Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C H/N O bond activation

Lin, Wei; Hu, Xiuxiu; Zhuang, Cangwei; Wang, Yazhen

doi:10.1016/j.tet.2019.04.039

Cited by 16 publications

(2 citation statements)

References 58 publications

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“…The structure of 34 was unambiguously proved by single crystal X-ray analysis, showing an unprecedented 10 conjugation framework. In sharp contrast to our Fe/Al catalytic system that provided 34 in quantitative yield, the other literature conditions for similar cyclization 38 of oxime or oxime ether employing other metal catalysts such as Co 39 , Mn 40 , Ru 41 , Ir 42 , and Rh 43 , all failed to react. Only one feasible condition was a rhodium-catalyzed condition elegantly developed by You and co-workers 44 , while 20 mol % of rhodium was used with only a moderate yield obtained.…”

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confidence: 81%

Iron-Catalyzed Aza-Annulative π-Extension with Alkynes via C–H Activation using an Oxidative Auxiliary

Zhang,

Fukuma,

Shang

et al. 2024

Preprint

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Aza-annulative π-extension (AAPE) reactions offer a potent pathway to create novel donor-acceptor conjugated materials by integrating an imine moiety into the conjugated system, serving as an electron-accepting unit. However, the affinity of late-transition metals for conjugated π-systems, coupled with their elevated cost, has posed significant challenges, restricting efficient AAPE reactions on straightforward C–H substrates for developing conjugated new materials. In this study, we unveil an iron-catalyzed C–H activation methodology, facilitating AAPE with diverse internal alkynes and employing oxime ether as both a self-oxidizing auxiliary and nitrogen source, derived seamlessly from accessible carbonyl compounds. The AAPE reaction was enabled by using trisphosphine as a ligand, and isobutyl aluminum(III) catecholate as a base. By using the reaction, we discovered an aza-oxa[5]helicene from dixanthone as a potential circularly polarized luminescence material and two narrow-band-emissive molecules from easily accessible pentacene-6,13-dione and quinacridone, which emit blue and yellow light with high color purity and high fluorescence quantum yield. These findings emphasize the potential of iron-catalyzed C–H activation in expanding the range of donor-acceptor-type conjugated materials for organic electronics.

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confidence: 81%

Iron-Catalyzed Aza-Annulative π-Extension with Alkynes via C–H Activation using an Oxidative Auxiliary

Zhang,

Fukuma,

Shang

et al. 2024

Preprint

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“…The present method showed good control and selectivity over various functional groups, symmetrical and unsymmetrical alkynes (Scheme 104). [124] Based on mechanistic study and previous reports, [78,[125][126][127] a plausible mechanism for the Ir(III)-catalyzed CÀ H annulation of ketoximes was proposed (Scheme 105).…”

Section: Ir-catalyzed Isoquinoline Synthesismentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.

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Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides

Nie

Zeng

et al. 2020

Adv Synth Catal

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A palladium‐catalyzed cyclization of N‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α‐substituted vinyl azide serves as an internal nitrogen source. Also, C−H bond activation and C−N bond cleavage have been realized using hydrazone as directing group.

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Easy access to synthesize isoquinolines from aryl ketoximes and internal alkynes via Iridium (III)-catalyzed C H/N O bond activation

Cited by 16 publications

References 58 publications

Iron-Catalyzed Aza-Annulative π-Extension with Alkynes via C–H Activation using an Oxidative Auxiliary

Iron-Catalyzed Aza-Annulative π-Extension with Alkynes via C–H Activation using an Oxidative Auxiliary

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides

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