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2024 | OriginalPaper | Buchkapitel

Sicherer Umgang mit gefährlichen Chemikalien im Durchfluss

verfasst von : Md Taifur Rahman, Thomas Wirth

Erschienen in: Flow-Chemie für die Synthese von Heterocyclen

Verlag: Springer International Publishing

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Zusammenfassung

Die Durchflusschemie hat sich im Laufe des letzten Jahrzehnts zu einem hervorragenden Werkzeugkasten für anspruchsvolle chemische Umwandlungen entwickelt. Hochexotherme und kinetisch schnelle Reaktionen sind selbst im kleinen Maßstab schwierig zu handhaben, während jede Hochskalierung erhebliche Risiken birgt, wenn herkömmliche Reaktoren in Betracht gezogen werden. Die Durchflusschemie ermöglicht eine exquisite Kontrolle über Mischsequenzen, Reaktionszeit und Abschreckung, die letztendlich den Weg für die Feinabstimmung der chemischen Reaktivität in ,Raum und Zeit‘ ebnet. Dieses Kapitel beschreibt die jüngsten Fortschritte der Durchflusschemie bei der Kontrolle und sogar Entdeckung neuer Reaktivitäten von hochgefährlichen chemischen Arten und instabilen Zwischenprodukten. Dieses Kapitel fasst faszinierende aktuelle Beispiele zusammen, die die Kraft der Durchflusschemie demonstrieren, um allgemein bekannte kryogene Reaktionen bei oder nahe Raumtemperatur, sicheres Handling und In-situ-Produktion von gefährlichen oder giftigen Reagenzien für chemische Umwandlungen durchzuführen, die in herkömmlichen Reaktoren allgemein als unsicher gelten.

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Literatur
1.
2.
Zurück zum Zitat Wirth T (2017) Novel organic synthesis through ultrafast chemistry. Angew Chem Int Ed 56:682–684CrossRef Wirth T (2017) Novel organic synthesis through ultrafast chemistry. Angew Chem Int Ed 56:682–684CrossRef
3.
Zurück zum Zitat Usutani H, Tomida Y, Nagaki A et al (2007) Generation and reactions of o-bromophenyllithium without benzyne formation using a microreader. J Am Chem Soc 129:3046–3047PubMedCrossRef Usutani H, Tomida Y, Nagaki A et al (2007) Generation and reactions of o-bromophenyllithium without benzyne formation using a microreader. J Am Chem Soc 129:3046–3047PubMedCrossRef
4.
Zurück zum Zitat Nagaki A, Ichinari D, Yoshida JI (2014) Three-component coupling based on flash chemistry. Carbolithiation of benzyne with functionalized aryllithiums followed by reactions with electrophiles. J Am Chem Soc 136:12245–12248PubMedCrossRef Nagaki A, Ichinari D, Yoshida JI (2014) Three-component coupling based on flash chemistry. Carbolithiation of benzyne with functionalized aryllithiums followed by reactions with electrophiles. J Am Chem Soc 136:12245–12248PubMedCrossRef
5.
Zurück zum Zitat Nagaki A, Kim H, Yoshida J (2009) Nitro-substituted aryl lithium compounds in microreactor synthesis: switch between kinetic and thermodynamic control. Angew Chem Int Ed 48:8063–8065CrossRef Nagaki A, Kim H, Yoshida J (2009) Nitro-substituted aryl lithium compounds in microreactor synthesis: switch between kinetic and thermodynamic control. Angew Chem Int Ed 48:8063–8065CrossRef
6.
Zurück zum Zitat Kim H, Min K-I, Inoue K et al (2016) Submillisecond organic synthesis: outpacing Fries rearrangement through microfluidic rapid mixing. Science 352:691–694PubMedCrossRef Kim H, Min K-I, Inoue K et al (2016) Submillisecond organic synthesis: outpacing Fries rearrangement through microfluidic rapid mixing. Science 352:691–694PubMedCrossRef
7.
