Light‐Driven Synthesis and Functionalization of Bicycloalkanes, Cubanes and Related Bioisosteres

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(14)

Published: Jan. 5, 2024

Abstract Bicycloalkanes, cubanes and their structural analogues have emerged as bioisosteres of (hetero)arenes. To meet increasing demand, the chemical community has developed a plethora novel synthetic methods. In this review, we assess progress made in field light‐driven construction functionalization such relevant molecules. We focused on diverse targets, well reaction processes giving access to: (i) [1.1.1]‐bicyclopentanes (BCPs); (ii) [2.2.1]‐bicyclohexanes (BCHs); (iii) [3.1.1]‐bicycloheptanes (BCHeps); (iv) cubanes; other structurally related scaffolds. Finally, future perspectives dealing with identification manifolds to new functionalized bioisosteric units are discussed.

Language: Английский

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Photocatalyzed radical multicomponent alkylacylation of [1.1.1]propellane to synthesize 1,3-disubstituted BCP ketones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4616 - 4622

Published: Jan. 1, 2023

An efficient and general photocatalytic three-component intermolecular alkylacylation of [1.1.1]propellane to synthezise 1,3-disubstituted BCP ketones has been achieved.

Language: Английский

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Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 661 - 671

Published: March 27, 2024

Herein, we report a visible-light-mediated palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines, affording unsaturated γ- ε-amino acid derivatives diverse structures. In this methodology, the compound readily transforms into hybrid α-ester alkylpalladium radical release dinitrogen. The intermediate selectively adds to double bond 1,3-diene allene, followed by allylpalladium path selective allylic substitution amine substrate, thereby leading single derivative. This approach proceeds under mild simple reaction conditions shows high functional group tolerance, especially in incorporation various bioactive molecules. studies on scale-up reactions derivatizations highlight practical utility multicomponent protocol.

Language: Английский

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Synthesis of Acyl Cyclopentaquinolinones through Simultaneous Construction of the Heterocyclic Scaffold and Introduction of the Acyl Group

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6292 - 6305

Published: April 16, 2024

Presented herein is an effective and concise synthesis of acyl cyclopentaquinolinone derivatives via the cascade reactions N-(o-ethynylaryl)acrylamides with α-diazo carbonyl compounds. The formation product involves a visible light-induced radical from compound followed by its addition onto acrylamide moiety to trigger double annulation, single-electron oxidation, β-elimination. To our knowledge, this first example in which scaffold was constructed along introduction group under light irradiation conditions. Compared literature methods for similar purpose, newly developed protocol has advantages such as readily accessible substrates, mild reaction conditions, valuable products, synthetic procedure, high sustainability. With all these merits, method expected find wide applications construction related heterocyclic skeletons.

Language: Английский

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Photocatalytic Diheteroarylation of [1.1.1]Propellane for the Construction of 1,3-Diheteroaryl Bicyclo[1.1.1]pentanes

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

Herein, we report a visible light-induced diheteroarylation reaction of [1.1.1]propellane to synthesize 1,3-diheteroaryl bicyclo[1.1.1]pentanes (BCPs). In this approach, heteroaryl radicals are generated from halides via photocatalysis and subsequently added [1.1.1]propellane. The

Language: Английский

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