Synthesis of α-amino nitriles through one-pot selective Ru-photocatalyzed oxidative cyanation of amines

Echevarría, Igor; Vaquero, M. Pilar; Quesada, Roberto; Espino, Gustavo

doi:10.1039/d0qi00580k

Cited by 13 publications

(8 citation statements)

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“… 20 We have also reported on a protocol to prepare α-amino nitriles through the Ru-photosensitized oxidative cyanation of amines. 21 …”

Section: Introductionmentioning

confidence: 99%

“…In a previous work, we have designed a family of new Ir(III) biscyclometalated complexes with β-carbolines as efficient photocatalysts for the one-pot oxidative thiocyanation of indolines, which produces the respective 3-thiocyanate indoles . We have also reported on a protocol to prepare α-amino nitriles through the Ru-photosensitized oxidative cyanation of amines …”

Section: Introductionmentioning

confidence: 99%

“…20 We have also reported on a protocol to prepare αamino nitriles through the Ru-photosensitized oxidative cyanation of amines. 21 In this work, we present the synthesis of new Ir(III) biscyclometalated complexes of general formula [Ir-(C^N) 2 (N^N′)]Cl, where C^N = 2-(2,4-difluorophenyl)pyridinate (dfppy) and N^N′ stands for different N,N-donor ligands containing the 2-(2′-pyridyl)benzimidazole scaffold. The ligand dfppy was chosen to obtain enhanced photoluminescent quantum yields and excited-state lifetimes, since this behavior is usually expected from the presence of electronwithdrawing groups, such as the −F atoms on the C^N ligands in this type of complexes.…”

Section: ■ Introductionmentioning

confidence: 99%

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Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2′-Pyridyl)benzimidazole Scaffold

et al. 2022

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Photoredox catalysis constitutes a very powerful tool in organic synthesis, due to its versatility, efficiency, and the mild conditions required by photoinduced transformations. In this paper, we present an efficient and selective photocatalytic procedure for the aerobic oxidative dehydrogenation of partially saturated N-heterocycles to afford the respective N-heteroarenes (indoles, quinolines, acridines, and quinoxalines). The protocol involves the use of new Ir(III) biscyclometalated photocatalysts of the general formula [Ir(C^N) 2 (N^N′)]Cl, where the C^N ligand is 2-(2,4-difluorophenyl)pyridinate, and N^N′ are different ligands based on the 2-(2′-pyridyl)benzimidazole scaffold. In-depth electrochemical and photophysical studies as well as DFT calculations have allowed us to establish structure–activity relationships, which provide insights for the rational design of efficient metal-based dyes in photocatalytic oxidation reactions. In addition, we have formulated a dual mechanism, mediated by the radical anion superoxide, for the above-mentioned transformations.

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“… 20 We have also reported on a protocol to prepare α-amino nitriles through the Ru-photosensitized oxidative cyanation of amines. 21 …”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2′-Pyridyl)benzimidazole Scaffold

et al. 2022

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“…They were able to synthesize the cyano derivative by utilizing TMSCN as the cyanating medium, and obtained the desired product in 74% yield. Espino and co-workers developed and characterized a variety of dicationic Ru(II) polypyridyl complexes with 2-(pyridyl)benzimidazole or its N-alkylated derivatives as the ancillary ligands (N^N) [43]. The prepared Ru(II) derivatives were found effi-cient in the synthesis of α-amino nitriles from a pot strategy.…”

Section: Photocatalyzed Cyanation Reactionsmentioning

confidence: 99%

“…Espino and co-workers developed and characterized a variety of dicationic Ru(II) polypyridyl complexes with 2-(pyridyl)benzimidazole or its N-alkylated derivatives as the ancillary ligands (N^N) [ 43 ]. The prepared Ru(II) derivatives were found efficient in the synthesis of α-amino nitriles from amines via a one-pot strategy.…”

Section: Reviewmentioning

confidence: 99%

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

Aneeja¹,

Afsina²,

Saranya³

et al. 2022

Beilstein J. Org. Chem.

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Highly‐Doped Lanthanide‐Based Nanocrystals with Cooperative Core‐Shell Upconversion Emission for Multicomponent One‐Pot Chemical Transformations

Wu,

Yeow

2023

Advanced Optical Materials

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In order to apply near infrared (NIR) light‐activated upconversion nanocrystals (UCNCs) in photochemistry, extremely bright luminescence is needed to excite the ultraviolet (UV)‐visible light absorbing photocatalyst/substrate. In this study, a multilayered UCNC consisting of a β‐NaYF4:Yb0.2, Tm0.005 core, heavily Yb3+‐doped β‐NaYbF4:Y0.09, Tm0.01 intermediate shell, and inert β‐NaYF4 outer shell is prepared. By compartmentalizing the sensitizer (Yb3+)‐activator (Tm3+) pair in the core and intermediate shell with different concentration ratios, a cooperative luminescence effect is discovered. Apart from core emission, energy harvesting followed by sequential energy transfer from a high density of neighboring Yb3+ to Tm3+ in the intermediate shell induces a large population of excited emitter ions. Furthermore, after back energy transfer from the core to intermediate shell, the energy is not quenched by intrinsic trap sites but is instead transferred to Tm3+, further boosting emission in the UV, blue, and NIR regions. The exceptionally bright UCNC is then used to drive NIR‐light‐activated one‐pot multicomponent reactions involving the upconversion energy transfer from UCNC to UV‐visible light absorbing photocatalyst/substrate, Lewis acid catalytic activity of the lanthanide ions (Y3+) on the surface, and photothermal property of the UCNC. The reactions studied include the deacetalization‐Knoevenagel condensation reaction, photooxidation‐cyanation reaction, and hydrodehalogenation‐cyanosilylation reaction.

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Synthesis of α-amino nitriles through one-pot selective Ru-photocatalyzed oxidative cyanation of amines

Abstract: Photocatalysis is an expanding tool to synthesize organic molecules in a very efficient and selective way, using mild and environmentally friendly conditions. Thus, the development of new photosensitizers and photocatalytic...

Cited by 13 publications

References 55 publications

Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2′-Pyridyl)benzimidazole Scaffold

Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2′-Pyridyl)benzimidazole Scaffold

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

Highly‐Doped Lanthanide‐Based Nanocrystals with Cooperative Core‐Shell Upconversion Emission for Multicomponent One‐Pot Chemical Transformations

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