{"title":"The applications of organozinc reagents in continuous flow chemistry: Negishi coupling","authors":"Roop Varghese Rubert, Rony Rajan Paul","doi":"10.1007/s41981-022-00253-x","DOIUrl":"10.1007/s41981-022-00253-x","url":null,"abstract":"<div><p>The design and implementation of flow technique helps organic chemists to resolve numerous challenges that are encountered during various catalytic reactions. Flow technologies, which offer solutions for technical and/or chemical issues, have gained popularity over the last two decades in the field of organic chemistry. The selectivity, efficiency, and safety of the entire process has been accelerated by flow reactors as they improve mass and heat transfer, speeds up the mixing of the reaction, and they offer exact control of the reaction parameters. This review mainly describes the utilization of flow chemistry in reactions involving organiozinc reagent, particularly Negishi coupling. The Negishi coupling of organozinc reagent is a valuable tool for the formation of C-C bond with functional group tolerance and are used extensively in total synthesis. This review also portrays a comparative study of organozinc reagents prepared using different procedures. A study of the effect of different catalysts over the same reaction is also carried out. An overview of different flow techniques that are employed has also been incorporated.</p></div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 3","pages":"217 - 246"},"PeriodicalIF":2.7,"publicationDate":"2023-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4496032","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bi Bali Judicaël Tra, Abollé Abollé, Killian Lucas, François-Xavier Felpin
{"title":"Electrophilic cyclization of reticuline-type alkaloids in flow via o-quinol intermediates","authors":"Bi Bali Judicaël Tra, Abollé Abollé, Killian Lucas, François-Xavier Felpin","doi":"10.1007/s41981-022-00256-8","DOIUrl":"10.1007/s41981-022-00256-8","url":null,"abstract":"<p>Herein, we report the first continuous-flow biomimetic cyclization of reticuline derivatives to aporphine alkaloids via <i>ortho</i>-quinol intermediates. The two-step flow process involves an initial oxidative dearomatization of reticuline derivatives to using hypervalent iodine(III) reagents, followed by a TMSOTf-mediated electrophilic cyclization. The high sensitivity of <i>ortho</i>-quinol compounds is mitigated by the mild experimental conditions and fast reaction rates offered by flow reactors. A preliminary structure–reactivity relationship suggests that both steps of the process are favored with strongly electron-rich substrates, similar to what is observed in nature.</p>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 3","pages":"257 - 265"},"PeriodicalIF":2.7,"publicationDate":"2023-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4492752","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Selective monosubstitution on a trichlorosilane with highly reactive organolithium compounds in a microflow reactor","authors":"Moritz Achternbosch, Lukas Zibula, Annika Schmidt, Waldemar Krieger, Norbert Kockmann, Carsten Strohmann","doi":"10.1007/s41981-022-00254-w","DOIUrl":"10.1007/s41981-022-00254-w","url":null,"abstract":"<div><p>Organolithium compounds have been used successfully in flow chemistry since the recent past. Most of the studies dealt with the use in halogen-lithium exchanges. So far, however, there has been a lack of use in substitution reactions. The use of flow microreactors makes the highly reactive organolithium compounds more controllable and thus creates new synthetic possibilities.</p></div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 1","pages":"9 - 12"},"PeriodicalIF":2.7,"publicationDate":"2022-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s41981-022-00254-w.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5034487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Timothy Aljoscha Frede, Nick Nikbin, Norbert Kockmann
{"title":"Reactor performance estimation in microscale flow calorimeter for rapid characterization of exothermic reactions","authors":"Timothy Aljoscha Frede, Nick Nikbin, Norbert Kockmann","doi":"10.1007/s41981-022-00251-z","DOIUrl":"10.1007/s41981-022-00251-z","url":null,"abstract":"<p>Continuous flow calorimeters are a promising tool in process development and safety engineering, especially for flow chemistry applications to characterize the heat release and kinetic parameters of rapid chemical reactions. In this study, the digital accompaniment of an isoperibolic flow calorimeter for characterization of exothermic reactions is presented. To support experimental planning and evaluation, computational fluid dynamic simulations are carried out for single-phase flow in the microreactor. The residence time distribution is obtained and used for estimation of conversion and temperature profiles along the microreactor channel. This leads to an integration of CFD simulations into the calorimeter’s software-guided workflow reducing the experimental effort regarding the determination of thermokinetic data. The approach is tested for a highly exothermic test reaction, which provides further hints for future investigations.