Continuous flow telescopic oxidation of alcohols via generation of chlorine and hypochlorite

Sharma, Yachita; Moolya, S.; Joshi, Ramesh A.; Kulkarni, Amol A.

doi:10.1039/c6re00225k

Cited by 13 publications

(6 citation statements)

References 12 publications

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“…Since the oxidation of primary alcohols to aldehydes using a flow method has been reported, − some of these conditions were examined using a batch method (Table S1). As a result, it was found that aerobic oxidation conditions with a Cu I /TEMPO catalyst system developed by Stahl et al gave the desired aldehyde in a satisfactory 81% isolated yield (Table S1, entry 6).…”

Section: Resultsmentioning

confidence: 99%

Continuous-Flow Synthesis of Cationic Lipid SST-01 via Safe and Scalable Aerobic Oxidation and Reductive Amination

Fujiwara

Ishitani²,

Kobayashi³

2020

Org. Process Res. Dev.

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The synthesis of the cationic lipid SST-01, a key component of Kyowa Kirin's siRNA−lipid nanoparticles, through a two-step homogeneous continuous-flow process is described. Safe and scalable aerobic oxidation with a catalytic Cu I /TEMPO system and diluted oxygen (5% O 2 in N 2 ) was utilized in the first step to provide a lipid aldehyde. Subsequent reductive amination of the first-step eluent with methylamine using tetramethylammonium triacetoxyborohydride provided the target SST-01 in an overall yield of 95%.

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Section: Resultsmentioning

confidence: 99%

Continuous-Flow Synthesis of Cationic Lipid SST-01 via Safe and Scalable Aerobic Oxidation and Reductive Amination

Fujiwara

Ishitani²,

Kobayashi³

2020

Org. Process Res. Dev.

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“…In 2017, the Kulkarni research group used af low microreactor to achieveatelescopic approach for selectiveo xidation of alcohols to aldehydes (Figure 35). [37] The approach generated toxic chlorine gas from manganese dioxide and hydrochloric acid and used it to obtain ah igh-concentration sodiumh ypochlorite solution.A tt he specific pH and in the presence of "TEMPO" (nitroxyl radical) catalyst, the latter oxidized eight alcohols to aldehydes in as electivem anner with high yields (80-99 %). The use of the flow methodw as crucial to ensure safety while workingw ith chlorine gas.…”

Section: Multi-step Synthesis and Telescoped Continuous-flow Processmentioning

confidence: 99%

Multi‐Step Continuous‐Flow Organic Synthesis: Opportunities and Challenges

Jiao

Nie

et al. 2021

Chemistry A European J

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Continuous‐flow multi‐step synthesis takes the advantages of microchannel flow chemistry and may transform the conventional multi‐step organic synthesis by using integrated synthetic systems. To realize the goal, however, innovative chemical methods and techniques are urgently required to meet the significant remaining challenges. In the past few years, by using green reactions, telescoped chemical design, and/or novel in‐line separation techniques, major and rapid advancement has been made in this direction. This minireview summarizes the most recent reports (2017–2020) on continuous‐flow synthesis of functional molecules. Notably, several complex active pharmaceutical ingredients (APIs) have been prepared by the continuous‐flow approach. Key technologies to the successes and remaining challenges are discussed. These results exemplified the feasibility of using modern continuous‐flow chemistry for complex synthetic targets, and bode well for the future development of integrated, automated artificial synthetic systems.

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“…TEMPO has also been utilised as a transfer catalyst for selective alcohol oxidation using in situ-generated sodium hypochlorite as a stoichiometric oxidising agent [ 322 ]. Chlorine was produced by adding hydrochloric acid to solid MnO 2 and the gas stream directed to react with a flow of aqueous sodium hydroxide to yield sodium hypochlorite.…”

Section: Reviewmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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Continuous flow telescopic oxidation of alcohols via generation of chlorine and hypochlorite

Abstract: A 3-step continuous flow oxidation of alcohols is demonstrated with continuous generation of chlorine as the first step followed by its use for the flow synthesis of high strength sodium hypochlorite.

Cited by 13 publications

References 12 publications

Continuous-Flow Synthesis of Cationic Lipid SST-01 via Safe and Scalable Aerobic Oxidation and Reductive Amination

Continuous-Flow Synthesis of Cationic Lipid SST-01 via Safe and Scalable Aerobic Oxidation and Reductive Amination

Multi‐Step Continuous‐Flow Organic Synthesis: Opportunities and Challenges

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

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