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Abbreviations
- Ac:
-
Acetyl
- acac:
-
Acetylacetonate
- ATR:
-
Attenuated total reflection
- bpy:
-
2,2′-Bipyridyl
- conv:
-
Conversion
- CSTR:
-
Continuous stirred-tank reactor
- DBU:
-
1,8-Diazabicyclo[5.4.0]undec-7-ene
- DMF:
-
N,N-dimethylformamide
- DMSO:
-
Dimethylsulfoxide
- dr:
-
Diastereomeric ratio
- equiv:
-
Equivalent(s)
- Et:
-
Ethyl
- EXAFS:
-
Extended X-ray absorption fine structure
- FDH:
-
Formate dehydrogenase
- FEP:
-
Fluorinated ethylene propylene
- g:
-
Gram(s)
- GC:
-
Gas chromatography
- h:
-
Hour(s)
- HbpA:
-
2-Hydroxybiphenyl 3-monooxygenase
- HPLC:
-
High-performance liquid chromatography
- IBX:
-
2-Iodoxybenzoic acid
- i-Pr:
-
iso-Propyl
- IR:
-
Infrared
- L:
-
Liter(s)
- LED:
-
Light-emitting diode
- LOC:
-
Limiting oxygen concentration
- m:
-
Meter(s)
- M:
-
Molar
- Me:
-
Methyl
- MFC:
-
Mass flow controller
- min:
-
Minute(s)
- mol:
-
Mole(s)
- MS:
-
Mass spectrometry
- NAD:
-
Nicotinamide adenine dinucleotide
- NaHMDS:
-
Sodium hexamethyldisilazide
- NMI:
-
N-Methylimidazole
- NMO:
-
N-Methylmorpholine N-oxide
- NMP:
-
N-Methyl-2-pyrrolidone
- n-Pr:
-
n-Propyl
- PCC:
-
Pyridiniumchlorochromate
- PDC:
-
Pyridinium dichromate
- PDMS:
-
Polydimethylsiloxane
- PEEK:
-
Polyether ether ketone
- PEG:
-
Polyethylene glycol
- PFA:
-
Perfluoroalkoxy
- Ph:
-
Phenyl
- phen:
-
Phenanthroline
- PTFE:
-
Polytetrafluoroethylene
- quant:
-
Quantitative
- rt:
-
Room temperature
- s:
-
Second(s)
- sc:
-
Supercritical
- Sel:
-
Selectivity
- SET:
-
Single-electron transfer
- SMU:
-
Static mixing unit
- t-AmOK:
-
Potassium tert-amylate
- TBAF:
-
Tetrabutylammonium fluoride
- TBR:
-
Trickle-bed reactor
- t-bu:
-
tert-Butyl
- TEM:
-
Transmission electron microscopy
- TEMPO:
-
(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl
- TEOS:
-
Tetraethoxysilane
- Tf:
-
Trifluoromethanesulfonyl
- TFA:
-
Trifluoroacetic acid
- THF:
-
Tetrahydrofuran
- TMEDA:
-
N,N,N′,N′-Tetramethyl-1,2-ethylenediamine
- TMSCN:
-
Trimethylsilylcyanide
- TPAP:
-
Tetrapropylammoniumperuthenate
- TPP:
-
meso-Tetraphenylporphyrin
- U:
-
Unit(s)
- UHP:
-
Urea hydrogen peroxide
- XAS:
-
X-ray absorption spectroscopy
References
Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC (2013) Chem Rev 113:6234
Campbell AN, Stahl SS (2012) Acc Chem Res 45:851
Cao Q, Dornan LM, Rogan L, Hughes NL, Muldoon MJ (2014) Chem Commun 50:4524
Davis SE, Ide MS, Davis RJ (2013) Green Chem 15:17
Wendlandt AE, Suess AM, Stahl SS (2011) Angew Chem Int Ed 50:11062
Osterberg PM, Niemeier JK, Welch CJ, Hawkins JM, Martinelli JR, Johnson TE, Root TW, Stahl SS (2015) Org Process Res Dev. doi:10.1021/op500328f
Hessel V, Kralisch D, Kockmann N, Noel T, Wang Q (2013) ChemSusChem 6:746
Wiles C, Watts P (2014) Green Chem 16:55
Vaccaro L, Lanari D, Marrocchi A, Strappaveccia G (2014) Green Chem 16:3680