</p>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 1","pages":"31 - 44"},"PeriodicalIF":2.7,"publicationDate":"2022-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s41981-022-00251-z.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4485662","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"TfOH-catalyzed three-component synthesis of Dithiocarbamates from α-Diazoesters under continuous flow conditions","authors":"Rui Wang, Hangli He, Qiongjiao Yan, Wei Wang, Haifeng Wang, Fener Chen","doi":"10.1007/s41981-022-00249-7","DOIUrl":"10.1007/s41981-022-00249-7","url":null,"abstract":"<div><p>The synthesis of dithiocarbamates derivatives is important for their practical utilization as pharmaceuticals and for other purposes. Herein, we demonstrated the TfOH-catalyzed synthesis of dithiocarbamates via three-component reaction of <i>α</i>-diazoesters in good yields under continuous flow conditions. The reaction exhibits a wide substrate scope of diazo compounds and high functional group tolerance. This study provides a safe and mild protocol to form dithiocarbamates that complements TfOH-catalyzed S-H insertion reaction of diazo compounds and continuous flow synthesis strategies.</p></div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 1","pages":"1 - 8"},"PeriodicalIF":2.7,"publicationDate":"2022-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4489614","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Minireview: recent efforts toward upgrading lignin-derived phenols in continuous flow","authors":"Erin E. Brown","doi":"10.1007/s41981-022-00248-8","DOIUrl":"10.1007/s41981-022-00248-8","url":null,"abstract":"<div><p>Phenols are vital building blocks for manufactured goods, agrochemicals, and medicine. As the demand to circumvent fossil fuels intensifies, so does the need to establish alternate sources of chemical feedstock, with many researchers looking to biomass. Lignin, a complex biopolymer found in plants, represents a relatively untapped renewable source of phenolic compounds. Examples of aromatic compounds derived from lignin include phenol, guaiacol (2-methoxyphenol), and catechol (2-hydroxyphenol). The development of new technologies and chemistry to upgrade or modify these compounds is crucial to realizing the potential of biomass as chemical feedstock. Over the last two decades, continuous flow technology has become an established tool for chemists to expand the capabilities of reaction control and to provide a means to probe novel reactions that might otherwise be difficult to study or accomplish via conventional means. Flow also imparts many advantages, such as superior mixing capabilities for gas/liquid reactions, increased efficiency for photochemical transformations, and improved scalability. This mini review will highlight research efforts reported in the last half-decade (since 2016) toward <i>upgrading lignin-derived phenolic substrates using continuous flow technology</i>. Recent developments focus on reactions requiring oxygenation, oxidation, hydrogenation, and deoxygenation to name a few.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 2","pages":"91 - 102"},"PeriodicalIF":2.7,"publicationDate":"2022-12-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4204213","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Mediated formic acid flow fuel cell (MFAFFC) based on biomimetic electrolytes","authors":"Katerina Bretosh, Mathieu Beaucamp, Florine Toulotte, Jinyi Yuan, Philippe Hapiot, Maël Penhoat","doi":"10.1007/s41981-022-00245-x","DOIUrl":"10.1007/s41981-022-00245-x","url":null,"abstract":"<div><p>Water soluble biomimetic models of Riboflavin (B2 vitamin) and Folic acid (B8 vitamin) demonstrated to be good oxidant of formic acid at various pH. Their usage as anolyte mediators in a flow fuel cell to convert formic acid (or formate) into electricity is validated with measured power densities up to 16 mW.cm<sup>− 2</sup>. These preliminary optimum conditions demonstrated a volumetric energy density of 0.68 Wh.L<sup>− 1</sup> when operating at 5 mA.cm<sup>− 2</sup> and neutral pH. These new conditions inspired from redox flow batteries processes permit to remove noble metals at both sides of the formate flow fuel cell.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 2","pages":"133 - 142"},"PeriodicalIF":2.7,"publicationDate":"2022-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4073362","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ha Bich Phan, Trinh Hao Nguyen, Diep Dinh Le, Nhi Hoang Nguyen, Tan Van Nguyen, Phuong Hoang Tran