Zurück zum Zitat Kim H, Inoue K, Yoshida J (2017) Harnessing [1,4], [1,5], and [1,6] anionic Fries-type rearrangements by reaction-time control in flow. Angew Chem Int Ed 56:7863–7866CrossRef Kim H, Inoue K, Yoshida J (2017) Harnessing [1,4], [1,5], and [1,6] anionic Fries-type rearrangements by reaction-time control in flow. Angew Chem Int Ed 56:7863–7866CrossRef
8.
Zurück zum Zitat Kim H, Nagaki A, Yoshida J (2011) A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds. Nat Commun 2:264PubMedCrossRef Kim H, Nagaki A, Yoshida J (2011) A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds. Nat Commun 2:264PubMedCrossRef
9.
Zurück zum Zitat Nagaki A, Kenmoku A, Moriwaki Y et al (2010) Cross-coupling in a flow microreactor: space integration of lithiation and Murahashi coupling. Angew Chem Int Ed 49:7543–7547CrossRef Nagaki A, Kenmoku A, Moriwaki Y et al (2010) Cross-coupling in a flow microreactor: space integration of lithiation and Murahashi coupling. Angew Chem Int Ed 49:7543–7547CrossRef
10.
Zurück zum Zitat Shu W, Pellegatti L, Oberli MA, Buchwald SL (2011) Continuous-flow synthesis of biaryls enabled by multistep solid-handling in a lithiation/borylation/Suzuki-Miyaura cross-coupling sequence. Angew Chem Int Ed 50:10665–10669CrossRef Shu W, Pellegatti L, Oberli MA, Buchwald SL (2011) Continuous-flow synthesis of biaryls enabled by multistep solid-handling in a lithiation/borylation/Suzuki-Miyaura cross-coupling sequence. Angew Chem Int Ed 50:10665–10669CrossRef
11.
Zurück zum Zitat Shu W, Buchwald SL (2012) Enantioselective β-arylation of ketones enabled by lithiation/borylation/1,4-addition sequence under flow conditions. Angew Chem Int Ed 51:5355–5358CrossRef Shu W, Buchwald SL (2012) Enantioselective β-arylation of ketones enabled by lithiation/borylation/1,4-addition sequence under flow conditions. Angew Chem Int Ed 51:5355–5358CrossRef
12.
Zurück zum Zitat Nagaki A, Moriwaki Y, Yoshida J (2012) Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki–Miyaura coupling without intentionally added base. Chem Commun 48:11211–11213CrossRef Nagaki A, Moriwaki Y, Yoshida J (2012) Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki–Miyaura coupling without intentionally added base. Chem Commun 48:11211–11213CrossRef
13.
Zurück zum Zitat Tomida Y, Nagaki A, Yoshida J (2011) Asymmetric carbolithiation of conjugated enynes: a flow microreactor enables the use of configurationally unstable intermediates before they epimerize. J Am Chem Soc 133:3744–3747PubMedCrossRef Tomida Y, Nagaki A, Yoshida J (2011) Asymmetric carbolithiation of conjugated enynes: a flow microreactor enables the use of configurationally unstable intermediates before they epimerize. J Am Chem Soc 133:3744–3747PubMedCrossRef
14.
Zurück zum Zitat Nagaki A, Matsuo C, Kim S et al (2012) Lithiation of 1,2-dichloroethene in flow microreactors: versatile synthesis of alkenes and alkynes by precise residence-time control. Angew Chem Int Ed 51:3245–3248CrossRef Nagaki A, Matsuo C, Kim S et al (2012) Lithiation of 1,2-dichloroethene in flow microreactors: versatile synthesis of alkenes and alkynes by precise residence-time control. Angew Chem Int Ed 51:3245–3248CrossRef
15.
Zurück zum Zitat Nagaki A, Takahashi Y, Yoshida J (2014) Extremely fast gas/liquid reactions in flow microreactors: carboxylation of short-lived organolithiums. Chem Eur J 20:7931–7934PubMedCrossRef Nagaki A, Takahashi Y, Yoshida J (2014) Extremely fast gas/liquid reactions in flow microreactors: carboxylation of short-lived organolithiums. Chem Eur J 20:7931–7934PubMedCrossRef
16.
