1 article(s) from Gambacorta, Guido
Representative shares of the global F&F market (2018) segmented on their applications .
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General structure of an international fragrance company .
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The Michael Edwards fragrance wheel.
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Examples of oriental (1–3), woody (4–7), fresh (8–10), and floral (11 and 12) notes.
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A basic depiction of batch vs flow.
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Examples of reactions for which flow processing outperforms batch.
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Some industrially important aldol-based transformations.
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Biphasic continuous aldol reactions of acetone and various aldehydes.
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Aldol synthesis of 43 in flow using LiHMDS as the base.
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A semi-continuous synthesis of doravirine (49) involving a key aldol reaction.
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Enantioselective aldol reaction using 5-(pyrrolidin-2-yl)tetrazole (51) as catalyst in a microreact...
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Gröger's example of asymmetric aldol reaction in aqueous media.
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Immobilised reagent column reactor types.
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Photoinduced thiol–ene coupling preparation of silica-supported 5-(pyrrolidin-2-yl)tetrazole 63 and...
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Continuous-flow approach for enantioselective aldol reactions using the supported catalyst 67.
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Ötvös’ employment of a solid-supported peptide aldol catalyst in flow.
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The use of proline tetrazole packed in a column for aldol reaction between cyclohexanone (65) and 2...
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Schematic diagram of an aminosilane-grafted Si-Zr-Ti/PAI-HF reactor for continuous-flow aldol and n...
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Continuous-flow condensation for the synthesis of the intermediate 76 to nabumetone (77) and Microi...
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Synthesis of ψ-Ionone (80) in continuous-flow via aldol condensation between citral (79) and aceton...
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Synthesis of β-methyl-ionones (83) from citral (79) in flow. The steps are separately described, an...
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Continuous-flow synthesis of 85 from 84 described by Gavriilidis et al.
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Continuous-flow scCO2 apparatus for the synthesis of 2-methylpentanal (87) and the self-condensed u...
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Chen’s two-step flow synthesis of coumarin (90).
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Pechmann condensation for the synthesis of 7-hydroxyxcoumarin (93) in flow. The setup extended to c...
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Synthesis of the dihydrojasmonate 35 exploiting nitro derivative proposed by Ballini et al.
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Silica-supported amines as heterogeneous catalyst for nitroaldol condensation in flow.
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Flow apparatus for the nitroaldol condensation of p-hydroxybenzaldehyde (102) to nitrostyrene 103 a...
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Nitroaldol reaction of 64 to 105 employing a quaternary ammonium functionalised PANF.
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Enantioselective nitroaldol condensation for the synthesis of 108 under flow conditions.
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Enatioselective synthesis of 1,2-aminoalcohol 110 via a copper-catalysed nitroaldol condensation.
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Examples of Knoevenagel condensations applied for fragrance components.
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Flow apparatus for Knoevenagel condensation described in 1989 by Venturello et al.
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Knoevenagel reaction using a coated multichannel membrane microreactor.
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Continuous-flow apparatus for Knoevenagel condensation employing sugar cane bagasse as support deve...
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Knoevenagel reaction for the synthesis of 131–135 in flow using an amine-functionalised silica gel. ...
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Continuous-flow synthesis of compound 137, a key intermediate for the synthesis of pregabalin (138)...
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Continuous solvent-free apparatus applied for the synthesis of compounds 140–143 using a TSE. Throu...
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Lewis et al. developed a spinning disc reactor for Darzens condensation of 144 and a ketone to furn...
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Some key industrial applications of conjugate additions in the F&F industry.
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Continuous-flow synthesis of 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide (156) via double conjugat...
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Continuous-flow system for Michael addition using CsF on alumina as the catalyst.
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Calcium chloride-catalysed asymmetric Michael addition using an immobilised chiral ligand.
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Continuous multistep synthesis for the preparation of (R)-rolipram (173). Si-NH2: primary amine-fun...
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Continuous-flow Michael addition using ion exchange resin Amberlyst® A26.
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Preparation of the heterogeneous catalyst 181 developed by Paixão et al. exploiting Ugi multicompon...