{"title":"Continuous flow synthesis of HMF from glucose using gadolinium (III) trifluoromethanesulfonate in Brønsted acidic ionic liquid as a catalytic system","authors":"Ha Bich Phan, Trinh Hao Nguyen, Diep Dinh Le, Nhi Hoang Nguyen, Tan Van Nguyen, Phuong Hoang Tran","doi":"10.1007/s41981-022-00250-0","DOIUrl":"10.1007/s41981-022-00250-0","url":null,"abstract":"<div><p>The direct conversion of glucose to 5-(hydroxymethyl)furfural (HMF) has been considered a challenging process. In this study, we developed a new method using gadolinium(III) trifluoromethanesulfonate (Gd(OTf)<sub>3</sub>) in combination with Brønsted acidic ionic liquids as a catalytic system to search possibly more environmentally benign process. The reaction was carried out under a continuous-flow system. The one-step isomerization/dehydration of glucose to give the highest HMF with Gd(OTf)<sub>3</sub> together with DBU-based Brønsted acidic ionic liquid in a low-cost home-built continuous system. The plausible mechanism was proposed with the Lewis acidic sites of Gd(OTf)<sub>3</sub> for the isomerization step and DBU-based Brønsted acidic ionic liquid sites for the dehydration step. The recycling of catalytic system Gd(OTf)<sub>3</sub>/DBU-based Brønsted acidic ionic liquid in DMSO was examined. Our findings provided a safe and environmental process for the continuous conversion of glucose into HMF. The use of continuous flow for HMF synthesis ensures that the current method can be applied to the large-scale process.</p></div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 2","pages":"121 - 132"},"PeriodicalIF":2.7,"publicationDate":"2022-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5133123","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Geoffroy Kaisin, Loïc Bovy, Yoann Joyard, Nicolas Maindron, Vincent Tadino, Jean-Christophe M. Monbaliu
{"title":"A perspective on automated advanced continuous flow manufacturing units for the upgrading of biobased chemicals toward pharmaceuticals","authors":"Geoffroy Kaisin, Loïc Bovy, Yoann Joyard, Nicolas Maindron, Vincent Tadino, Jean-Christophe M. Monbaliu","doi":"10.1007/s41981-022-00247-9","DOIUrl":"10.1007/s41981-022-00247-9","url":null,"abstract":"<div><p>Biomass is a renewable, almost infinite reservoir of a large diversity of highly functionalized chemicals. The conversion of biomass toward biobased platform molecules through biorefineries generally still lacks economic viability. Profitability could be enhanced through the development of new market opportunities for these biobased platform chemicals. The fine chemical industry, and more specifically the manufacturing of pharmaceuticals is one of the sectors bearing significant potential for these biobased building blocks to rapidly emerge and make a difference. There are, however, still many challenges to be dealt with before this market can thrive. Continuous flow technology and its integration for the upgrading of biobased platform molecules for the manufacturing of pharmaceuticals is foreseen as a game-changer. This perspective reflects on the main challenges relative to chemical, process, regulatory and supply chain-related burdens still to be addressed. The implementation of integrated continuous flow processes and their automation into modular units will help for tackling with these challenges.</p><h3>Graphical abstract</h3>\u0000 <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\u0000 </div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 2","pages":"77 - 90"},"PeriodicalIF":2.7,"publicationDate":"2022-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s41981-022-00247-9.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5133518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Guillaume Reynard, Eric Wimmer, Jérémi Richelet, Jean-Marie Fourquez, Hélène Lebel
{"title":"Chemoselective borylation of bromoiodoarene in continuous flow: synthesis of bromoarylboronic acids","authors":"Guillaume Reynard, Eric Wimmer, Jérémi Richelet, Jean-Marie Fourquez, Hélène Lebel","doi":"10.1007/s41981-022-00246-w","DOIUrl":"10.1007/s41981-022-00246-w","url":null,"abstract":"<p>The chemoselective borylation of bromoiodoarenes under continuous flow conditions is described. Bromoarylboronic acids were synthesized in high yields using <i>i</i>PrMgCl•LiCl as the halogen-metal exchange reagent, with 5.7–86 s residence time at room temperature. The process is compatible with a variety of functional groups, including carbanion-reactive moieties, enabling post-product functionalization. A gram-scale reaction, including a continuous-flow work-up, afforded the desired product in a highly efficient manner. Successful telescoping with a Suzuki coupling has also been performed, converting 1-bromo-3-iodobenzene to 3-bromo-1,1′-biphenyl on a gram-scale in a good yield.</p>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"13 1","pages":"21 - 29"},"PeriodicalIF":2.7,"publicationDate":"2022-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s41981-022-00246-w.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"4905811","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}