Direct Oxidation of Csp<sup>3</sup>−H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

Lesieur, Mathieu; Battilocchio, Claudio; Labes, Ricardo; Jacq, Jérôme; Génicot, Christophe; Ley, Steven V.; Pasau, Patrick

doi:10.1002/chem.201805657

Cited by 19 publications

(22 citation statements)

References 52 publications

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“…Lesieur and co-workers developed a continuous flow platform for the in situ generation of TFDO gas via 1,1,1-trifluoroacetone mixing with an aqueous solution of NaHCO 3 and oxone in a sequential manner. 70 The tertiary and benzylic Csp 3 –H bonds were transformed to the desired C–O bonds in a fast, scalable, and safer fashion through a continuous-flow process. And the scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane.…”

Section: Traditional Oxidation Reactions In Continuous Flowmentioning

confidence: 99%

Continuous flow technology-a tool for safer oxidation chemistry

et al. 2022

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Section: Traditional Oxidation Reactions In Continuous Flowmentioning

confidence: 99%

Continuous flow technology-a tool for safer oxidation chemistry

et al. 2022

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“…The formation of TFDO was detected by 19 F NMR and 1 H NMR spectroscopy, after in-line phase separation of the organic phase with a liquid-liquid membrane separator (Zaiput), proving the yield to be higher in flow than batch (5% in flow, compared to 2% in batch). The method also proved scaleable, as exemplified by the production of 2.7 g 1-adamantanol from adamantane using two 20 mL reactors equipped with static mixer coils (96% yield, productivity 1.17 g h −1 ) [245].…”

Section: − O Bond Formationmentioning

confidence: 99%

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

2020

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C-H functionalization chemistry is one of the most vibrant research areas within synthetic organic chemistry. While most researchers focus on the development of small-scale batch-type transformations, more recently such transformations have been carried out in flow reactors to explore new chemical space, to boost reactivity or to enable scalability of this important reaction class. Herein, an up-to-date overview of C-H bond functionalization reactions carried out in continuous-flow microreactors is presented. A comprehensive overview of reactions which establish the formal conversion of a C-H bond into carbon-carbon or carbonheteroatom bonds is provided; this includes metal-assisted C-H bond cleavages, hydrogen atom transfer reactions and C-H bond functionalizations which involve an S E-type process to aromatic or olefinic systems. Particular focus is devoted to showcase the advantages of flow processing to enhance C-H bond functionalization chemistry. Consequently, it is our hope that this review will serve as a guide to inspire researchers to push the boundaries of C-H functionalization chemistry using flow technology.

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“…In 2018, Patrick and coworkers reported a new general TFDO-mediated Csp 3 -H oxidation method has been enabled in a fast, efficient and simple fashion through a continuous flow process. ( Patrick et al, 2018 ) Figure 1A . By using the in situ generation of TFDO gas in continuous flow platform, the Csp 3 -H oxidation was achieved exclusively at the more sterically hindered Csp 3 -H site in moderate to excellent yields in a panel of adamantane derivatives.…”

Section: C-h Oxidations For Natural Product Diversificationmentioning

confidence: 99%

Novel Strategies in C-H Oxidations for Natural Product Diversification—A Remote Functionalization Application Summary

et al. 2021

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Selectively activating the distal inactive C-H bond for functionalization is one of the on-going challenge in organic synthetic chemistry. In recent years, benefiting from the development of selective synthesis methods, novel methodologies not only make it possible to break non-traditional chemical bonds and attain more diversity in inactive sites, but also provide more possibilities for the diversification of complex natural products. Direct C-H bond functionalization approaches make it feasible to explore structure-activity relationship (SAR), generate metabolites and derivatives, and prepare biological probes. Among them, direct oxidation of inert C-H bonds is one of the most common methods for natural product diversification. In this review, we focus on the application of remote functionalization of inert C-H bonds for natural products derivatization, including the establishment of oxidation methods, the regulation of reaction sites, and the biological activities of derivatives. We highlight the challenges and opportunities of remote functionalization of inert C-H bonds for natural product diversification through selected and representative examples. We try to show that inert C-H bond oxidation, properly regulated and optimized, can be a powerful and efficient strategy in both synthetic and medicinal chemistry.

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Direct Oxidation of Csp³−H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

Cited by 19 publications

References 52 publications

Continuous flow technology-a tool for safer oxidation chemistry

Continuous flow technology-a tool for safer oxidation chemistry

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

Novel Strategies in C-H Oxidations for Natural Product Diversification—A Remote Functionalization Application Summary

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Direct Oxidation of Csp3−H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

Cited by 19 publications

References 52 publications

Continuous flow technology-a tool for safer oxidation chemistry

Continuous flow technology-a tool for safer oxidation chemistry

Pushing the boundaries of C–H bond functionalization chemistry using flow technology

Novel Strategies in C-H Oxidations for Natural Product Diversification—A Remote Functionalization Application Summary

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Product

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Direct Oxidation of Csp³−H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow