Continuous photocatalyzed aerobic oxidation of benzylic organotrifluoroborates to benzaldehydes under Taylor flow conditions

Roseau, Mélanie; Dhaouadi, Nesrine; Rolando, Christian; Chausset‐Boissarie, Laëtitia; Penhoat, Maël

doi:10.1007/s41981-019-00053-w

Cited by 10 publications

(4 citation statements)

References 30 publications

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“…The oxygen-mediated photooxidation of benzylic organotrifluoroborates in flow was reported by Wang et al (Scheme 183). 758 In a batch setup equipped with an oxygen balloon, the corresponding aldehyde was obtained in only 12% yield over 180 min. In contrast, when switching to a flow setup (FEP capillary 1.58 mm ID, 0.875 mL), irradiated with high-power UV-LED, the aldehyde was obtained in 82% NMR yield.…”

Section: Photodecarboxylations and -Carboxylationsmentioning

confidence: 99%

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

et al. 2021

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

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Section: Photodecarboxylations and -Carboxylationsmentioning

confidence: 99%

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

et al. 2021

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“…Photochemistry and electrochemistry have recently attracted a renewed and increasing interest from the organic chemistry community. [29,[81][82][83][84][85] Photochemistry and electrochemistry are efficiently combined with continuous flow processes, hence leading to much more robust, reproducible and scalable processes. Recent reports also feature these techniques for innovative P-H insertion reactions.…”

Section: Photo-and Electrochemically-driven Processesmentioning

confidence: 99%

Continuous Flow Organophosphorus Chemistry

2020

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Organophosphorus derivatives are widespread compounds that chemists find from the bench to the plant, with numerous daily life applications. Besides their common utility for a wide range of notorious reactions such as the Wittig and Horner‐Wadsworth‐Emmons olefinations, the Arbuzov reaction, the Staudinger reaction, the Mitsunobu reaction as well as ligands for a large variety of organometallic complexes, organophosphorus compounds have also found numerous applications as active pharmaceutical ingredients and agrochemicals. Some organophosphorus derivatives are also infamously known as Chemical Warfare Agents. Within the context of generalized adoption of new process technologies in the Chemistry Toolbox, this review intends to give an update on the most recent and significant advances in continuous flow organophosphorus chemistry. Selected examples in methodology, total synthesis and for the preparation of industrially relevant targets are discussed for illustrating the assets of flow chemistry.

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“…5 Later, Penhoat group realized continuous photocatalyzed aerobic oxidation of benzylic trifluoroborates to benzaldehydes, using UV irradiation and Ir-based photocatalyst to generate benzylic radical intermediates (Scheme 1c). 6 In spite of these achievements, 7 generally, from alkylborons to the carbonyl moieties, sequential oxidation processes are still required via the intermediate of alcohols. 8 This situation leaves ample space to develop more step-economical pathways that directly connect alkylborons and the carbonyl groups in a single vessel.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced oxidation of benzylic boronic esters to ketones/aldehydes via α-borylalkyl radicals

et al. 2023

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Continuous photocatalyzed aerobic oxidation of benzylic organotrifluoroborates to benzaldehydes under Taylor flow conditions

Cited by 10 publications

References 30 publications

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

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

Continuous Flow Organophosphorus Chemistry

Photoinduced oxidation of benzylic boronic esters to ketones/aldehydes via α-borylalkyl radicals

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