Durch sichtbares Licht vermittelte Funktionalisierungen von Benzotriazolen, inspiriert durch mechanismusbasiertes Lumineszenz‐ Screening

Teders, Michael; Gómez‐Suárez, Adrián; Pitzer, Lena; Hopkinson, Matthew N.; Glorius, Frank

doi:10.1002/ange.201609393

Cited by 19 publications

(1 citation statement)

References 51 publications

(27 reference statements)

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“…A radical chain mechanism was proposed depending on the reaction conditions employed. First, the radical anion is generated via a single electron transfer (SET) upon blue LED irradiation, followed by a denitrogenation procedure to lead to aryl radical 172 . The addition of the alkyne and aryl radical gives the stabilized radical intermediate 173 and subsequent oxidative and annulation affords the cycloaddition products 170 .…”

Section: Denitrogenative Cyclization Of Benzotriazolesmentioning

confidence: 99%

Synthesis of Heterocycles through Denitrogenative Cyclization of Triazoles and Benzotriazoles

Zhang

2020

Chemistry A European J

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During the past few decades, there has been considerable growth in the development of denitrogenative reactions of triazole skeletons to construct valuable cyclic compounds, particularly heterocycles. Despite the inherent difficulty of the ring‐opening of triazole derivatives, many novel and efficient approaches have arisen in this area mainly with the use of transition metal (such as rhodium, palladium, silver, copper) catalysis, photolysis, or free radical mediated reactions. Generally, these procedures begin with the ring‐opening of 1,2,3‐triazoles or benzotriazoles followed by N2 extrusion and subsequent diverse transformations, which enable the rapid synthesis of various heterocycles in a single step. To avoid overlap with other related reviews, this minireview covers the recent advances in the denitrogenative cyclization of 1,2,3‐triazoles since 2016 and the denitrogenative cyclization of benzotriazoles since 2012.

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Section: Denitrogenative Cyclization Of Benzotriazolesmentioning

confidence: 99%

Synthesis of Heterocycles through Denitrogenative Cyclization of Triazoles and Benzotriazoles

Zhang

2020

Chemistry A European J

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Recent Advances in C–B Bond Formation through a Free Radical Pathway

Yan

Huang

2017

Adv Synth Catal

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The development of a methodology for the preparation of arylboronic acids or arylboronates is of significant interest to organic chemists. Classical synthetic methods to prepare these organoboron compounds are based on the reaction of Grignard or lithium reagents with trialkyl borates. In the past few decades, the transition‐ metal‐catalyzed borylation of aryl halides, or pseudohalides, and C–H bonds of hydrocarbons has been a powerful tool for the synthesis of arylboronates in modern organic synthesis. These transformations are generally considered to proceed via organometallic intermediates generated by oxidative addition or transmetalation processes from the boron reagent. Several reviews on this type of borylation catalyzed by transition metals have been published in the literature. Interestingly, there has been a novel recognition that the boron reagent can participate in free‐radical coupling via the homolytic cleavage of the boron‐boron bond in recent years. In this review, recent advances in this new area of boron chemistry are summarized and the reaction mechanisms are also discussed.

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Durch sichtbares Licht vermittelte Deaminierung zur Erzeugung von Alkylradikalen

2017

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Eine Deaminierungsstrategie fürd ie durch sichtbares Licht vermittelte Erzeugungv on Alkylradikalen aus redoxaktivierten primären Amin-Vorstufen wird beschrieben. Häufig vorkommende und preiswerte primäre Amine,e inschließlich der Aminosäuren, wurden in einem Schritt in redoxaktive Pyridiniumsalzeund anschließend in Alkylradikale durch Umsetzung mit einem angeregten Photokatalysator umgesetzt. Das Potenzial dieses Protokolls fürS ynthesen wurde durch die einfach durchzuführende Alkylierung einer Anzahl von Heteroarenen unter milden Bedingungen nachgewiesen.

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Durch sichtbares Licht vermittelte Funktionalisierungen von Benzotriazolen, inspiriert durch mechanismusbasiertes Lumineszenz‐ Screening

Cited by 19 publications

References 51 publications

Synthesis of Heterocycles through Denitrogenative Cyclization of Triazoles and Benzotriazoles

Synthesis of Heterocycles through Denitrogenative Cyclization of Triazoles and Benzotriazoles

Recent Advances in C–B Bond Formation through a Free Radical Pathway

Durch sichtbares Licht vermittelte Deaminierung zur Erzeugung von Alkylradikalen

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