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Continuous-flow system developed by the Paixão’s group for the preparation of Michael asymmetric ad...
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Continuous-flow synthesis of nitroaldols catalysed by supported catalyst 184 developed by Wennemers...
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Heterogenous polystyrene-supported catalysts developed by Pericàs and co-workers.
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PANF-supported pyrrolidine catalyst for the conjugate addition of cyclohexanone (65) and trans-β-ni...
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Synthesis of (−)-paroxetine precursor 195 developed by Ötvös, Pericàs, and Kappe.
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Continuous-flow approach for the 5-step synthesis of (−)-oseltamivir (201) as devised by Hayashi an...
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Continuous-flow enzyme-catalysed Michael addition.
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Continuous-flow copper-catalysed 1,4 conjugate addition of Grignard reagents to enones. Reprinted w...
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A collection of commonly encountered hydrogenation reactions.
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The ThalesNano H-Cube® continuous-flow hydrogenator.
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Chemoselective reduction of an α,β-unsaturated ketone using the H-Cube® reactor.
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Incorporation of Lindlar’s catalyst into the H-Cube® reactor for the reduction of an alkyne.
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Continuous-flow semi-hydrogenation of alkyne 208 to 209 using SACs with H-Cube® system.
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The standard setups for tube-in-tube gas–liquid reactor units.
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Homogeneous hydrogenation of olefins using a tube-in-tube reactor setup.
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Recyclable heterogeneous flow hydrogenation system.
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Leadbeater’s reverse tube-in-tube hydrogenation system for olefin reductions.
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a) Hydrogenation using a Pd-immobilised microchannel reactor (MCR) and b) a representation of the i...
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Hydrogenation of alkyne 238 exploiting segmented flow in a Pd-immobilised capillary reactor.
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Continuous hydrogenation system for the preparation of cyrene (241) from (−)-levoglucosenone (240).
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Continuous hydrogenation system based on CSMs developed by Hornung et al.
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Chemoselective reduction of carbonyls (ketones over aldehydes) in flow.
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Continuous system for the semi-hydrogenation of 256 and 258, developed by Galarneau et al.
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Continuous synthesis of biodiesel fuel 261 from lignin-derived furfural acetone (260).
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Continuous synthesis of γ-valerolacetone (263) via CTH developed by Pineda et al.
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Continuous hydrogenation of lignin-derived biomass (products 265, 266, and 267) using a sustainable...
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Ru/C or Rh/C-catalysed hydrogenation of arene in flow as developed by Sajiki et al.
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Polysilane-immobilized Rh–Pt-catalysed hydrogenation of arenes in flow by Kobayashi et al.
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High-pressure in-line mixing of H2 for the asymmetric reduction of 278 at pilot scale with a 73 L p...
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Picture of the PFR employed at Eli Lilly & Co. for the continuous hydrogenation of 278 . Reprinted ...
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Continuous-flow asymmetric hydrogenation using Oppolzer's sultam 280 as chiral auxiliary.
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Some examples of industrially important oxidation reactions in the F&F industry. CFL: compact fluor...
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Gold-catalysed heterogeneous oxidation of alcohols in flow.
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Uozumi’s ARP-Pt flow oxidation protocol.
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High-throughput screening of aldehyde oxidation in flow using an in-line GC.
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Permanganate-mediated Nef oxidation of nitroalkanes in flow with the use of in-line sonication to p...
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Continuous-flow aerobic anti-Markovnikov Wacker oxidation.
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Continuous-flow oxidation of 2-benzylpyridine (312) using air as the oxidant.
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Continuous-flow photo-oxygenation of monoterpenes.
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A tubular reactor design for flow photo-oxygenation.
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Glucose oxidase (GOx)-mediated continuous oxidation of glucose using compressed air and the FFMR re...
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Schematic continuous-flow sodium hypochlorite/TEMPO oxidation of alcohols.
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Oxidation using immobilised TEMPO (344) was developed by McQuade et al.
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General protocol for the bleach/catalytic TBAB oxidation of aldehydes and alcohols.
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Continuous-flow PTC-assisted oxidation using hydrogen peroxide. The process was easily scaled up by...
