Iron-catalyzed radical Markovnikov hydrohalogenation and hydroazidation of alkenes

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Авг. 22, 2024

Abstract We herein report radical hydroazidation and hydrohalogenation of mono-, di- trisubstituted alkenes through iron catalysis. The alkene moiety that often occurs as a functionality in natural products is readily transformed into useful building blocks this approach. Commercially available tosylates α-halogenated esters are used trapping reagents combination with silanes reductants. reported Markovnikov hydroazidation, hydrobromination, hydrochlorination, hydroiodination occur under mild conditions. These hydrofunctionalizations valuable practical alternatives to ionic hydrohalogenations the corresponding mineral acids have be run harsher acidic conditions, which diminishes functional group tolerance. Good excellent diastereoselectivities can obtained for hydrofunctionalization cyclic alkenes.

Язык: Английский

The Progress of Reductive Coupling Reaction by Iron Catalysis

The Chemical Record, Год журнала: 2024, Номер unknown

Опубликована: Сен. 17, 2024

Abstract The transition metal catalyzed coupling reaction has revolutionized the strategies for forging carbon‐carbon bonds. In contrast to traditional cross‐coupling methods using pre‐prepared nucleophilic organometallic reagents, reductive reactions C−C bonds formation provide some advantages. Because both partners are reduced in final products a stoichiometric amount of reductant, this approach not only avoids need use sensitive species, but also provides an orthogonal and complementary access classical reaction. Notably, feature readily available fragments, promote good step economy, exhibit high functional group tolerance unique chemoselectivity, which have propelled their increasingly popular organic synthesis. recent years, due low price, minimal toxicity, environmentally benign character, iron‐catalyzed garnered significant attention from synthetic chemists pharmacologists, especially coupling. This review aims insightful overview advances reactions, illustrate possible mechanisms.

Язык: Английский

Dearomative Functionalization of Activated Quinolines: Transfer Hydrogenation/Cycloaddition Cascade to Construct α‐Tertiary Amines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(20), С. 4219 - 4227

Опубликована: Авг. 7, 2024

Abstract Cascade dearomative functionalization is a robust protocol to convert flat arenes into medicinally relevant three‐dimensional architectures with added new functionality. Herein, cycloaddition for synthesizing tetrahydroquinoline‐embedded α‐tertiary amine scaffolds has been developed employing quinolinium salts and sulfonyl azides under metal‐free conditions. An underexplored mechanistically distinct pathway unveiled, creating quaternary‐center‐bearing skeletons by an group migration during the transfer hydrogenation cascade reaction. This approach provided broad substrate scope of from plethora C3‐substituted azides. The post‐synthetic modifications have further diversified core interesting scaffolds. Preliminary mechanistic studies suggested involvement aziridine ring formation C‐3 position quinoline generate core.

Язык: Английский