Photoinduced Difunctionalization of Diazenes Enabled by N–N Radical Coupling

Jiang, Yu-Shi; Li, Shan-Shan; Luo, Xue-Ling; Chen, Li-Ning; Chen, Dan-Na; Xia, Peng-Ju

doi:10.1021/acs.orglett.3c02533

Cited by 14 publications

(1 citation statement)

References 48 publications

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“…The radical coupling reaction is a straightforward strategy for bond formation. Very recently, the Xia group reported a photoinduced difunctionalization of diazenes in which a rare N(sp 3 )–N(sp 2 ) radical coupling was involved (Scheme ). In this reaction, benzophenone oxime esters 70 were introduced as the difunctionalization source, which has been proven to initiate transient radicals and persistent benzophenone imine radicals in photocatalytic systems.…”

Section: Catalytic N–n Bond Formationmentioning

confidence: 99%

Recent Advances in Catalytic Nitrogen–Nitrogen Bond Formation Reactions

Hu,

Wu,

Gao

et al. 2024

ACS Catal.

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The lack of effective strategies for direct construction of nitrogen−nitrogen bonds has hampered developments in the synthesis and application of molecules containing hydrazine or azo motifs. Attracted by their properties both in material science and in medicinal chemistry, more and more attention has been drawn to this area, resulting in fast growth in the design and synthesis of azaheterocycles and substituted hydrazines. This review focuses on efficient catalytic approaches toward the formation of N−N and N�N bonds through different strategies, including oxidative dehydrogenation, nitrene-transfer reaction, reductive coupling, and some other recently developed methods.

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Section: Catalytic N–n Bond Formationmentioning

confidence: 99%

Recent Advances in Catalytic Nitrogen–Nitrogen Bond Formation Reactions

Hu,

Wu,

Gao

et al. 2024

ACS Catal.

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Selective 1,2‐Carboimination of Isothiocyanates to Access S‐Substituted Isothioureas via Energy Transfer Catalysis

Chen,

Liang,

Luo

et al. 2024

Adv Synth Catal

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Herein, we introduce a novel method for the synthesis of S‐substituted isothiourea compounds via the selective 1,2‐carboimination between oxime esters as bifunctional reagents and the C=S bond of isothiocyanates under visible‐light catalysis. This approach deviates from conventional methods by precisely modulating the substrate electronics to selectively functionalize the C=S bond of isothiocyanates over the C=N bond, eliminating the need for strong bases and high temperatures and bypassing the formation of thiourea intermediates. Consequently, this protocol enables the efficient one‐step synthesis of S‐alkyl isothioureas, with featuring mild reaction conditions, operational simplicity and broad substrate scope.

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Oxidative N−N Bond Formation Versus the Curtius Rearrangement

Hohenadel,

Ebel,

Oppel

et al. 2024

Chemistry A European J

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The oxidative formation of N–N bonds from primary amides has been recently reported and then retracted in the journal Nature Communications by Kathiravan, Nicholls, and coauthors, utilizing a hypervalent iodane reagent. Unfortunately, the authors failed to recognize the Curtius reaction taking place under the described reaction conditions. Thus, the claimed N–N coupling products were not formed. Instead, the Curtius rearrangement urea coupling products were obtained. We demonstrate this herein by means of NMR and x‐ray analysis, as well as with the support of an alternative synthetic route.

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Photoinduced Difunctionalization of Diazenes Enabled by N–N Radical Coupling

Cited by 14 publications

References 48 publications

Recent Advances in Catalytic Nitrogen–Nitrogen Bond Formation Reactions

Recent Advances in Catalytic Nitrogen–Nitrogen Bond Formation Reactions

Selective 1,2‐Carboimination of Isothiocyanates to Access S‐Substituted Isothioureas via Energy Transfer Catalysis

Oxidative N−N Bond Formation Versus the Curtius Rearrangement

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