Substrate-controlled Rh(<scp>iii</scp>)-catalyzed regiodivergent annulation towards fused and spiro benzimidazoles

Huang, Ying-Ti; Barve, Indrajeet J.; Huang, Yeou‐Lih; Dhole, Sandip; Chiu, Wei-Jung; Sun, Chung‐Ming

doi:10.1039/d2ob00906d

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Heterocycle Directed Spirocyclization1

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2023

2024

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Cited by 10 publications

(1 citation statement)

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“…In 2022, Huang et al reported a 2-arylbenzimidazole 172 directed spirocyclization using a Rh-catalyst in the presence of AgOAc and AcOH in acetonitrile medium at 100 °C (Scheme 43). 38 Several substituents on the maleimide as well as on the benzimidazole have been tested for the sake of generalization and 19–74% yields of the spirocycles 173 were isolated.…”

Section: Heterocycle Directed Spirocyclizationmentioning

confidence: 99%

Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Acharya,

Patra,

Maharana

et al. 2024

Org. Biomol. Chem.

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Section: Heterocycle Directed Spirocyclizationmentioning

confidence: 99%

Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Acharya,

Patra,

Maharana

et al. 2024

Org. Biomol. Chem.

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Rh(III)‐Catalyzed C−H Annulation and Spirolactonization of 2‐Aryl‐1H‐benzo[d]imidazoles with 4‐Hydroxy‐2‐alkynoates via C−H bond activation

Siva Sankaram,

Sahoo,

Madhu

et al. 2023

Asian J Org Chem

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Rh(III) catalyzed C−H bond annulation and spirolactonization of 2‐aryl‐1H‐benzo[d]imidazoles with 4‐hydroxy‐2‐alkynoates has been developed for the first time for the synthesis of a diverse range of 2’,2’‐dimethyl‐2’H‐spiro[benzo[4,5]imidazo[2,1‐a]isoindole and fused dimethylbenzo[4,5]imidazo[2,1‐a]furo[3,4‐c]isoquinoline derivatives. This method is a versatile and atom‐economical to produce polycyclic frameworks in a single‐step.

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Pd(II)‐Catalyzed Benzimidazole‐Assisted Annulation of 3‐(1H‐Benzo[d]imidazol‐2‐yl)‐2H‐chromen‐2‐one: Access to Imidazo[1,2‐a]chromeno[3,4‐c]pyridine

2023

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Palladium‐catalyzed [4+2] oxidative annulation of coumarin‐benzimidazoles with olefins for the synthesis of polycyclic aromatic hydrocarbons have been achieved. This synthetic protocol gives access to a wide range of structurally distinct imidazo[1,2‐a]chromeno[3,4‐c]pyridines in moderate to good yield with wide functional group tolerance. Further, photophysical properties of annulated scaffolds have been examined, which discloses their interesting solvatochromic emission behaviors.

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Substrate-controlled Rh(iii)-catalyzed regiodivergent annulation towards fused and spiro benzimidazoles

Abstract: Rh(III)-catalyzed cascade C-H activation and cyclization of 2-aryl benzimidazoles with maleimides for the synthesis of benzimidazole-fused isoquinolines and benzimidazole spiro isoindoles is reported. The switchable selectivity in the formation of...

Cited by 10 publications

References 26 publications

Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Recent advances in spirocyclization of maleimides via transition-metal catalyzed C–H activation

Rh(III)‐Catalyzed C−H Annulation and Spirolactonization of 2‐Aryl‐1H‐benzo[d]imidazoles with 4‐Hydroxy‐2‐alkynoates via C−H bond activation

Pd(II)‐Catalyzed Benzimidazole‐Assisted Annulation of 3‐(1H‐Benzo[d]imidazol‐2‐yl)‐2H‐chromen‐2‐one: Access to Imidazo[1,2‐a]chromeno[3,4‐c]pyridine

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