Redoxneutrale Mangan(I)‐katalysierte C‐H‐Aktivierung: regioselektive Anellierung mithilfe einer spurlosen dirigierenden Gruppe

Lu, Qingquan; Greßies, Steffen; Cembellín, Sara; Klauck, Felix J. R.; Daniliuc, Constantin G.; Glorius, Frank

doi:10.1002/ange.201707396

Cited by 42 publications

(1 citation statement)

References 85 publications

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“…11 For example, preinstalled DGs require additional steps for pre-functionalization installation and post-functionalization removal, which may not be compatible with sensitive functional groups and may hamper the overall efficacy of the transformation; traceless DGs sometimes need extra steps for their synthesis, which may reduce the possible practicality. 17 In the case of non-covalent interactive DGs, the customization of both the substrate and catalytic ligand with additional pendant sites such as cation/anion, H-bond donor/acceptor, Lewis acid/base, or π-electron system, is required to facilitate the non-covalent interactions. Thus, the introduction of typical suitable functionalities necessitates multistep synthesis and, therefore, cannot be considered as step- and atom-efficient.…”

Section: Table 1 Representative Data Of the Optimizatio...mentioning

confidence: 99%

Benzoxazole or Benzothiazole as an Innate Directing Group for Palladium- and Ruthenium-Catalyzed Complementary C–H Arylation: Functionalization of Biorelevant Heterocyclic Scaffolds

Seth,

Maingle,

Sunny

et al. 2023

Synthesis

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Benzoxazole and benzothiazole moiety have been used as innate directing handles for Pd(II)- and Ru(II)-catalyzed C–H arylation of bio-relevant heterocycles, 2-arylbenzoxazole and 2-arylbenzothiazole with diverse iodoarenes, following a complementarity of palladium-ruthenium catalysts. The induction of σ-donor ligands, such as N,N-dimethylacetamide to Pd(II) catalytic cycle and σ-donor/π-acceptor ligand, such as PPh3 to Ru(II) catalytic cycle enhances the arylation rate significantly and governed by the C–H acidity of C2-aryl ring of 2-arylbenzoxazole/2-arylbenzothiazole. The approaches have a broad substrate scope with respect to coupling partners to accommodate electron-neutral, electron-rich as well as electron-deficient iodoarenes plus C2-aryl unit of 2-arylbenzoxazoles/2-arylbenzothiazoles, exhibit a high degree of siteselectivity at ortho-C–H position, afford only mono-arylated derivatives in decent yields, functional groups tolerant, and applicable to ‘gram-scale’ production.

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Section: Table 1 Representative Data Of the Optimizatio...mentioning

confidence: 99%

Benzoxazole or Benzothiazole as an Innate Directing Group for Palladium- and Ruthenium-Catalyzed Complementary C–H Arylation: Functionalization of Biorelevant Heterocyclic Scaffolds

Seth,

Maingle,

Sunny

et al. 2023

Synthesis

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Rhodium‐Catalyzed Cascade Annulation of Benzimidates and Nitroalkenes for the Synthesis of Difunctionalized Indenes

Chen

Liu

et al. 2019

Adv Synth Catal

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A facile and expeditious protocol for the synthesis of difunctionalized indenes from readily available benzimidates and nitroalkenes through rhodium-catalyzed CÀ H activation and cyclization is reported here. The transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds in moderate to high yields under an ambient atmosphere, providing a straightforward method to access structurally diverse and valuable difunctionalized indene derivatives.

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Manganese‐Catalysed C−H Activation: A Regioselective C−H Alkenylation of Indoles and other (hetero)aromatics with 4‐Hydroxy‐2‐Alkynoates Leading to Concomitant Lactonization

2019

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A manganese-catalyzed CÀ H bond alkenylation of indoles at C2-position with 4-hydroxy-2alkynoates leading to concomitant lactonization under removable directing group strategy has been disclosed. This lactonization strategy exhibits regioselectivity, a broad substrate scope, and a good functional group tolerance furnishing the products in low to high yields. The regioselectivity is guided by the electronic effect of the ester group as well as the steric bulk at the C4-position of the 4-hydroxy-2-alkynoates. After the reaction, the directing group has been readily removed to obtain NÀ H free indole. Scheme 1. Comparision of prevoius works with this work. Scheme 2. Substrate scope of indole and pyrrole derivatives.Scheme 4. Substrate scope of indole and other (hetero)aromatics compounds. Scheme 5. Scaling-up reaction and synthetic utility.

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Redoxneutrale Mangan(I)‐katalysierte C‐H‐Aktivierung: regioselektive Anellierung mithilfe einer spurlosen dirigierenden Gruppe

Cited by 42 publications

References 85 publications

Benzoxazole or Benzothiazole as an Innate Directing Group for Palladium- and Ruthenium-Catalyzed Complementary C–H Arylation: Functionalization of Biorelevant Heterocyclic Scaffolds

Benzoxazole or Benzothiazole as an Innate Directing Group for Palladium- and Ruthenium-Catalyzed Complementary C–H Arylation: Functionalization of Biorelevant Heterocyclic Scaffolds

Rhodium‐Catalyzed Cascade Annulation of Benzimidates and Nitroalkenes for the Synthesis of Difunctionalized Indenes

Manganese‐Catalysed C−H Activation: A Regioselective C−H Alkenylation of Indoles and other (hetero)aromatics with 4‐Hydroxy‐2‐Alkynoates Leading to Concomitant Lactonization

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