Asymmetric Photoredox Catalytic Minisci-Type Reactions of α-Bromide Amides

Organic Letters, Journal Year: 2025, Volume and Issue: 27(5), P. 1244 - 1249

Published: Jan. 23, 2025

An asymmetric photoredox catalytic Minisci-type reaction between α-bromide amides and imine-containing azaarenes has been successfully developed. This catalyst system employs a chiral phosphoric acid alongside 3DPAFIPN as photosensitizer. The produces diverse array of valuable amides, featuring azaarene-substituted tertiary carbon stereocenters at the β-position, in high yields (up to 85%) good excellent enantioselectivities >99% enantiomeric excess (ee)). Importantly, this work marks first example radical addition simple utilizing radicals functionalized with electron-withdrawing carbonyl groups, which are conventionally considered unfavorable for such transformations, especially an enantioselective manner.

Language: Английский

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Light Runs Across Iron Catalysts in Organic Transformations

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(66), P. 15052 - 15064

Published: July 2, 2020

Over the past decades, organometallic complexes with precious elements, such as ruthenium and iridium, are widely used visible-light photoredox catalysts. Recently, more based on earth-abundant inexpensive elements have been sensitizers in photochemistry. Although photoexcited state lifetimes of iron typically shorter than those traditional photosensitizers, utilization catalysts photochemistry has sprung up owing to their abundance, low price, nontoxicity, novel properties, including exhibiting ligand metal charge transfer states. This concept focuses recent advances light-driven catalysis organic transformations, iron/photoredox dual catalysis, light-induced generation active The prospect for future this field is also discussed.

Language: Английский

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General Access to C-Centered Radicals: Combining a Bioinspired Photocatalyst with Boronic Acids in Aqueous Media

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(21), P. 12727 - 12737

Published: Oct. 19, 2020

Carbon-centered radicals are indispensable building blocks for modern synthetic chemistry. In recent years, visible light photoredox catalysis has become a promising avenue to access C-centered from broad array of latent functional groups, including boronic acids. Herein, we present an aqueous protocol wherein water features starring role help transform aliphatic, aromatic, and heteroaromatic acids with bioinspired flavin photocatalyst. These used deliver diverse pool alkylated products, three pharmaceutically relevant compounds, via open-shell conjugate addition disparate Michael acceptors. The mechanism the reaction is investigated by computational studies, deuterium labeling, radical-trapping experiments, spectroscopic analysis.

Language: Английский

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Supramolecular Engineering and Self-Assembly Strategies in Photoredox Catalysis

ACS Catalysis, Journal Year: 2020, Volume and Issue: 11(2), P. 710 - 733

Published: Dec. 31, 2020

Visible-light-mediated photoredox catalysis has evolved as an efficient and mild alternative to conventional organic synthesis. Inspired by the elegance sophistication of natural photosynthetic machinery involving complex self-assembled systems, recently researchers have resorted implementation supramolecular chemistry in catalytic processes with objective achieving improved efficiency for known chemical reactions, well developing advanced methodologies inaccessible transformations. Supramolecular engineering offers ability customize existing properties traditional catalysts various self-assembly strategies expands their scope cutting-edge synthetic means noncovalent interactions different components. In this review, we summarize recent advances key achievements synthesis adopting techniques based on systems underline advantages mechanistic facets. Diverse directional interaction driven are thoroughly discussed. Furthermore, photocatalytic reactions within confined nanospaces (viz. micelles, vesicles, polymersomes, polymeric nanoparticles, gels etc.) summarized. Finally, a brief perspective encouraging future prospects challenges contemporary field is presented.

Language: Английский

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Enantioselective “organocatalysis in disguise” by the ligand sphere of chiral metal-templated complexes

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(17), P. 9715 - 9740

Published: Jan. 1, 2021

An overview about the principles, applications and perspectives on catalytic use of chiral metal-templated complexes that operate as “chiral organocatalysts in disguise” is presented.

Language: Английский

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