Synthesis of Phenanthridines through Palladium‐Catalyzed Cascade Reaction of 2‐Halo‐<i>N</i>‐Ms‐arylamines with Benzyl Halides/Sulfonates

Yang, Siyi; Han, Wen‐Yong; Zhang, Ding-Lei; Zhou, Xiao‐Jian; Bai, Ming; Cui, Bao‐Dong; Wan, Nan‐Wei; Yuan, Wei‐Cheng; Chen, Yong‐Zheng

doi:10.1002/ejoc.201601608

Cited by 23 publications

(4 citation statements)

References 85 publications

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“…Another variant for the synthesis of these heterocycles consisted in a nucleophilic substitution/C–H activation/palladium-catalyzed aromatization cascade reaction between readily available 2-halo- N -mesyl-arylamines and benzyl halides/sulfonates under harsh conditions . In this transformation, the classical amine reaction occurred at the beginning of the domino sequence.…”

Section: Discussionmentioning

confidence: 99%

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

2019

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The chemistry of palladium complexes has no limits. Many domino processes (even multicomponent) are continuously appearing in the literature. Carbocyclic and heterocyclic molecules are efficiently prepared under the atom economy principle using the smallest amount of the catalyst. The importance of the applications in many scientific areas of all these cyclic skeletons made this general methodology much more attractive.

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Section: Discussionmentioning

confidence: 99%

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

2019

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“…A variety of spiro[oxindole-3,5′-pyrrolo[2,1- a ]isoquinolines] 194 were produced with yields as high as 92% using this approach. 76…”

Section: Synthesis Of Six-membered Ringsmentioning

confidence: 99%

ortho-Halobenzyl Halides as Precursors for the Synthesis of Five- to Nine-Membered Ring Structures Employing Transition Metals as Catalysts

Aljaar,

Malakar,

Shtaiwi

et al. 2024

Synthesis

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This review immerses the multifaceted usefulness of o-halobenzyl halides as a pivotal substrates for the engineering of five- to nine-membered cyclic structures with the aid of transition metals as catalysts. These privileged entities engaged dual active sites, enabling the combination of both intermolecular benzylation and intramolecular arylation strategies that directs the formation of a diverse repository of cyclic structures. The entrance of transition-metal catalysis in cross-coupling transformations has sparked a revolution in forging aryl-heteroatom bonds, and culminating in the evolution of more potent synthetic methodologies for a wide spectrum of valuable compounds. Furthermore, the associated pharmaceutical and biological attributes of these cyclic structures augment their significance in medicinal chemistry research. This review aims to feature the importance of this synthetic methodology and its far-reaching applications in synthesis.

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“…Phenanthridine was first synthesized from the reaction between benzaldehyde and aniline in 1889 [6], and a number of preparative methods have been reported to date [1,[7][8][9]. However, since most protocols necessitate harsh reaction conditions and/or multi-step reaction sequences from commercially available starting materials [10,11], concise and mild preparation procedures for this important class of compounds are still in high demand [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Vanadium(V) Complex-Catalyzed One-Pot Synthesis of Phenanthridines via a Pictet-Spengler-Dehydrogenative Aromatization Sequence

et al. 2020

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Phenanthridine and its derivatives are important structural motifs that exist in natural products, biologically active compounds, and functional materials. Here, we report a mild, one-pot synthesis of 6-arylphenanthridine derivatives by a sequential cascade Pictet-Spengler-dehydrogenative aromatization reaction mediated by oxovanadium(V) complexes under aerobic conditions. The reaction of 2-(3,5-dimethoxyphenyl)aniline with a range of commercially available aryl aldehydes provided the desired phenanthridine derivatives in up to 96% yield. The ability of vanadium(V) complexes to function as efficient redox and Lewis acid catalysts enables the sequential reaction to occur under mild conditions.

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Synthesis of Phenanthridines through Palladium‐Catalyzed Cascade Reaction of 2‐Halo‐N‐Ms‐arylamines with Benzyl Halides/Sulfonates

Cited by 23 publications

References 85 publications

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

Recent Development in Palladium-Catalyzed Domino Reactions: Access to Materials and Biologically Important Carbo- and Heterocycles

ortho-Halobenzyl Halides as Precursors for the Synthesis of Five- to Nine-Membered Ring Structures Employing Transition Metals as Catalysts

Vanadium(V) Complex-Catalyzed One-Pot Synthesis of Phenanthridines via a Pictet-Spengler-Dehydrogenative Aromatization Sequence

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