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Continuous-flow epoxidation of cyclohexene (348) and in situ preparation of m-CPBA.
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Continuous-flow epoxidation using DMDO as oxidant.
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Mukayama aerobic epoxidation optimised in flow mode by the Favre-Réguillon group.
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Continuous-flow asymmetric epoxidation of derivatives of 359 exploiting a biomimetic iron catalyst.
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Continuous-flow enzymatic epoxidation of alkenes developed by Watts et al.
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Engineered multichannel microreactor for continuous-flow ozonolysis of 366.
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Continuous-flow synthesis of the vitamin D precursor 368 using multichannel microreactors. MFC: mas...
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Continuous ozonolysis setup used by Kappe et al. for the synthesis of various substrates employing ...
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Continuous-flow apparatus for ozonolysis as developed by Ley et al.
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Continuous-flow ozonolysis for synthesis of vanillin (2) using a film-shear flow reactor.
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Examples of preparative methods for ajoene (386) and allicin (388).
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Continuous-flow oxidation of thioanisole (389) using styrene-based polymer-supported peroxytungstat...
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Continuous oxidation of thiosulfinates using Oxone®-packed reactor.
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Continuous-flow electrochemical oxidation of thioethers.
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Continuous-flow oxidation of 400 to cinnamophenone (235).
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Continuous-flow synthesis of dehydrated material 401 via oxidation of methyl dihydrojasmonate (33).
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Some industrially important transformations involving Grignard reagents.
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Grachev et al. apparatus for continuous preparation of Grignard reagents.
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Example of fluidized Mg bed reactor with NMR spectrometer as on-line monitoring system.
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Continuous-flow synthesis of Grignard reagents and subsequent quenching reaction.
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Membrane-based, liquid–liquid separator with integrated pressure control . Adapted with permission ...
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Continuous-flow synthesis of 458, an intermediate to fluconazole (459).
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Continuous-flow synthesis of ketones starting from benzoyl chlorides.
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A Grignard alkylation combining CSTR and PFR technologies with in-line infrared reaction monitoring....
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Continuous-flow preparation of 469 from Grignard addition of methylmagnesium bromide.
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Continuous-flow synthesis of Grignard reagents 471.
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Preparation of the Grignard reagent 471 using CSTR and the continuous process for synthesis of the ...
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Continuous process for carboxylation of Grignard reagents in flow using tube-in-tube technology.
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Continuous synthesis of propargylic alcohols via ethynyl-Grignard reagent.
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Silica-supported catalysed enantioselective arylation of aldehydes using Grignard reagents in flow ...
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Acid-catalysed rearrangement of citral and dehydrolinalool derivatives.
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Continuous stilbene isomerisation with continuous recycling of photoredox catalyst.
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Continuous-flow synthesis of compound 494 as developed by Ley et al.
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Selected industrial applications of DA reaction.
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Multistep flow synthesis of the spirocyclic structure 505 via employing DA cycloaddition.
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Continuous-flow DA reaction developed in a plater flow reactor for the preparation of the adduct 508...
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Continuous-flow DA reaction using a silica-supported imidazolidinone organocatalyst.
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Batch vs flow for the DA reaction of (cyclohexa-1,5-dien-1-yloxy)trimethylsilane (513) with acrylon...
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Continuous-flow DA reaction between 510 and 515 using a shell-core droplet system.
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Continuous-flow synthesis of bicyclic systems from benzyne precursors.
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Continuous-flow synthesis of bicyclic scaffolds 527 and 528 for further development of potential ph...
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Continuous-flow inverse-electron hetero-DA reaction to pyridine derivatives such as 531.
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Comparison between batch and flow for the synthesis of pyrimidinones 532–536 via retro-DA reaction ...
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Continuous-flow coupled with ultrasonic system for preparation of ʟ-ascorbic acid derivatives 539 d...
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Two-step continuous-flow synthesis of triazole 543.
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Continuous-flow preparation of triazoles via CuAAC employing 546-based heterogeneous catalyst.
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Continuous-flow synthesis of compounds 558 through A3-coupling and 560 via AgAAC both employing the...