Jensen KF, Reizman BJ, Newman SG (2014) Lab Chip 14:3206
Pastre JC, Browne DL, Ley SV (2013) Chem Soc Rev 42:8849
McQuade DT, Seeberger PH (2013) J Org Chem 78:6384
Baxendale IR, Brocken L, Mallia CJ (2013) Green Process Synth 2:211
Gutmann B, Cantillo D, Kappe CO (2015) Angew Chem Int Ed 54:6688
Jahnisch K, Hessel V, Lowe H, Baerns M (2004) Angew Chem Int Ed 43:406
Inoue T, Schmidt MA, Jensen KF (2007) Ind Eng Chem Res 46:1153
Noel T, Hessel V (2013) ChemSusChem 6:405
Kolb G, Hessel V, Cominos V, Hofmann C, Lowe H, Nikolaidis G, Zapf R, Ziogas A, Delsman ER, de Croon MHJM, Schouten JC, de la Iglesia O, Mallada R, Santamaria J (2007) Catal Today 120:2
Roydhouse MD, Ghaini A, Constantinou A, Cantu-Perez A, Motherwell WB, Gavriilidis A (2011) Org Process Res Dev 15:989
Nobis M, Roberge DM (2011) Chim Oggi 29:56
Irfan M, Glasnov TN, Kappe CO (2011) Org Lett 13:984
Brzozowski M, O‘Brien M, Ley SV, Polyzos A (2015) Acc Chem Res 48:349
Yang L, Jensen KF (2013) Org Process Res Dev 17:927
Munirathinam R, Huskens J, Verboom W (2015) Adv Synth Catal 357:1093
Schmieder H, Abeln J (1999) Chem Eng Technol 22:903
Tomas RAF, Bordado JCM, Gomes JFP (2013) Chem Rev 113:7421
Hamley PA, Ilkenhans T, Webster JM, Garcia-Verdugo E, Venardou E, Clarke MJ, Auerbach R, Thomas WB, Whiston K, Poliakoff M (2002) Green Chem 4:235
Garcia-Verdugo E, Venardou E, Thomas WB, Whiston K, Partenheimer W, Hamley PA, Poliakoff M (2004) Adv Synth Catal 346:307
Fraga-Dubreuil J, Garcia-Verdugo E, Hamley PA, Vaquero EM, Dudd LM, Pearson I, Housley D, Partenheimer W, Thomas WB, Whiston K, Poliakoff M (2007) Green Chem 9:1238
Garcia-Verdugo E, Fraga-Dubreuil J, Hamley PA, Thomas WB, Whiston K, Poliakoff M (2005) Green Chem 7:294
Fraga-Dubreuil J, Garcia-Verdugo E, Hamley PA, Perez E, Pearson I, Thomas WB, Housley D, Partenheimer W, Poliakoff M (2009) Adv Synth Catal 351:1866
Perez E, Fraga-Dubreuil J, Garcia-Verdugo E, Hamley PA, Thomas WB, Housley D, Partenheimer W, Poliakoff M (2011) Green Chem 13:2389
Perez E, Fraga-Dubreuil J, Garcia-Verdugo E, Hamley PA, Thomas ML, Yan C, Thomas WB, Housley D, Partenheimer W, Poliakoff M (2011) Green Chem 13:2397
Gutmann B, Elsner P, Roberge D, Kappe CO (2013) ACS Catal 3:2669
Pieber B, Kappe CO (2013) Green Chem 15:320
De Houwer J, Tehrani KA, Maes BUW (2012) Angew Chem Int Ed 51:2745
Hamano M, Nagy KD, Jensen KF (2012) Chem Commun 48:2086
Neuenschwander U, Jensen KF (2014) Ind Eng Chem Res 53:601
Musser MT (2000) Cyclohexanol and cyclohexanone Ullmann‘s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim, Germany
Leclerc A, Alame M, Schweich D, Pouteau P, Delattre C, de Bellefon C (2008) Lab Chip 8:814
Fischer J, Lange T, Boehling R, Rehfinger A, Klemm E (2010) Chem Eng Sci 65:4866
Bourne SL, Ley SV (2013) Adv Synth Catal 355:1905
