Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP)

Topics in Current Chemistry, Journal Year: 2025, Volume and Issue: 383(1)

Published: Jan. 18, 2025

Language: Английский

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Chemoselective Csp²‐H Radical Alkylation of Aryl Diazonium Salts with 1‐Iodo‐3‐Pentafluorosulfanylbicyclo[1,1,1]pentane (SF5‐BCP‐I)^†

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Comprehensive Summary The reaction site of aryl diazonium salt was restricted in the position moiety, due to intrinsic electrophilicity moiety. Herein, we described an unprecedented chemoselective alkylation Csp 2 ‐H salts with 1‐iodo‐3‐pentafluorosulfanylbicyclo[1,1,1]pentane (SF 5 ‐BCP‐I). This novel provided efficient access various SF ‐BCP substituted aromatics that might have great potential application drug discovery. Mechanistic experiments and theoretical studies revealed electrophilic radical resulted thermodynamic favorable addition on rather than moiety salt.

Language: Английский

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Photoredox/Copper Cooperatively Catalyzed Arylalkynylation of [1.1.1]Propellane

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

We present a sp2–sp3/sp3–sp bond formation reaction through three-component coupling strategy involving terminal alkynes, [1.1.1]propellane, and aryl thianthrenium salts that are prepared from arenes. The employs dual photo/copper catalysis system provides streamlined approach for assembling 1-alkynyl-3-aryl bicyclo[1.1.1]pentane derivatives with broad spectrum of functional group compatibility. Mechanistic studies suggest the generation radicals copper alkynide intermediates was involved.

Language: Английский

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The Application of Bicyclo[1.1.1]pentane as a Bioisostere of the Phenyl Ring in Pharmaceutical Chemistry

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 20, 2024

Abstract Bicyclo[1.1.1]pentane (BCP) is a bridging ring skeleton with three-dimensional structure. BCP bioisostere of the phenyl ring, tert-butyl group, and alkynes; it has excellent physical chemical properties compared so been widely considered by pharmaceutical chemistry. This short review examines related reports as changes in physicochemical biological activity after substitution. The solubility, clogP, metabolic toxicity drug are improved bioisosteres, but lower than ring. application research development will be further expanded to provide more possibilities for future innovation development. 1 Introduction 2 Replacement Phenyl Rings 3 Conclusion

Language: Английский

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Direct Diazoarylation of [1.1.1]Propellane with Arenediazonium Salts: A Modular Assembly of Arylated Diazo Bicyclo[1.1.1]pentanes

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

Published: Sept. 23, 2024

A mild and concise diazoarylation of [1.1.1]propellane is described, which provides a modular approach to arylated diazo bicyclopentanes (BCPs). This reaction proceeds smoothly under basic conditions without requiring other additives or catalysts. The substrate scope shows that various electron-withdrawing electron-donating groups are tolerated, the subsequent modifications provide novel avenue for assembling arylamino-BCP analogs.

Language: Английский

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