Zurück zum Zitat Pieber B, Glasnov T, Kappe CO (2014) Flash carboxylation: fast lithiation–carboxylation sequence at room temperature in continuous flow. RSC Adv 4:13430–13433CrossRef Pieber B, Glasnov T, Kappe CO (2014) Flash carboxylation: fast lithiation–carboxylation sequence at room temperature in continuous flow. RSC Adv 4:13430–13433CrossRef
17.
Zurück zum Zitat Kupracz L, Kirschning A (2013) Multiple organolithium generation in the continuous flow synthesis of amitriptyline. Adv Synth Catal 355:3375–3380CrossRef Kupracz L, Kirschning A (2013) Multiple organolithium generation in the continuous flow synthesis of amitriptyline. Adv Synth Catal 355:3375–3380CrossRef
18.
Zurück zum Zitat Wu J, Yang X, He Z et al (2014) Continuous flow synthesis of ketones from carbon dioxide and organolithium or grignard reagents. Angew Chem Int Ed 53:8416–8420CrossRef Wu J, Yang X, He Z et al (2014) Continuous flow synthesis of ketones from carbon dioxide and organolithium or grignard reagents. Angew Chem Int Ed 53:8416–8420CrossRef
19.
Zurück zum Zitat Gross TD, Chou S, Bonneville D et al (2008) Chemical development of NBI-75043. Use of a flow reactor to circumvent a batch-limited metal-halogen exchange reaction. Org Process Res Dev 12:929–939CrossRef Gross TD, Chou S, Bonneville D et al (2008) Chemical development of NBI-75043. Use of a flow reactor to circumvent a batch-limited metal-halogen exchange reaction. Org Process Res Dev 12:929–939CrossRef
20.
Zurück zum Zitat Wakami H, Yoshida JI (2005) Grignard exchange reaction using a microflow system: from bench to pilot plant. Org Process Res Dev 9:787–791CrossRef Wakami H, Yoshida JI (2005) Grignard exchange reaction using a microflow system: from bench to pilot plant. Org Process Res Dev 9:787–791CrossRef
21.
Zurück zum Zitat Riva E, Gagliardi S, Martinelli M et al (2010) Reaction of Grignard reagents with carbonyl compounds under continuous flow conditions. Tetrahedron 66:3242–3247CrossRef Riva E, Gagliardi S, Martinelli M et al (2010) Reaction of Grignard reagents with carbonyl compounds under continuous flow conditions. Tetrahedron 66:3242–3247CrossRef
22.
Zurück zum Zitat Deng Q, Shen R, Ding R, Zhang L (2014) Generation of ethynyl-Grignard reagent in a falling film microreactor: an expeditious flow synthesis of propargylic alcohols and analogues. Adv Synth Catal 356:2931–2936CrossRef Deng Q, Shen R, Ding R, Zhang L (2014) Generation of ethynyl-Grignard reagent in a falling film microreactor: an expeditious flow synthesis of propargylic alcohols and analogues. Adv Synth Catal 356:2931–2936CrossRef
23.
Zurück zum Zitat Kawaguchi T, Miyata H, Ataka K et al (2005) Room-temperature Swern oxidations by using a microscale flow system. Angew Chem Int Ed 44:2413–2416CrossRef Kawaguchi T, Miyata H, Ataka K et al (2005) Room-temperature Swern oxidations by using a microscale flow system. Angew Chem Int Ed 44:2413–2416CrossRef
24.
Zurück zum Zitat Van Der Linden JJM, Hilberink PW, Kronenburg CMP, Kemperman GJ (2008) Investigation of the moffatt-swern oxidation in a continuous flow microreactor system. Org Process Res Dev 12:911–920CrossRef Van Der Linden JJM, Hilberink PW, Kronenburg CMP, Kemperman GJ (2008) Investigation of the moffatt-swern oxidation in a continuous flow microreactor system. Org Process Res Dev 12:911–920CrossRef
25.
