Illuminating Photoredox Catalysis

McAtee, Rory C.; McClain, Edward J.; Stephenson, Corey R. J.

doi:10.1016/j.trechm.2019.01.008

Cited by 386 publications

(245 citation statements)

References 97 publications

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“…Photochemistry has emerged in many cases as an alternative or complementary way to promote chemical reactions. For example, a recent review by Stephenson nicely discusses the complementarity between traditional (thermal) chemistry and photoredox processes in the fields of crosscoupling reactions and alkene functionalization [1]. For instance, in the first case, more stubborn substrates in thermal reactions (e.g., alkyl halides) can be efficiently employed under photoredox conditions, or limitations in oxidative additions or transmetalation steps can be overcome.…”

Section: Before the Flow: Traditional Versus Photochemical Methodsmentioning

confidence: 99%

Flow Photochemistry: Shine Some Light on Those Tubes!

Sambiagio

Noël

2020

Trends in Chemistry

296

223

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Continuous-flow chemistry has recently attracted significant interest from chemists in both academia and industry working in different disciplines and from different backgrounds. Flow methods are now being used in reaction discovery/methodology, in scale-up and production, and for rapid screening and optimization. Photochemical processes are currently an important research field in the scientific community and the recent exploitation of flow methods for these methodologies has made clear the advantages of flow chemistry and its importance in modern chemistry and technology worldwide. This review highlights the most important features of continuous-flow technology applied to photochemical processes and provides a general perspective on this rapidly evolving research field. Microflow Technology and Photochemistry: A Perfect MatchThe use of light to promote chemical reactions has been exploited since the 18th century, but only recently a resurgence has been observed in synthetic organic chemistry, in particular due to the development of visible-light photoredox catalysis [1-5]. All transformations involving light (e.g., Figure 1A-D) must consider, besides classical chemical parameters (i.e., reaction conditions), the photophysical aspects of the sensitizer (see Glossary)/photocatalyst (when used), and the reactor design. The latter, although often neglected by chemists, is a critical aspect for the outcome of the studied chemical transformation. This includes, for example, the size, shape, and material of the reaction vessel, the characteristics and positioning of the light source(s), and heat-transfer properties, particularly when high-intensity lamps are used [6,7]. The engineering and technological aspects of photochemical processes are often at the basis of the irreproducibility and non-scalability of such transformations.According to the Beer-Lambert law, light transmittance decreases exponentially with the distance from the light source ( Figure 1F). For a standard batch reactor (diameter at least in the centimeter range), light intensity decreases considerably from the flask walls to the middle of the reaction mixture, resulting in slow reactions and nonhomogeneous irradiation of the reaction mixture. Performing photochemical reactions in microchannels (ID < 1 mm) allows a higher and more homogeneous photon flux, resulting in shorter reaction times and consequently less side-product formation due to over-irradiation, often observed in batch [8,9]. Another advantage of microflow chemistry, correlated with the large surface:volume ratio, is improved heat and mass transfer, with the possibility to perform mass-transfer-limited multiphasic reactions efficiently [10]. Reactive chemicals and intermediates can be handled more safely in flow than in batch, as no accumulation of dangerous components occurs within the confined reactor volume due to the continuous nature of the process. Together, these result in often faster, safer, and higher-yielding reactions, with the possibility to perform reactions under condition...

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Section: Before the Flow: Traditional Versus Photochemical Methodsmentioning

confidence: 99%

Flow Photochemistry: Shine Some Light on Those Tubes!

Sambiagio

Noël

2020

Trends in Chemistry

296

223

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“…The photochemistry of transition metal complexes underpins a range of applications, including organic light-emitting diode (OLED) development, 1,2 solar energy conversion, [3][4][5][6] and photoredox catalysis. [7][8][9][10][11] The photocatalysts in these systems usually operate via pathways that involve excited state single-electron transfer (SET), and careful photophysical and photochemical studies have established factors that give rise to photocatalysts with long excited-state lifetimes and good long-term stability. [12][13][14][15] In terms of electronic structure, a large ligand eld splitting (or a d 10 conguration) is oen critical.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic basis for tuning iridium hydride photochemistry from H₂ evolution to hydride transfer hydrodechlorination

et al. 2020

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“…[1] Last decades witnessed great development in photocatalysis to improve the organic synthetic protocols in terms of efficiency and selectivity. [2] Photocatalysis grabs much attention of scientific community because of its wide applicability in many scientific fields ranging from materials to synthetic chemistry including medicinal chemistry. [3] Visible light mediated photoredox catalysis is becoming a bench top transformation for many researchers to make CÀ C, CÀ X (X-halo, hetero atom) bond formations, [4] CÀ H bond functionalizations, cycloadditions and many functional group transformations etc.…”

Section: Introductionmentioning

confidence: 99%

Lead‐halides Perovskite Visible Light Photoredox Catalysts for Organic Synthesis

Murugesh

Singh

2020

The Chemical Record

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Lead-halide perovskites has grabbed great attention in recent years due to its unique photophysical and electrical properties. It has open new window in organic solar cell application for commercial point. Research has extended its application further towards visible light photoredox catalysts for organic synthesis. Due to intrinsic redox properties, sharp absorption and emissions patterns makes lead-halide perovskites as promising photoredox catalyst. In the presence of light, perovskite absorbs light, generates electrons/holes, which can reduce or oxidize species at reactive centres of organic molecule, leads to organic transformation. Lead-halide perovskites are used as heterogeneous catalysts for small molecules activations like CO, CH 4 and NO, also suitable photocatalysts for organic bond formations, oxidations, reductions, polymerizations and dimerization transformations. Recent literatures have set another milestone for perovskite materials in organic synthesis. This review provides information on lead-halides perovskite in visible-light photoredox catalysis such as CÀ C, CÀ X (X-halo, hetero atom) bond formations CÀ H arylation.

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Illuminating Photoredox Catalysis

Cited by 386 publications

References 97 publications

Flow Photochemistry: Shine Some Light on Those Tubes!

Flow Photochemistry: Shine Some Light on Those Tubes!

Mechanistic basis for tuning iridium hydride photochemistry from H₂ evolution to hydride transfer hydrodechlorination

Lead‐halides Perovskite Visible Light Photoredox Catalysts for Organic Synthesis

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Illuminating Photoredox Catalysis

Cited by 386 publications

References 97 publications

Flow Photochemistry: Shine Some Light on Those Tubes!

Flow Photochemistry: Shine Some Light on Those Tubes!

Mechanistic basis for tuning iridium hydride photochemistry from H2 evolution to hydride transfer hydrodechlorination

Lead‐halides Perovskite Visible Light Photoredox Catalysts for Organic Synthesis

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Mechanistic basis for tuning iridium hydride photochemistry from H₂ evolution to hydride transfer hydrodechlorination