Photocatalytic EnT-Mediated Aminophosphorylation of Alkenes Using Oxime Esters as Bifunctional Reagents

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 19, 2024

C–P bond formation has typically been achieved by a single-electron transfer process. Herein, novel class of oxime ester bifunctionalization reagents were first applied to the photocatalytic β-aminophosphorylation modular olefins. The bifunctional generate two distinct radical species (imine and phosphoryl radicals) that exhibit excellent regioselectivity. Subsequently, these radicals are attached olefins through single-step EnT catalytic process, establishing synthetic pathway. This protocol is characterized regioselectivity, broad functional group tolerance, mild reaction conditions, which would enrich diversity versatility facilitate diversity-oriented synthesis β-aminophosphorylated complex molecule scaffolds.

Язык: Английский

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Breakthrough in phosphonylation of alkyl radicals: Alternative access of alkyl phosphonates

Chem, Год журнала: 2023, Номер 9(10), С. 2735 - 2737

Опубликована: Окт. 1, 2023

Язык: Английский

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Deoxygenative Transformation of Alcohols via Phosphoranyl Radical from Exogenous Radical Addition

Angewandte Chemie, Год журнала: 2024, Номер 136(17)

Опубликована: Фев. 15, 2024

Abstract A general approach to the direct deoxygenative transformation of primary, secondary, and tertiary alcohols has been developed. It undergoes through phosphoranyl radical intermediates generated by addition exogenous iodine trivalent alkoxylphosphanes. Since these alkoxylphosphanes are readily in situ obtained from commercially available, inexpensive chlorodiphenylphosphine, a diverse range with various functional groups can be utilized proceed cross‐couplings alkenes or aryl iodides. The selective polyhydroxy substrates rapid synthesis complex organic molecules also demonstrated this method.

Язык: Английский

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Photochemical Phosphorus-Enabled Scaffold Remodeling of Carboxylic Acids

Опубликована: Май 9, 2024

The excitation of carbonyl compounds by light to generate radical intermediates is a distinctive mode molecular activation. These processes play important roles in organic synthesis, especially for the challenging formation carbon-carbon bonds that conventional two-electron chemical are unable achieve. This approach has historically been restricted ketones and aldehydes, carboxylic acids have overlooked due high energy requirements their low quantum efficiency. development robust general method direct acid derivatives holds significant promise advancing field chemistry. A successful activation strategy necessitates bathochromic shift absorbance profile, an increase triplet diradical lifetime, ease further functionalization. We present phosphorus-based through single-flask transformation into acyl phosphonates access synthetically useful diradicals under visible or near-ultraviolet irradiation. use phosphorus circumvents unproductive Norrish type I processes, promoting selectivity enables new hydrogen atom transfer (HAT) logic facilitates diverse reactivity. Employing this promotes efficient scaffold remodeling various annulation, contraction, expansion manifolds. HAT enabled easily accessed represents potential pharmaceuticals, materials science, environmental applications.

Язык: Английский

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Photocatalytic C(sp³)–P and C(sp²)–P Bond Formation via a Phosphorus Radical Cation

Organic Letters, Год журнала: 2024, Номер 26(42), С. 9056 - 9061

Опубликована: Окт. 14, 2024

A straightforward method for the phosphorylation of electron-deficient alkenes and aryl alkynes has been developed, leading to C(sp

Язык: Английский

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