Zurück zum Zitat Pelleter J, Renaud F (2009) Facile, fast and safe process development of nitration and bromination reactions using continuous flow reactors. Org Process Res Dev 13:698–705CrossRef Pelleter J, Renaud F (2009) Facile, fast and safe process development of nitration and bromination reactions using continuous flow reactors. Org Process Res Dev 13:698–705CrossRef
26.
Zurück zum Zitat Brocklehurst CE, Lehmann H, La Vecchia L (2011) Nitration chemistry in continuous flow using fuming nitric acid in a commercially available flow reactor. Org Process Res Dev 15:1447–1453CrossRef Brocklehurst CE, Lehmann H, La Vecchia L (2011) Nitration chemistry in continuous flow using fuming nitric acid in a commercially available flow reactor. Org Process Res Dev 15:1447–1453CrossRef
27.
Zurück zum Zitat Gage JR, Guo X, Tao J, Zheng C (2012) High output continuous nitration. Org Process Res Dev 16:930−933CrossRef Gage JR, Guo X, Tao J, Zheng C (2012) High output continuous nitration. Org Process Res Dev 16:930−933CrossRef
28.
Zurück zum Zitat Schwalbe T, Autze V, Hohmann M, Stirner W (2004) Novel innovation systems for a cellular approach to continuous process chemistry from discovery to market. Org Proc Res Dev 8:440–454CrossRef Schwalbe T, Autze V, Hohmann M, Stirner W (2004) Novel innovation systems for a cellular approach to continuous process chemistry from discovery to market. Org Proc Res Dev 8:440–454CrossRef
29.
Zurück zum Zitat Müller STR, Murat A, Maillos D et al (2015) Rapid generation and safe use of carbenes enabled by a novel flow protocol with in-line IR spectroscopy. Chem Eur J 21:7016–7020PubMedCrossRef Müller STR, Murat A, Maillos D et al (2015) Rapid generation and safe use of carbenes enabled by a novel flow protocol with in-line IR spectroscopy. Chem Eur J 21:7016–7020PubMedCrossRef
30.
Zurück zum Zitat Müller STR, Hokamp T, Ehrmann S et al (2016) Ethyl lithiodiazoacetate: extremely unstable intermediate handled efficiently in flow. Chem Eur J 22:11940–11942PubMedCrossRef Müller STR, Hokamp T, Ehrmann S et al (2016) Ethyl lithiodiazoacetate: extremely unstable intermediate handled efficiently in flow. Chem Eur J 22:11940–11942PubMedCrossRef
31.
Zurück zum Zitat Müller STR, Murat A, Hellier P, Wirth T (2016) Toward a large-scale approach to Milnacipran analogues using diazo compounds in flow chemistry. Org Process Res Dev 20:495–502CrossRef Müller STR, Murat A, Hellier P, Wirth T (2016) Toward a large-scale approach to Milnacipran analogues using diazo compounds in flow chemistry. Org Process Res Dev 20:495–502CrossRef
32.
Zurück zum Zitat Deadman BJ, Collins SG, Maguire AR (2015) Taming hazardous chemistry in flow: the continuous processing of diazo and diazonium compounds. Chem Eur J 21:2298–2308PubMedCrossRef Deadman BJ, Collins SG, Maguire AR (2015) Taming hazardous chemistry in flow: the continuous processing of diazo and diazonium compounds. Chem Eur J 21:2298–2308PubMedCrossRef
33.
Zurück zum Zitat Mastronardi F, Gutmann B, Oliver Kappe C (2013) Continuous flow generation and reactions of anhydrous diazomethane using a teflon AF-2400 tube-in-tube reactor. Org Lett 15:5590–5593PubMedCrossRef Mastronardi F, Gutmann B, Oliver Kappe C (2013) Continuous flow generation and reactions of anhydrous diazomethane using a teflon AF-2400 tube-in-tube reactor. Org Lett 15:5590–5593PubMedCrossRef
34.
Zurück zum Zitat Maurya RA, Park CP, Lee JH, Kim DP (2011) Continuous in situ generation, separation, and reaction of diazomethane in a dual-channel microreactor. Angew Chem Int Ed 50:5952–5955CrossRef Maurya RA, Park CP, Lee JH, Kim DP (2011) Continuous in situ generation, separation, and reaction of diazomethane in a dual-channel microreactor. Angew Chem Int Ed 50:5952–5955CrossRef
35.