Tomaszewski B, Lloyd RC, Warr AJ, Buehler K, Schmid A (2014) ChemCatChem 6:2567
Tomaszewski B, Schmid A, Buehler K (2014) Org Process Res Dev 18:1516
LaPorte TL, Hamedi M, DePue JS, Shen LF, Watson D, Hsieh D (2008) Org Process Res Dev 12:956
Zhan BZ, Thompson A (2004) Tetrahedron 60:2917
Schultz MJ, Sigman MS (2006) Tetrahedron 62:8227
Parmeggiani C, Cardona F (2012) Green Chem 14:547
Ryland BL, Stahl SS (2014) Angew Chem Int Ed 53:8824
Felthouse TR (1987) J Am Chem Soc 109:7566
Felthouse TR, Fraundorf PB, Friedman RM, Schosser CL (1991) J Catal 127:393
Kimura H (1993) Appl Catal A-Gen 105:147
Bavykin DV, Lapkin AA, Kolaczkowski ST, Plucinski PK (2005) Appl Catal A-Gen 288:175
Bavykin DV, Lapkin AA, Plucinski PK, Friedrich JM, Walsh FC (2005) J Catal 235:10
Plucinski PK, Bavykin DV, Kolaczkowski ST, Lapkin AA (2005) Ind Eng Chem Res 44:9683
Plucinski PK, Bavykin DV, Kolaczkowski ST, Lapkin AA (2005) Catal Today 105:479
Zotova N, Hellgardt K, Kelsall GH, Jessiman AS, Hii KK (2010) Green Chem 12:2157
Obermayer D, Balu AM, Romero AA, Goessler W, Luque R, Kappe CO (2013) Green Chem 15:1530
Liu XY, Jensen KF (2013) Green Chem 15:1538
Liu XY, Jensen KF (2012) Green Chem 14:1471
Mannel DS, Stahl SS, Root TW (2014) Org Process Res Dev 18:1503
Cao EH, Motherwell WB, Gavriilidis A (2006) Chem Eng Technol 29:1372
Cao E, Gavriilidis A, Motherwell WB (2004) Chem Eng Sci 59:4803
Muzen A, Fraguio MS, Cassanello MC, Ayude MA, Haure PM, Martinez OM (2005) Ind Eng Chem Res 44:5275
Tarasov AL, Kustov LM, Bogolyubov AA, Kiselyov AS, Semenov VV (2009) Appl Catal A-Gen 366:227
Brandner A, Lehnert K, Bienholz A, Lucas M, Claus P (2009) Top Catal 52:278
Al Badran F, Awdry S, Kolaczkowski ST (2013) Catal Today 216:229
Osako T, Torii K, Uozumi Y (2015) RSC Adv 5:2647
Wang NW, Matsumoto T, Ueno M, Miyamura H, Kobayashi S (2009) Angew Chem Int Ed 48:4744
Kaizuka K, Lee KY, Miyamura H, Kobayashi S (2012) J Flow Chem 2:1
Zope BN, Davis RJ (2009) Top Catal 52:269
Zope BN, Davis SE, Davis RJ (2012) Top Catal 55:24
Pollington SD, Enache DI, Landon P, Meenakshisundaram S, Dimitratos N, Wagland A, Hutchings GJ, Stitt EH (2009) Catal Today 145:169
Cao EH, Sankar M, Firth S, Lam KF, Bethell D, Knight DK, Hutchings GJ, McMillan PF, Gavriilidis A (2011) Chem Eng J 167:734
Asao N, Hatakeyama N, Menggenbateer, Minato T, Ito E, Hara M, Kim Y, Yamamoto Y, Chen MW, Zhang W, Inouei A (2012) Chem Commun 48:4540
Heidkamp K, Aytemir M, Vorlop KD, Prusse U (2013) Catal Sci Technol 3:2984
Wu GW, Constantinou A, Cao EH, Kuhn S, Morad M, Sankar M, Bethell D, Hutchings GJ, Gavriilidis A (2015) Ind Eng Chem Res 54:4183
Chaudhuri SR, Hartwig J, Kupracz L, Kodanek T, Wegner J, Kirschning A (2014) Adv Synth Catal 356:3530
Aellig C, Girard C, Hermans I (2011) Angew Chem Int Ed 50:12355
Aellig C, Scholz D, Hermans I (2012) ChemSusChem 5:1732
