Efficient Radical‐Mediated Intermolecular α‐Alkylation Reactions of Carbonyl Compounds with Nonactivated Alkenes

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(12)

Опубликована: Апрель 27, 2024

Abstract Alkylation reactions are fundamental carbon‐carbon bond‐forming in synthetic organic chemistry. Among them, intermolecular α‐alkylation of carbonyl compounds with alkenes important because they more atom‐economical than the equivalent processes using alkyl halides. However, nonactivated such as 1‐hexene, which can allow use a wide range valuable substrates, have been considered to be very challenging for long time. In this review, radical‐mediated discussed. The examples grouped into three types reactions: peroxide‐mediated reactions, metal‐oxidant‐mediated and photoactivated reactions. Photoredox‐catalyzed alkylation under visible‐light irradiation discussed particularly promising recent hot topic. This review provides brief history new prospects on process α‐carbonyl radical species.

Язык: Английский

---

Photoinduced Efficient Catalytic α-Alkylation Reactions of Active Methylene and Methine Compounds with Nonactivated Alkenes

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(42), С. 23160 - 23166

Опубликована: Окт. 17, 2023

In catalytic α-alkylation reactions of carbonyl compounds, although SN2-type substitution enolates with alkyl halides are a conventional methodology, addition alkenes more desirable because their atom-economical character; however, nonactivated challenging. Here, we developed highly efficient active methylene and methine compounds such as 1-decene using an organophotocatalyst lithium thiophenoxide Lewis acid/Brønsted base/hydrogen atom transfer (HAT) multifunctional catalyst under blue-light irradiation. The reaction was also performed higher degree efficiency continuous-flow system to obtain the products in multigram scales. present enables practical be achieved.

Язык: Английский

---

Synthetic Applications of Photochemically Generated Radicals from Protic C(sp³)−H Bonds

ChemCatChem, Год журнала: 2023, Номер 15(22)

Опубликована: Окт. 12, 2023

Abstract The utilization of photo‐induced processes in C−H functionalization via radical pathways has emerged as a highly promising strategy for the preparation and modification complex organic compounds. While current methods generating carbon‐centred radicals from bonds primarily focus on hydridic to yield nucleophilic species, reactivity potential applications electrophilic derived protic remain largely unexplored. In this review, we aim shed light seminal findings regarding activation C(sp 3 )−H while also showcasing noteworthy examples formation process. Mechanistically diverse modes are discussed, unified by proton‐coupled electron transfer (PCET) concepts.

Язык: Английский

---

Photo-Induced Pyridylic C(sp³)–H Alkylation with Unactivated Alkenes Enabled by Hydrogen Atom Transfer/Lewis Acid Cocatalysis

ACS Catalysis, Год журнала: 2024, Номер 14(20), С. 15036 - 15042

Опубликована: Сен. 27, 2024

Язык: Английский

---