Zurück zum Zitat Bartrum HE, Blakemore DC, Moody CJ, Hayes CJ (2010) Synthesis of β-keto esters in-flow and rapid access to substituted pyrimidines. J Org Chem 75:8674–8676PubMedCrossRef Bartrum HE, Blakemore DC, Moody CJ, Hayes CJ (2010) Synthesis of β-keto esters in-flow and rapid access to substituted pyrimidines. J Org Chem 75:8674–8676PubMedCrossRef
36.
Zurück zum Zitat Zhang X, Stefanick S, Villani FJ (2004) Application of microreactor technology in process development. Org Process Res Dev 8:455–460CrossRef Zhang X, Stefanick S, Villani FJ (2004) Application of microreactor technology in process development. Org Process Res Dev 8:455–460CrossRef
37.
Zurück zum Zitat Fuse S, Tanabe N, Takahashi T (2011) Continuous in situ generation and reaction of phosgene in a microflow system. Chem Commun 47:12661–12663CrossRef Fuse S, Tanabe N, Takahashi T (2011) Continuous in situ generation and reaction of phosgene in a microflow system. Chem Commun 47:12661–12663CrossRef
38.
Zurück zum Zitat Hamano M, Nagy KD, Jensen KF (2012) Continuous flow metal-free oxidation of picolines using air. Chem Commun 48:2086–2088CrossRef Hamano M, Nagy KD, Jensen KF (2012) Continuous flow metal-free oxidation of picolines using air. Chem Commun 48:2086–2088CrossRef
39.
Zurück zum Zitat He Z, Jamison TF (2014) Continuous-flow synthesis of functionalized phenols by aerobic oxidation of grignard reagents. Angew Chem Int Ed 53:3353–3357CrossRef He Z, Jamison TF (2014) Continuous-flow synthesis of functionalized phenols by aerobic oxidation of grignard reagents. Angew Chem Int Ed 53:3353–3357CrossRef
40.
Zurück zum Zitat Pieber B, Martinez ST, Cantillo D, Kappe CO (2013) In situ generation of diimide from hydrazine and oxygen: continuous-flow transfer hydrogenation of olefins. Angew Chem Int Ed 52:10241–10244CrossRef Pieber B, Martinez ST, Cantillo D, Kappe CO (2013) In situ generation of diimide from hydrazine and oxygen: continuous-flow transfer hydrogenation of olefins. Angew Chem Int Ed 52:10241–10244CrossRef
41.
Zurück zum Zitat Pieber B, Glasnov T, Kappe CO (2015) Continuous flow reduction of artemisinic acid utilizing multi-injection strategies - closing the gap towards a fully continuous synthesis of antimalarial drugs. Chem Eur J 21:4368–4376PubMedCrossRef Pieber B, Glasnov T, Kappe CO (2015) Continuous flow reduction of artemisinic acid utilizing multi-injection strategies - closing the gap towards a fully continuous synthesis of antimalarial drugs. Chem Eur J 21:4368–4376PubMedCrossRef
42.
Zurück zum Zitat Gutmann B, Weigl U, Cox DP, Kappe CO (2016) Batch- and continuous-flow aerobic oxidation of 14-hydroxy opioids to 1,3-oxazolidines – a concise synthesis of noroxymorphone. Chem Eur J 22:10393–10398PubMedCrossRef Gutmann B, Weigl U, Cox DP, Kappe CO (2016) Batch- and continuous-flow aerobic oxidation of 14-hydroxy opioids to 1,3-oxazolidines – a concise synthesis of noroxymorphone. Chem Eur J 22:10393–10398PubMedCrossRef
43.
Zurück zum Zitat Gutmann B, Elsner P, Cox DP et al (2016) Toward the synthesis of noroxymorphone via aerobic palladium-catalyzed continuous flow N-demethylation strategies. ACS Sustain Chem Eng 4:6048–6061CrossRef Gutmann B, Elsner P, Cox DP et al (2016) Toward the synthesis of noroxymorphone via aerobic palladium-catalyzed continuous flow N-demethylation strategies. ACS Sustain Chem Eng 4:6048–6061CrossRef
44.
