Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7298 - 7303

Published: Oct. 3, 2023

An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones iodonium ylides has been developed. The novel strategy allows access to new class of structurally diverse tetrahydro-indolones with high efficiency broad substrate scope. In addition, this transformation represents the first example selective alkenyl C–H bond functionalization enaminones. Finally, potential applications are demonstrated through gram-scale reaction late-stage modification.

Language: Английский

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Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7214 - 7219

Published: Sept. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Language: Английский

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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2363 - 2369

Published: March 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Language: Английский

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Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5660 - 5666

Published: Jan. 1, 2023

Highly functionalized 3a,7a-dihydroxy hexahydro-4 H -indol-4-ones were efficiently synthesized via a Ru( iii )-catalyzed alkenyl C(sp 2 )–H bond functionalization/[3 + 2] annulation reaction between readily available enaminones and iodonium ylides.

Language: Английский

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Rh(iii)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

Chemical Communications, Journal Year: 2023, Volume and Issue: 60(4), P. 432 - 435

Published: Dec. 5, 2023

Highly functionalized benzodiazepine skeletons were efficiently synthesized via a Rh( iii )-catalyzed selective mono- and dual-C–H bond functionalization/cyclization reaction between readily available 1-aryl-5-aminopyrazoles iodonium ylides under.

Language: Английский

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Fe(OTf)₃-catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4298 - 4304

Published: Jan. 1, 2023

This method involves a cascade reaction utilizing 1 and enamines 2 as substrates, which occurred by refluxing mixture of the starting materials in toluene with catalyst Fe(OTf) 3 .

Language: Английский

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Synthesis of Hexabenzocoronene‐cored Graphdiyne Nanosheets through Dehydrogenative Coupling on Au(111) Surface

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 31, 2024

Abstract Thermally‐induced dehydrogenative coupling of polyphenylenes on metal surfaces is an important technique to synthesize ‐conjugated carbon nanostructures with atomic precision. However, this protocol has rarely been utilized fabricate structurally defined nanosheets composed sp‐ and sp 2 ‐hybridized atoms. Here, we present the synthesis butadiyne‐linked hexabenzocoronenes (HBCs) Au(111) as core‐expanded graphdiynes. The reaction started from hexa(4‐ethylphenyl)benzene, which undergoes dehydrogenation toward hexa(4‐vinylphenyl)benzene, followed by planarization hexabenzocoronene, between vinyl groups, further dehydrogenation. In addition butadiyne linkages, benzene groups were also found another type linker. sequences monitored scanning tunneling microscopy bond‐resolved non‐contact force microscopy, disclose structures intermediates final products. combination density functional theory simulations, key steps ethyl substituents linkers elucidated. This a new on‐surface graphdiynes unprecedented electronic properties.

Language: Английский

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Utilizing a copper foam electrode as the catalyst in Sonogashira C-H activation coupling reactions for the electro-oxidation synthesis of diphenylethyne derivatives

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1305, P. 137757 - 137757

Published: Feb. 8, 2024

Language: Английский

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Synthesis of Hexabenzocoronene‐Cored Graphdiyne Nanosheets through Dehydrogenative Coupling on Au(111) Surface

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 31, 2024

Abstract Thermally‐induced dehydrogenative coupling of polyphenylenes on metal surfaces is an important technique to synthesize ‐conjugated carbon nanostructures with atomic precision. However, this protocol has rarely been utilized fabricate structurally defined nanosheets composed sp‐ and sp 2 ‐hybridized atoms. Here, we present the synthesis butadiyne‐linked hexabenzocoronenes (HBCs) Au(111) as core‐expanded graphdiynes. The reaction started from hexa(4‐ethylphenyl)benzene, which undergoes dehydrogenation toward hexa(4‐vinylphenyl)benzene, followed by planarization hexabenzocoronene, between vinyl groups, further dehydrogenation. In addition butadiyne linkages, benzene groups were also found another type linker. sequences monitored scanning tunneling microscopy bond‐resolved non‐contact force microscopy, disclose structures intermediates final products. combination density functional theory simulations, key steps ethyl substituents linkers elucidated. This a new on‐surface graphdiynes unprecedented electronic properties.

Language: Английский

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Cascade [3 + 2]/[4 + 2] Cycloaddition of Enaminones with Vinylene Carbonate for the Synthesis of Functionalized Pyrrolo[2,1-a]isoquinoline Derivatives

Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9752 - 9758

Published: Nov. 6, 2024

We developed a protocol for the synthesis of functionalized pyrrolo[2,1-a]isoquinoline derivatives (PIQDs) 3 from enaminones 1 using vinylene carbonate 2. This strategy involved [3 + 2] and [4 cycloadditions via heating mixture substrates with 2 DCE at 60 °C, catalyzed by [Cp*RhCl2]2 oxidized Cu(OAc)2 AgSbF6 promoted NaOAc. As we increased reaction temperature to 110 °C under same conditions, synthesized PIQDs 4 through sequential C–H activation, alkene insertion, migratory C–N reductive elimination, β-O finally dehydration. result, series 3–4 were generated forming four bonds (2 C–C bonds) in single step. realizes linear molecules potential biological activity, specifically natural-like heterocycles (3–4). It expands application as C2 synthon construction pyrrole isoquinoline skeletons combinatorial parallel syntheses one-pot reactions.

Language: Английский

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