Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2752 - 2906

Published: Aug. 10, 2021

Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing plethora opportunities to synthetic organic chemists. However, performing photochemical transformation can be quite challenge because various issues related the delivery photons. These challenges barred widespread adoption steps industry. past decade, several technological innovations led more reproducible, selective, and scalable photoinduced reactions. Herein, we provide comprehensive overview these exciting advances, including flow chemistry, high-throughput experimentation, reactor design scale-up, combination photo- electro-chemistry.

Language: Английский

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Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2487 - 2649

Published: Nov. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Language: Английский

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Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(17), P. 9540 - 9685

Published: Jan. 1, 2021

Visible light-activated reactions continue to expand and diversify. The example shown here is a Birch reduction achieved by organophotoredox reagents.

Language: Английский

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Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 50(2), P. 766 - 897

Published: Dec. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Language: Английский

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Photoredox catalysis over semiconductors for light-driven hydrogen peroxide production

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(4), P. 1466 - 1494

Published: Jan. 1, 2021

This critical review presents recent advances in light-driven H₂O₂ production from the viewpoint of generation pathways.

Language: Английский

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Advanced catalytic ozonation for degradation of pharmaceutical pollutants―A review

Chemosphere, Journal Year: 2021, Volume and Issue: 289, P. 133208 - 133208

Published: Dec. 7, 2021

Language: Английский

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Advances in asymmetric organocatalysis over the last 10 years

Nature Communications, Journal Year: 2020, Volume and Issue: 11(1)

Published: July 29, 2020

Beyond esoteric interest, organocatalysis has now become one major pillar of asymmetric catalysis. Here, we discuss how new activation modes are conquering challenging stereoselective transformations and the recent integration with emerging photo- electrocatalysis, as well artificial intelligence. Organocatalysis a (asymmetric) authors trends in organocatalytic for other fields, such photoredox catalysis electrosynthesis.

Language: Английский

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Dual Metalation in a Two-Dimensional Covalent Organic Framework for Photocatalytic C–N Cross-Coupling Reactions

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(17), P. 7822 - 7833

Published: April 21, 2022

Covalent organic frameworks (COFs) are promising hosts in heterogeneous catalysis. Herein, we report a dual metalation strategy single two-dimensional-COF TpBpy for performing variety of C–N cross-coupling reactions. [Ir(ppy)2(CH3CN)2]PF6 [ppy = 2-phenylpyridine], containing two labile CH3CN groups, and NiCl2 used as iridium nickel-metal precursors, respectively, postsynthetic decoration the COF. Moving from traditional approach, focus on COF-backbone host visible-light-mediated nickel-catalyzed coupling The controlled recyclability without deactivation both catalytic centers unique with respect to previously reported strategies. We performed various photoluminescence, electrochemical, kinetic, Hammett correlation studies understand salient features catalyst reaction mechanism. Furthermore, theoretical calculations delineated feasibility electron transfer Ir center Ni inside confined pore metal anchoring within COF backbone prevented nickel-black formation. developed protocol enables selective reproducible diverse range amines (aryl, heteroaryl, alkyl), carbamides, sulfonamides electron-rich, neutral, poor (hetero) aryl iodides up 94% isolated yield. can also be gram scale. establish practical implementation this have applied synthetic late-stage diversification derivatives ibuprofen, naproxen, gemfibrozil, helional, amino acids. methodology could synthesize pharmacophore N,5-diphenyloxazol-2-amine Food Drug Administration-approved drugs, including flufenamic acid, flibanserin, tripelennamine.

Language: Английский

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Emerging concepts in photocatalytic organic synthesis

iScience, Journal Year: 2021, Volume and Issue: 24(3), P. 102209 - 102209

Published: Feb. 21, 2021

Visible light photocatalysis has become a powerful tool in organic synthesis that uses photons as traceless, sustainable reagents. Most of the activities field focus on development new reactions via common photoredox cycles, but recently number exciting concepts and strategies entered less charted territories. We survey approaches enable use longer wavelengths show wavelength intensity are import parameters tuning reactivity photocatalyst to control or change selectivity chemical reactions. In addition, we discuss recent efforts substitute strong reductants, such elemental lithium sodium, by technological advances field.

Language: Английский

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Carbon Dots as Nano-Organocatalysts for Synthetic Applications

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(15), P. 8090 - 8105

Published: June 30, 2020

Over the last decades, organic chemistry has taken a resolute step toward green catalytic synthesis. This tries to ensure efficient and sustainable base chemical production, while also safeguarding human health environment. To this end, development of novel, nontoxic, effective systems that are capable driving value-added transformations in environmentally benign solvents (e.g., water) is highly desirable. Moreover, these new catalysts need be metal-free, easy-to-prepare, potentially recyclable. Carbon dots, which relatively carbon-based nanoparticles, fulfill all requirements because their outstanding physicochemical features thus have emerged as promising nanocatalytic platforms. Perspective highlights recent advances synthesis carbon dots applications catalysis photocatalysis, with particular attention nonmetal-doped systems. Finally, forward-looking opportunities within field mentioned here.

Language: Английский

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