Zurück zum Zitat Gemoets HPL, Hessel V, Noël T (2014) Aerobic C-H olefination of indoles via a cross-dehydrogenative coupling in continuous flow. Org Lett 16:5800–5803PubMedCrossRef Gemoets HPL, Hessel V, Noël T (2014) Aerobic C-H olefination of indoles via a cross-dehydrogenative coupling in continuous flow. Org Lett 16:5800–5803PubMedCrossRef
45.
Zurück zum Zitat Bourne SL, Ley SV (2013) A continuous flow solution to achieving efficient aerobic anti-Markovnikov Wacker oxidation. Adv Synth Catal 355:1905–1910CrossRef Bourne SL, Ley SV (2013) A continuous flow solution to achieving efficient aerobic anti-Markovnikov Wacker oxidation. Adv Synth Catal 355:1905–1910CrossRef
46.
Zurück zum Zitat Petersen TP, Polyzos A, O’Brien M et al (2012) The oxygen-mediated synthesis of 1,3-butadiynes in continuous flow: using teflon AF-2400 to effect gas/liquid contact. ChemSusChem 5:274–277PubMedCrossRef Petersen TP, Polyzos A, O’Brien M et al (2012) The oxygen-mediated synthesis of 1,3-butadiynes in continuous flow: using teflon AF-2400 to effect gas/liquid contact. ChemSusChem 5:274–277PubMedCrossRef
47.
Zurück zum Zitat Brzozowski M, Forni JA, Savage GP, Polyzos A (2015) The direct α-C(sp3)–H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing. Chem Commun 51:334–337CrossRef Brzozowski M, Forni JA, Savage GP, Polyzos A (2015) The direct α-C(sp3)–H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing. Chem Commun 51:334–337CrossRef
48.
Zurück zum Zitat Park JH, Park CY, Kim MJ et al (2015) Continuous-flow synthesis of meta-substituted phenol derivatives. Org Process Res Dev 19:812–818CrossRef Park JH, Park CY, Kim MJ et al (2015) Continuous-flow synthesis of meta-substituted phenol derivatives. Org Process Res Dev 19:812–818CrossRef
49.
Zurück zum Zitat Brzozowski M, O’Brien M, Ley SV, Polyzos A (2015) Flow chemistry: intelligent processing of gas-liquid transformations using a tube-in-tube reactor. Acc Chem Res 48:349−362CrossRef Brzozowski M, O’Brien M, Ley SV, Polyzos A (2015) Flow chemistry: intelligent processing of gas-liquid transformations using a tube-in-tube reactor. Acc Chem Res 48:349−362CrossRef
50.
Zurück zum Zitat Greene JF, Preger Y, Stahl SS, Root TW (2015) PTFE-membrane flow reactor for aerobic oxidation reactions and its application to alcohol oxidation. Org Process Res Dev 19:858–864CrossRef Greene JF, Preger Y, Stahl SS, Root TW (2015) PTFE-membrane flow reactor for aerobic oxidation reactions and its application to alcohol oxidation. Org Process Res Dev 19:858–864CrossRef
51.
Zurück zum Zitat Plutschack MB, Pieber B, Gilmore K, Seeberger PH (2017) The Hitchhiker’s guide to flow chemistry. Chem Rev 117:11796–11893PubMedCrossRef Plutschack MB, Pieber B, Gilmore K, Seeberger PH (2017) The Hitchhiker’s guide to flow chemistry. Chem Rev 117:11796–11893PubMedCrossRef
52.
Zurück zum Zitat Wootton RCR, Fortt R, De Mello AJ (2002) A microfabricated nanoreactor for safe, continuous generation and use of singlet oxygen. Org Process Res Dev 6:187−189CrossRef Wootton RCR, Fortt R, De Mello AJ (2002) A microfabricated nanoreactor for safe, continuous generation and use of singlet oxygen. Org Process Res Dev 6:187−189CrossRef
53.
