Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents DOI

Thangeswaran Ramar,

Murugaiah A. M. Subbaiah, Andivelu Ilangovan

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(7), С. 4508 - 4523

Опубликована: Март 15, 2022

The scope of chemoselective β-hydride elimination in the context arylation/alkenylation homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. preparative scope, which investigated with 48 examples, supported applicability this wide range substrates tolerating variety functional groups while delivering β-substituted enone and dienone derivatives 62-95% yields.

Язык: Английский

Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C–H/C–C bond activation DOI
Yixin Cui, Dachang Bai, Bingxian Liu

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(100), С. 15631 - 15634

Опубликована: Янв. 1, 2020

Cyclobutenones were used as an acylating reagent in rhodium(iii)-catalyzed C–H acylation of heteroarenes through C–C cleavage.

Язык: Английский

Процитировано

17

Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer DOI
Qinghong Zhang, Qiao Zhao, Xiaodi Wu

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер 36(2), С. 110167 - 110167

Опубликована: Июнь 22, 2024

Язык: Английский

Процитировано

2

Hydroxy Group-Enabled Regio- and Stereoselective Hydroalkylation of Alkynyl Cyclobutanol via Palladium-Catalyzed C–C Bond Activation of Cyclopropanol: A One-Step Access to Vinyl Cyclobutanols DOI
Lamphiza O. Najiar, Bedadyuti Vedvyas Pati, Gopal Krushna Das Adhikari

и другие.

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6314 - 6319

Опубликована: Июль 22, 2024

The regio-/stereoselective synthesis of vinyl cyclobutanols from alkynyl is demonstrated. Here, selective C-C bond activation the cyclopropyl alcohol ring has been achieved in presence cyclobutanol ring. KIE experiments indicated noninvolvement O-H oxidative addition step rate-determining step. Further, applicability these for 1,4-diketones and 1,6-diketone

Язык: Английский

Процитировано

2

Nickel-Catalyzed Arylation/Alkenylation of tert-Cyclobutanols with Aryl/Alkenyl Triflates via a CC Bond Cleavage DOI
Zhen Wang, Yuanyuan Hu,

Hongwei Jin

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 86(1), С. 466 - 474

Опубликована: Ноя. 30, 2020

Herein, we first present a nickel-catalyzed arylation and alkenylation of tert-cyclobutanols with aryl/alkenyl triflates via C–C bond cleavage. An array γ-substituted ketones was obtained in moderate-to-good yields, thus featuring earth-abundant nickel catalysis, broad substrate scope, simple reaction conditions. Preliminary mechanistic experiments indicated that β-carbon elimination pathways might be involved the catalytic cycle.

Язык: Английский

Процитировано

14

Orchestrating a β-Hydride Elimination Pathway in Palladium(II)-Catalyzed Arylation/Alkenylation of Cyclopropanols Using Organoboron Reagents DOI

Thangeswaran Ramar,

Murugaiah A. M. Subbaiah, Andivelu Ilangovan

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(7), С. 4508 - 4523

Опубликована: Март 15, 2022

The scope of chemoselective β-hydride elimination in the context arylation/alkenylation homoenolates from cyclopropanol precursors using organoboronic reagents as transmetalation coupling partners was examined. reaction optimization paradigm revealed a simple ligand-free Pd(II) catalytic system to be most efficient under open air conditions. preparative scope, which investigated with 48 examples, supported applicability this wide range substrates tolerating variety functional groups while delivering β-substituted enone and dienone derivatives 62-95% yields.

Язык: Английский

Процитировано

9