Palladium‐Catalyzed Stagewise Strain‐Release‐Driven C−C Activation of Bicyclo[1.1.1]pentanyl Alcohols DOI
Songjie Yu,

Yinan Ai,

Lingfei Hu

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(24)

Published: March 25, 2022

A palladium-catalyzed chemoselective coupling of readily available bicyclo[1.1.1]pentanyl alcohols (BCP-OH) with various halides is reported, which offers expedient approaches to a wide range cyclobutanone and β,γ-enone skeletons via single or double C-C activation. The chemistry shows broad substrate scope in terms both the BCP-OH including series natural product derivatives. Moreover, dependency reaction chemodivergence on base additive has been investigated through experimental density functional theory (DFT) studies, expected significantly enrich modes increase synthetic potential preparing more complex molecules.

Language: Английский

Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions DOI

Tongyao Zhou,

Jie Zeng, Yang Liu

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1375 - 1380

Published: Jan. 1, 2024

A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides was developed. This protocol allowed the formation δ,δ-diaryl ketones in presence a readily available organic photocatalyst.

Language: Английский

Citations

5
Nickel-Catalyzed Deaminative Alkyl–Alkyl Cross-Coupling of Katritzky Salts with Cyclopropanols: Merging C–N and C–C Bond Activation DOI
Xingjie Zhang,

Shilin Cui,

Shuxin Wei

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2114 - 2118

Published: March 4, 2024

Herein, we report a general and practical nickel-catalyzed deaminative alkylation of Katritzky salts with cyclopropyl alcohols via merging C–N C–C bond activation. This protocol enables the formation an alkyl–alkyl along generation versatile ketone functional group in single operation, thus providing convenient approach for accessing β-alkyl ketones. reaction is distinguished by its high tolerance, broad substrate scope, efficient late-stage derivatization complex bioactive molecules.

Language: Английский

Citations

5
Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate DOI
Yoshiya Sekiguchi,

Yan Ying Lee,

Naohiko Yoshikai

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(15), P. 5993 - 5997

Published: July 22, 2021

We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both branched acyclic is also applicable to cyclic carbonates, affording variety δ,ε-unsaturated ketones in moderate good yields. Mechanistic experiments are accord catalytic cycle involving decarboxylative oxidative addition carbonate Ni(0), alkoxide exchange cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), C–C reductive elimination.

Language: Английский

Citations

27
Cobalt-catalyzed atom-economical, diastereo- and enantioselective coupling of aldimines and cyclopropanols DOI

Zhikun Liang,

Qinglei Chong,

Fanke Meng

et al.

Science China Chemistry, Journal Year: 2021, Volume and Issue: 64(10), P. 1750 - 1755

Published: Aug. 30, 2021

Language: Английский

Citations

25
Palladium‐Catalyzed Stagewise Strain‐Release‐Driven C−C Activation of Bicyclo[1.1.1]pentanyl Alcohols DOI
Songjie Yu,

Yinan Ai,

Lingfei Hu

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(24)

Published: March 25, 2022

A palladium-catalyzed chemoselective coupling of readily available bicyclo[1.1.1]pentanyl alcohols (BCP-OH) with various halides is reported, which offers expedient approaches to a wide range cyclobutanone and β,γ-enone skeletons via single or double C-C activation. The chemistry shows broad substrate scope in terms both the BCP-OH including series natural product derivatives. Moreover, dependency reaction chemodivergence on base additive has been investigated through experimental density functional theory (DFT) studies, expected significantly enrich modes increase synthetic potential preparing more complex molecules.

Language: Английский

Citations

18