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

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(7), P. 4508 - 4523

Published: March 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.

Language: Английский

Synthesis of α/β-Aromatic Peroxy Thiols Mediated by Iodine Source DOI

Kaifa Zhang,

Changhong Liu,

Dilshat Abdukerem

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3049 - 3057

Published: Feb. 9, 2024

Peroxygenated compounds have wide applications in various fields, including chemistry, pharmaceutical medicine, and materials science. However, there is still a need for more efficient environmentally friendly synthesis methods such compounds. Herein, we investigated the two-step, one-pot, regioselective of α/β-aromatic peroxy thiols. We explored substrates solvents reaction identified optimal conditions. successfully obtained several thiols moderate to good yields via selective generation effective intermediates iodoalkyl peroxides at room temperature without metal catalysts.

Language: Английский

Citations

2

Iron(ΙΙΙ) Catalyzed Aerobic Cα–Cβ Cleavage of Allylic Alcohols DOI Creative Commons

Georgia G. Bagkavou,

Christos I. Stathakis

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: June 18, 2024

Abstract The regiospecific C α −C β cleavage of allylic alcohols under modified aerobic Mukaiyama hydration conditions is presented. new methodology can be regarded as an equivalent a two‐step process, typical the parent alcohol followed by 1,2‐diol cleavage. A broad scope substrates, both cyclic and acyclic, are applicable, thus introducing substantial structural modification to core, especially former type substrates. Mechanistic investigation reaction reveals importance nearby hydroxyl group for deviation from pathway.

Language: Английский

Citations

2

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

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(2), P. 110167 - 110167

Published: June 22, 2024

Language: Английский

Citations

2

Advances in radical peroxidation with hydroperoxides DOI Creative Commons
Oleg V. Bityukov,

Pavel Yu. Serdyuchenko,

Andrey S. Kirillov

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2959 - 3006

Published: Nov. 18, 2024

Organic peroxides have become sought-after functionalities, particularly following the multi-tone consumption in polymer production and success medicinal chemistry. The selective introduction of a peroxide fragment at different positions on target molecule is priority modern reaction design. pioneering Kharasch-Sosnovsky peroxidation became basic universal platform for development methods, with its great potential rapid generation complexity due to ability couple resulting free radicals wide range partners. This review discusses recent advances radical Kharasch-type functionalization organic molecules OOR including free-component couplings. discussion has been structured by type substrate peroxidation: C(sp

Language: Английский

Citations

2

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

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(7), P. 4508 - 4523

Published: March 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.

Language: Английский

Citations

9