Photo‐Induced Construction of <i>N</i>‐Aryl Amides by Fe Catalysis

Mei, Yong-Kang; Min, Xiang‐Ting; Guo, Shiyu; Liu, Changhui; Zhang, Xiang‐Xin; Ji, Ding‐Wei; Wan, Boshun

doi:10.1002/ejoc.202200043

Cited by 7 publications

(3 citation statements)

References 54 publications

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“…73 Chen and co-workers reported a photoinduced iron-catalyzed electrophilic amidation for the construction of N-aryl amides (Scheme 15D). 74 Noel, Alcaźar, and co-workers demonstrated C(sp 2 )-C(sp 3 ) Kumada-Corriu cross-coupling reactions in flow, promoted by visible light in the presence of [Fe(acac) 3 ], an NHC ligand (SIPr-HCl = 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride), and Grignard reagents (Scheme 15E). 75 Yu and co-workers proposed a thiocarboxylation of styrenes, in the presence of FeCl 3 , under visible-light irradiation (Scheme 15F).…”

Section: Other In Situ-formed Fe Complexes (Non-vlih)mentioning

confidence: 99%

“…Xia’s group investigated the blue-light-driven aminoselenation of alkenes employing FeBr 3 as a precatalyst in air (Scheme C) . Chen and co-workers reported a photoinduced iron-catalyzed electrophilic amidation for the construction of N -aryl amides (Scheme D) . Noël, Alcázar, and co-workers demonstrated C(sp 2 )-C(sp 3 ) Kumada-Corriu cross-coupling reactions in flow, promoted by visible light in the presence of [Fe(acac) 3 ], an NHC ligand (SIPr-HCl = 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride), and Grignard reagents (Scheme E) .…”

Section: In Situ-generated Photoreactive Iron Complexesmentioning

confidence: 99%

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Iron Photoredox Catalysis–Past, Present, and Future

et al. 2023

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Photoredox catalysis of organic reactions driven by iron has attracted substantial attention throughout recent years, due to potential environmental and economic benefits. In this Perspective, three major strategies were identified that have been employed to date to achieve reactivities comparable to the successful noble metal photoredox catalysis: (1) Direct replacement of a noble metal center by iron in archetypal polypyridyl complexes, resulting in a metal-centered photofunctional state. (2) In situ generation of photoactive complexes by substrate coordination where the reactions are driven via intramolecular electron transfer involving charge-transfer states, for example, through visible-light-induced homolysis. (3) Improving the excited-state lifetimes and redox potentials of the charge-transfer states of iron complexes through new ligand design. We seek to give an overview and evaluation of recent developments in this rapidly growing field and, at the same time, provide an outlook on the future of iron-based photoredox catalysis.

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Section: Other In Situ-formed Fe Complexes (Non-vlih)mentioning

confidence: 99%

Section: In Situ-generated Photoreactive Iron Complexesmentioning

confidence: 99%

Iron Photoredox Catalysis–Past, Present, and Future

et al. 2023

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“…Therefore, the development of more environmentally friendly and more atom-economical methods is still in great need. As our ongoing interest in photocatalysis, we herein developed visible-light-induced C–S bond construction by employing inorganic sulfides as both a donor of an EDA complex and a sulfur donor. Through simple control of the type of sulfides and the photoredox catalyst, (hetero)aryl halides were selectively transformed into (hetero)aryl sulfides and (hetero)aryl disulfides in high efficiency (Scheme D).…”

Section: Introductionmentioning

confidence: 99%

Selective C–S Bond Constructions Using Inorganic Sulfurs via Photoinduced Electron Donor–Acceptor Activation

Yang

Sun

et al. 2022

J. Org. Chem.

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By complementing traditional transition metal catalysis, photoinduced catalysis has emerged as a versatile and sustainable way to achieve carbon−heteroatom bond formation. This work discloses a visible-light-induced reaction for the formation of a C−S bond from aryl halides and inorganic sulfuration agents via electron donor−acceptor (EDA) complex photocatalysis. Divergent formations of organic sulfide and disulfide have been demonstrated under mild conditions. Preliminary mechanistic studies suggest that visible-light-induced intracomplex charge transfer within the monosulfide-anion-containing EDA complex permits the C−S bond construction reactivity.

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S_N2 Reaction at the Amide Nitrogen Center Enables Hydrazide Synthesis

Fang,

Luo,

Wang

et al. 2024

Angewandte Chemie

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Nucleophilic substitutions are fundamentally important transformations in synthetic organic chemistry. Despite the substantial advances in bimolecular nucleophilic substitutions (SN2) at saturated carbon centers, analogous SN2 reaction at the amide nitrogen atom remains extremely limited. Here we report an SN2 substitution method at the amide nitrogen atom with amine nucleophiles for nitrogen−nitrogen (N−N) bond formation that leads to a novel strategy toward biologically and medicinally important hydrazide derivatives. We found the use of sulfonate‐leaving groups at the amide nitrogen atom played a pivotal role in the reaction. This new N−N coupling reaction allows the use of O‐tosyl hydroxamates as electrophiles and readily available amines, including acyclic aliphatic amines and saturated N‐heterocycles as nucleophiles. The reaction features mild conditions, broad substrate scope (>80 examples), excellent functional group tolerability, and scalability. The method is applicable to late‐stage modification of various approved drug molecules, thus enabling complex hydrazide scaffold syntheses.

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Photo‐Induced Construction of N‐Aryl Amides by Fe Catalysis

Cited by 7 publications

References 54 publications

Iron Photoredox Catalysis–Past, Present, and Future

Iron Photoredox Catalysis–Past, Present, and Future

Selective C–S Bond Constructions Using Inorganic Sulfurs via Photoinduced Electron Donor–Acceptor Activation

S_N2 Reaction at the Amide Nitrogen Center Enables Hydrazide Synthesis

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Photo‐Induced Construction of N‐Aryl Amides by Fe Catalysis

Cited by 7 publications

References 54 publications

Iron Photoredox Catalysis–Past, Present, and Future

Iron Photoredox Catalysis–Past, Present, and Future

Selective C–S Bond Constructions Using Inorganic Sulfurs via Photoinduced Electron Donor–Acceptor Activation

SN2 Reaction at the Amide Nitrogen Center Enables Hydrazide Synthesis

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Product

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S_N2 Reaction at the Amide Nitrogen Center Enables Hydrazide Synthesis