Stable Meisenheimer Complexes as Powerful Photoreductants Readily Obtained from Aza‐Heteroaromatic Compounds DOI Creative Commons
Francesco Calogero,

Leonie Wilczek,

Emanuele Pinosa

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(44)

Опубликована: Июль 30, 2024

Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.

Язык: Английский

Difunctionalization Processes Enabled by Hexafluoroisopropanol DOI Creative Commons
Maciej Piejko, Joseph Moran, David Lebœuf

и другие.

ACS Organic & Inorganic Au, Год журнала: 2024, Номер 4(3), С. 287 - 300

Опубликована: Март 4, 2024

In the past 5 years, hexafluoroisopropanol (HFIP) has been used as a unique solvent or additive to enable challenging transformations through substrate activation and stabilization of reactive intermediates. this Review, we aim at describing difunctionalization processes which were unlocked when HFIP was involved. Specifically, focus on cyclizations additions alkenes, alkynes, epoxides, carbonyls that introduce wide range functional groups interest.

Язык: Английский

Процитировано

14
Photoredox-catalyzed three-component carbotrifluoromethylation of alkenes via radical–radical cross-coupling DOI
Lin Tang,

Ge Lv,

Taijun Wu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4708 - 4715

Опубликована: Янв. 1, 2024

A simple and practical visible light-driven photoredox-catalyzed three-component carbotrifluoromethylation of alkenes is revealed for the synthesis 1,4-bis(trifluoromethylated) compounds.

Язык: Английский

Процитировано

3
para-Selective C-H Functionalization of Anilines: A Review DOI
Fatemeh Doraghi,

Yasin Mohammadkhani Kalooei,

Negar Mehdi zadeh Darban

и другие.

Journal of Organometallic Chemistry, Год журнала: 2024, Номер 1019, С. 123313 - 123313

Опубликована: Авг. 16, 2024

Язык: Английский

Процитировано

3
Understanding the Regiodivergence between Hydroarylation and Trifluoromethylarylation of 1,3-Dienes Using Anilines in HFIP DOI Creative Commons
Carlos Corral Suarez, Israel Fernández, Ignacio Colomer

и другие.

JACS Au, Год журнала: 2024, Номер 4(5), С. 1744 - 1751

Опубликована: Май 10, 2024

Conjugated dienes (1,3-dienes) are versatile and valuable chemical feedstocks that can be used as two-carbon or four-carbon synthons with vast applications across the industry. However, main challenge for their productive incorporation in synthetic routes is chemo-, regio-, stereoselective functionalization. Herein, we introduce a unified strategy 1,2-hydroarylation 1,4-trifluoromethylarylation of 1,3-dienes using anilines hexafluoroisopropanol. DFT calculations point toward kinetically controlled process both transformations, particularly trifluoromethylarylation, to explain regiodivergent outcome. In addition, perform an extensive program functionalization diversification products obtained, including hydrogenation, oxidation, cyclizations, cross-coupling reactions, allows access library high-value species straightforward manner.

Язык: Английский

Процитировано

2
Stable Meisenheimer Complexes as Powerful Photoreductants Readily Obtained from Aza‐Heteroaromatic Compounds DOI Creative Commons
Francesco Calogero,

Leonie Wilczek,

Emanuele Pinosa

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(44)

Опубликована: Июль 30, 2024

Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.

Язык: Английский

Процитировано

2
Oxidative Aminotrifluoromethylation of 1,4-Naphthoquinone DOI
Lin Tang,

Fengjuan Jia,

Ruijun Yu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13117 - 13127

Опубликована: Сен. 3, 2024

A strategy for convenient and precise oxidative aminotrifluoromethylation of 1,4-naphthoquinone with the Togni reagent amines has been demonstrated via a radical process. This method allows efficient access preparation wide range CF

Язык: Английский

Процитировано

2
Stable Meisenheimer Complexes as Powerful Photoreductants Readily Obtained from Aza‐Heteroaromatic Compounds DOI Creative Commons
Francesco Calogero,

Leonie Wilczek,

Emanuele Pinosa

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(44)

Опубликована: Июль 30, 2024

Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.

Язык: Английский

Процитировано

0