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Continuous-flow photoinduced [2 + 2] cycloaddition for the preparation of bicyclic derivatives of 5...
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Continuous-flow [2 + 2] and [5 + 2] cycloaddition on large scale employing a flow reactor developed...
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Continuous-flow preparation of the tricyclic structures 573 and 574 starting from pyrrole 570 via [...
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Continuous-flow [2 + 2] photocyclization of cinnamates.
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Continuous-flow preparation of cyclobutane 580 on a 5-plates photoreactor.
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Continuous-flow [2 + 2] photocycloaddition under white LED lamp using heterogeneous PCN as photocat...
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Picture of the parallel tube flow reactor (PTFR) "The Firefly" developed by Booker-Milburn et al. a...
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Continuous-flow acid-catalysed [2 + 2] cycloaddition between silyl enol ethers and acrylic esters.
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Continuous synthesis of lactam 602 using glass column reactors.
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In situ generation of ketenes for the Staudinger lactam synthesis developed by Ley and Hafner.
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Application of [2 + 2 + 2] cycloadditions in flow employed by Ley et al.
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Examples of FC reactions applied in F&F industry.
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Continuous-flow synthesis of ibuprofen developed by McQuade et al.
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The FC acylation step of Jamison’s three-step ibuprofen synthesis.
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Synthesis of naphthalene derivative 629 via FC acylation in microreactors.
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Flow system for rapid screening of catalysts and reaction conditions developed by Weber et al.
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Continuous-flow system developed by Buorne, Muller et al. for DSD optimisation of the FC acylation ...
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Continuous-flow FC acylation of alkynes to yield β-chlorovinyl ketones such as 638.
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Continuous-flow synthesis of tonalide (619) developed by Wang et al.
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Continuous-flow preparation of acylated arene such as 290 employing Zr4+-β-zeolite developed by Kob...
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Flow system applied on an Aza-FC reaction catalysed by the thiourea catalyst 648.
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Continuous hydroformylation in scCO2.
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Two-step flow synthesis of aldehyde 655 through a sequential Heck reaction and subsequent hydroform...
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Single-droplet (above) and continuous (below) flow reactors developed by Abolhasani et al. for the ...
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Continuous hydroformylation of 1-dodecene (655) using a PFR-CSTR system developed by Sundmacher et ...
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Continuous-flow synthesis of the aldehyde 660 developed by Eli Lilly & Co. . Adapted with permissio...
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Continuous asymmetric hydroformylation employing heterogenous catalst supported on carbon-based sup...
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Examples of acetylation in F&F industry: synthesis of bornyl (S,R,S-664) and isobornyl (S,S,S-664) ...
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Continuous-flow preparation of bornyl acetate (S,R,S-664) employing the oscillating flow reactor.
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Continuous-flow synthesis of geranyl acetate (666) from acetylation of geraniol (343) developed by ...
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12-Ttungstosilicic acid-supported silica monolith-catalysed acetylation in flow.
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Continuous-flow preparation of cyclopentenone 676.
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Two-stage synthesis of coumarin (90) via acetylation of salicylaldehyde (88).
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Intensification process for acetylation of 5-methoxytryptamine (677) to melatonin (678) developed b...
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Examples of macrocyclic musky odorants both natural (679–681) and synthetic (682 and 683).
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Flow setup combined with microwave for the synthesis of macrocycle 686 via RCM.
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Continuous synthesis of 2,5-dihydro-1H-pyrroles via ring-closing metathesis.
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Continuous-flow metathesis of 485 developed by Leadbeater et al.
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Comparison between RCM performed using different routes for the preparation of 696. On the left the...
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Continuous-flow RCM of 697 employed the solid-supported catalyst 698 developed by Grela, Kirschning...
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Continuous-flow RORCM of cyclooctene employing the silica-absorbed catalyst 700.
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Continuous-flow self-metathesis of methyl oleate (703) employing SILP catalyst 704.
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Flow apparatus for the RCM of 697 using a nanofiltration membrane for the recovery and reuse of the...
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Comparison of loadings between RCMs performed with different routes for the synthesis of 709.
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Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90
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