Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation

Chemical Communications, Год журнала: 2021, Номер 57(47), С. 5758 - 5761

Опубликована: Янв. 1, 2021

Mild and efficient C–H functionalization of tryptophan tryptophan-containing peptides with activated α-bromo-carbonyl compounds under visible-light irradiation is described.

Язык: Английский

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N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Июнь 10, 2022

Abstract N- functionalized aziridines, which are both useful intermediates and important synthetic targets, can be envisioned as arising from the addition of nitrenes ( i.e ., NR fragments) to olefinic substrates. The exceptional reactivity most nitrenes, in particular with respect unimolecular decomposition, prevents general application nitrene-transfer synthesis N -functionalized aziridines. Here we demonstrate -aryl aziridine via 1) olefin aziridination -aminopyridinium reagents afford -pyridinium aziridines followed by 2) Ni-catalyzed C–N cross-coupling aryl boronic acids. also participate ring-opening chemistry a variety nucleophiles 1,2-aminofunctionalization products. Mechanistic investigations indicate proceeds noncanonical mechanism involving initial opening promoted bromide counterion Ni catalyst, cross-coupling, finally reclosure. Together, these results provide new opportunities achieve selective incorporation generic nitrene equivalents organic molecules.

Язык: Английский

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Recent Applications of Trifluoromethanesulfonic Anhydride in Organic Synthesis

Angewandte Chemie International Edition, Год журнала: 2022, Номер 62(10)

Опубликована: Дек. 21, 2022

Abstract Trifluoromethanesulfonic anhydride has been widely used in synthetic organic chemistry, not only for the conversion of various oxygen‐containing compounds to triflates, but also electrophilic activation and further amides, sulfoxides, phosphorus oxides. In recent years, utilization Tf 2 O as an activator nitrogen‐containing heterocycles, nitriles nitro groups become a promising tool development new valuable methods with considerable success. addition, efficient radical trifluoromethylation trifluoromethylthiolation reagent due contained SO CF 3 fragment, significant progress made this area. This review summarizes applications above two aspects, aims illustrate role potential application synthesis.

Язык: Английский

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Traceless Benzylic C−H Amination via BifunctionalN‐Aminopyridinium Intermediates

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(28)

Опубликована: Апрель 28, 2022

C-H amination reactions provide the opportunity to streamline synthesis of nitrogen-containing organic small molecules. The impact intermolecular methods, however, is currently limited frequent requirement for amine precursors bear activating groups, such as N-sulfonyl substituents, that are both challenging remove and not useful synthetic handles subsequent derivatization. Here, we introduce traceless nitrogen activation amination-which enables application selective chemistry preparation diverse N-functionalized products-via sequential benzylic N-aminopyridylation followed by Ni-catalyzed C-N cross-coupling with aryl boronic acids. Unlike many access protected amines, current method installs an easily diversifiable handle serves a lynchpin amination, deaminative N-N functionalization sequences.

Язык: Английский

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Photochemical C(sp²)−H Pyridination via Arene–Pyridinium Electron Donor–Acceptor Complexes

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(46)

Опубликована: Сен. 14, 2022

This report describes the development of a photochemical method for C(sp

Язык: Английский

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Green and fast 2-aryloxylation/amination of quinolines

Green Chemistry, Год журнала: 2024, Номер 26(8), С. 4659 - 4664

Опубликована: Янв. 1, 2024

The direct C2-H functionalization of quinolines has always been a widely concerned area. Herein we report rapid and eco-friendly synthesis 2-aroxyquinolines 2-aminoquinolines through deoxygenative quinoline N -oxides.

Язык: Английский

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Palladium‐Catalyzed Site‐Selective C─H Alkoxylation Using Biorelevant Heterocyclic Directing Groups

ChemistrySelect, Год журнала: 2025, Номер 10(2)

Опубликована: Янв. 1, 2025

Abstract This study introduces a novel palladium‐catalyzed alkoxylation method via C─H activation, utilizing an intrinsic, weakly coordinating directing group (DG) derived from bioactive molecules. approach is particularly relevant for the pharmaceutical and chemical industries, offering versatile tool functionalizing complex compounds. The success site selectivity of this are determined by choice catalytic systems reaction conditions, including catalyst, ligand, solvent, temperature. substrate scope demonstrates broad applicability, modifying scaffolds, highlighting method's generalizability. protocol provides promising route altering compounds other critical products with exceptional regioselectivity. discovery intrinsic DG, combined ability to fine‐tune positions methodology as significant advancement functionalization processes in applications, paving way further exploration these fields.

Язык: Английский

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Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Язык: Английский

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Pyridiniumsalze als redoxaktive Reagenzien zur Übertragung funktioneller Gruppen

Angewandte Chemie, Год журнала: 2019, Номер 132(24), С. 9350 - 9366

Опубликована: Окт. 10, 2019

Abstract In diesem Aufsatz sind die jüngsten Fortschritte beim Verständnis und Design von N‐funktionalisierten Pyridiniumsalzen als redoxaktivierte Einelektronentransfer‐Reagenzien zur Übertragung funktioneller Gruppen zusammengefasst. Anhand einer Auswahl an repräsentativen Methoden werden Reaktivität grundlegende in sich rasch entwickelnden Bereich diskutiert. Diese Reagenzien weisen zwei grundsätzlich divergierende Reaktionspfade auf: homolytische Fragmentierung Freisetzung des N‐gebundenen Substituenten entsprechendes Radikal oder eine alternative, heterolytische eines radikalischen Pyridiniumkations. Die elementaren Schritte der durch Einelektronentransfer induzierten kritisch

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S_NAr and C–H Amination of Electron Rich Arenes with Pyridine as a Nucleophile Using Photoredox Catalysis

Organic Letters, Год журнала: 2021, Номер 23(13), С. 5213 - 5217

Опубликована: Июнь 23, 2021

This report describes the development of two photocatalytic methods for pyridination electron rich arenes. First, an SNAr-type reaction between aryl halides and pyridine is developed optimized. transformation affords selective substitution C(sp2)–halogen over C(sp2)–OR bonds to afford arylpyridinium products under anaerobic conditions. Under complementary aerobic conditions, analogous substrates are shown undergo oxidative C(sp2)–H pyridination.

Язык: Английский

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