Zurück zum Zitat Lumley EK, Dyer CE, Pamme N, Boyle RW (2012) Comparison of photo-oxidation reactions in batch and a new photosensitizer-immobilized microfluidic device. Org Lett 22:5724–5727CrossRef Lumley EK, Dyer CE, Pamme N, Boyle RW (2012) Comparison of photo-oxidation reactions in batch and a new photosensitizer-immobilized microfluidic device. Org Lett 22:5724–5727CrossRef
54.
Zurück zum Zitat Lévesque F, Seeberger PH (2011) Highly efficient continuous flow reactions using singlet oxygen as a “Green” reagent. Org Lett 13:5008–5011PubMedCrossRef Lévesque F, Seeberger PH (2011) Highly efficient continuous flow reactions using singlet oxygen as a “Green” reagent. Org Lett 13:5008–5011PubMedCrossRef
55.
Zurück zum Zitat Lévesque F, Seeberger PH (2012) Continuous-flow synthesis of the anti-malaria drug artemisinin. Angew Chem Int Ed 51:1706–1709CrossRef Lévesque F, Seeberger PH (2012) Continuous-flow synthesis of the anti-malaria drug artemisinin. Angew Chem Int Ed 51:1706–1709CrossRef
56.
Zurück zum Zitat Kopetzki D, Lévesque F, Seeberger PH (2013) A continuous-flow process for the synthesis of artemisinin. Chem Eur J 19:5450–5456PubMedCrossRef Kopetzki D, Lévesque F, Seeberger PH (2013) A continuous-flow process for the synthesis of artemisinin. Chem Eur J 19:5450–5456PubMedCrossRef
57.
Zurück zum Zitat Ushakov DB, Gilmore K, Kopetzki D et al (2014) Continuous-flow oxidative cyanation of primary and secondary amines using singlet oxygen. Angew Chem Int Ed 53:557–561CrossRef Ushakov DB, Gilmore K, Kopetzki D et al (2014) Continuous-flow oxidative cyanation of primary and secondary amines using singlet oxygen. Angew Chem Int Ed 53:557–561CrossRef
58.
Zurück zum Zitat Ushakov DB, Plutschack MB, Gilmore K, Seeberger PH (2015) Factors influencing the regioselectivity of the oxidation of asymmetric secondary amines with singlet oxygen. Chem Eur J 21:6528–6534PubMedCrossRef Ushakov DB, Plutschack MB, Gilmore K, Seeberger PH (2015) Factors influencing the regioselectivity of the oxidation of asymmetric secondary amines with singlet oxygen. Chem Eur J 21:6528–6534PubMedCrossRef
59.
Zurück zum Zitat Cantillo D, Kappe CO (2017) Halogenation of organic compounds using continuous flow and microreactor technology. React Chem Eng 2:7–19CrossRef Cantillo D, Kappe CO (2017) Halogenation of organic compounds using continuous flow and microreactor technology. React Chem Eng 2:7–19CrossRef
60.
Zurück zum Zitat Breen JR, Sandford G, Yufit DS (2011) Continuous gas/liquid-liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination. Beilstein J Org Chem 7:1048–1054PubMedPubMedCentralCrossRef Breen JR, Sandford G, Yufit DS (2011) Continuous gas/liquid-liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination. Beilstein J Org Chem 7:1048–1054PubMedPubMedCentralCrossRef
61.
Zurück zum Zitat Baumann M, Baxendale IR, Martin LJ, Ley SV (2009) Development of fluorination methods using continuous-flow microreactors. Tetrahedron 65:6611–6625CrossRef Baumann M, Baxendale IR, Martin LJ, Ley SV (2009) Development of fluorination methods using continuous-flow microreactors. Tetrahedron 65:6611–6625CrossRef
Metadaten
Titel
Sicherer Umgang mit gefährlichen Chemikalien im Durchfluss
verfasst von
Md Taifur Rahman
Thomas Wirth
Copyright-Jahr
2024
DOI
https://doi.org/10.1007/978-3-031-51912-3_8