with nice functional group compatibility. Insights mechanism study reveal that this NHC-catalyzed transformation potentially proceeds through an alkyl addition-initiated HAS process, as active intermediate.

Язык: Английский

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Divergent Construction of Heterocycles by SOMOphilic Isocyanide Insertion under N-Heterocyclic Carbene Catalysis

Organic Letters, Год журнала: 2022, Номер 24(41), С. 7654 - 7658

Опубликована: Окт. 11, 2022

A variety of phenanthridines are rapidly constructed by an N-heterocyclic carbene (NHC)-catalyzed SOMOphilic isocyanide insertion-initiated homolytic aromatic substitution-type radical cyclization in the absence any light, transition metals, and external oxidants. The aldehyde-free, scalable, operationally simple protocol tolerates diverse functionalized biaryl isonitriles activated α-halides. Moreover, it can be further applied to divergent construction other N-heterocycles. Preliminary mechanistic studies disclose that NHC-derived cation intermediate is possibly involved.

Язык: Английский

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NHC-Catalyzed Regioselective Intramolecular Radical Cyclization Reaction for the Synthesis of Benzazepine Derivatives

Organic Letters, Год журнала: 2023, Номер 25(32), С. 6072 - 6076

Опубликована: Авг. 8, 2023

A novel and efficient strategy for the synthesis of a series structurally interesting benzazepine derivatives via an N-heterocyclic carbene-catalyzed regioselective intramolecular radical cyclization has been developed. This protocol features good regioselectivity, functional-group compatibility, wide substrate scope, providing transition-metal- oxidant-free pathway to access seven-membered rings under mild reaction conditions. Additionally, further transformation benzazepines large-scale experiment were also conducted.

Язык: Английский

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Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines

Organic Letters, Год журнала: 2022, Номер 24(50), С. 9243 - 9247

Опубликована: Дек. 14, 2022

A number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed insertion into biaryl isonitriles, thus leading to the rapid assembly a variety diversely functionalized 6-cyanoalkyl phenanthridines. preliminary mechanism study revealed that single-electron transfer radical process was possibly involved.

Язык: Английский

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

ChemistryOpen, Год журнала: 2024, Номер unknown

Опубликована: Июль 11, 2024

Abstract This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. compound a carbon has been used primarily only as radical initiator in atom transfer polymerization (ATRP) reactions. However, recent development photo‐radical reactions (around 2010), research on use alkyl precursors became popular 2012). As more examples were reported, studied not radicals but also for their applications organometallic and ionic That is, act nucleophiles well electrophiles. The carbonyl group is attractive because it allows skeleton to be converted after reaction, being applied total synthesis. In our survey until 2022, can perform full range necessary synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific asymmetric α‐Bromocarbonyl have created new trend alkylation, which then had limited reaction patterns focuses how chemistry.

Язык: Английский

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Photoinduced Cerium‐Mediated Decarboxylative Alkylation Cascade Cyclization of N‐arylacrylamides and N‐acryl‐2‐aryl benzimidazoles

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(8)

Опубликована: Фев. 28, 2023

Abstract A mild and versatile cerium‐mediated decarboxylative strategy for sequential alkylation/cyclization was developed the synthesis of quaternary oxindoles benzimidazo[2,1‐ a ]isoquinolin‐6(5 H )‐ones via photoinduced‐LMCT. This operationally simple procedure relies on inexpensive feedstock carboxylic acids as alkyl radical surrogates aerial molecular oxygen terminal oxidant. atom economical protocol showed viability with wide range (1° to 3° acids) coupling partners also allows late‐stage modification pharmaceutically‐important acids. Mechanistic studies revealed reaction follow pathway, while event studied by in situ FTIR.

Язык: Английский

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Construction of all-carbon quaternary center by NHC-catalyzed Heck-type C–H tertiary alkylation

Tetrahedron Chem, Год журнала: 2025, Номер unknown, С. 100124 - 100124

Опубликована: Фев. 1, 2025

Язык: Английский

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1,2-Aminoalkylacylation of styrenes by cooperative NHC/photoredox dual catalysis

Synthetic Communications, Год журнала: 2025, Номер unknown, С. 1 - 9

Опубликована: Апрель 3, 2025

Язык: Английский

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