Aellig C, Scholz D, Conrad S, Hermans I (2013) Green Chem 15:1975
Leitner W (2002) Acc Chem Res 35:746
Rayner CM (2007) Org Process Res Dev 11:121
Han X, Poliakoff M (2012) Chem Soc Rev 41:1428
Jenzer G, Sueur D, Mallat T, Baiker A (2000) Chem Commun 2000:2247
Jenzer G, Schneider MS, Wandeler R, Mallat T, Baiker A (2001) J Catal 199:141
Jenzer G, Mallat T, Baiker A (2001) Catal Lett 73:5
Grunwaldt JD, Caravati M, Ramin M, Baiker A (2003) Catal Lett 90:221
Caravati M, Grunwaldt JD, Baiker A (2004) Catal Today 91–2:1
Caravati M, Grunwaldt JD, Baiker A (2005) Phys Chem Chem Phys 7:278
Burgener M, Tyszewski T, Ferri D, Mallat T, Baiker A (2006) Appl Catal A-Gen 299:66
Caravati M, Grunwaldt JD, Baiker A (2006) Appl Catal A-Gen 298:50
Grunwaldt JD, Baiker A (2005) Phys Chem Chem Phys 7:3526
Caravati M, Meier DM, Grunwaldt JD, Baiker A (2006) J Catal 240:126
Caravati M, Grunwaldt JD, Baliker A (2007) Catal Today 126:27
Grunwaldt JD, Caravati M, Baiker A (2006) J Phys Chem B 110:9916
Beier MJ, Grunwaldt JD, Tsivintzelis I, Jensen AD, Kontogeorgis GM, Baiker A (2012) J Supercrit Fluid 63:199
Chapman AO, Akien GR, Arrowsmith NJ, Licence P, Poliakoff M (2010) Green Chem 12:310
Keresszegi C, Grunwaldt JD, Mallat T, Baiker A (2003) Chem Commun 2304
Grunwaldt JD, Keresszegi C, Mallat T, Baiker A (2003) J Catal 213:291
Grunwaldt JD, Caravati M, Baiker A (2006) J Phys Chem B 110:25586
Hou Z, Theyssen N, Brinkmann A, Leitner W (2005) Angew Chem Int Ed 44:1346
Hou ZS, Theyssen N, Leitner W (2007) Green Chem 9:127
Hou Z, Theyssen N, Brinkmann A, Klementiev KV, Grunert W, Buhl M, Schmidt W, Spliethoff B, Tesche B, Weidenthaler C, Leitner W (2008) J Catal 258:315
Stahl SS (2005) Science 309:1824
Stahl SS (2004) Angew Chem Int Ed 43:3400
Steinhoff BA, Stahl SS (2006) J Am Chem Soc 128:4348
Ye XA, Johnson MD, Diao TN, Yates MH, Stahl SS (2010) Green Chem 12:1180
Greene JF, Hoover JM, Mannel DS, Root TW, Stahl SS (2013) Org Process Res Dev 17:1247
Vanoye L, Pablos M, de Bellefon C, Favre-Reguillon A (2015) Adv Synth Catal 357:739
Greene JF, Preger Y, Stahl SS, Root TW (2015) Org Process Res Dev doi:10.1021/acs.oprd.5b00125
Franke R, Selent D, Borner A (2012) Chem Rev 112:5675
Röhrscheid F (2000) Carboxylic acids, aromatic Ullmann's encyclopedia of industrial chemistry. Wiley-VCH, Weinheim, Germany
Haverkamp V, Hessel V, Liauw MA, Lowe H, Menges MG (2007) Ind Eng Chem Res 46:8558
Liu XY, Unal B, Jensen KF (2012) Catal Sci Technol 2:2134
Vanoye L, Aloui A, Pablos M, Philippe R, Percheron A, Favre-Reguillon A, de Bellefont C (2013) Org Lett 15:5978
Vanoye L, Pablos M, Smith N, de Bellefon C, Favre-Reguillon A (2014) RSC Adv 4:57159
Seechurn CCCJ, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 51:5062
Cantillo D, Kappe CO (2014) ChemCatChem 6:3286
Noel T, Buchwald SL (2011) Chem Soc Rev 40:5010
Karimi B, Behzadnia H, Elhamifar D, Akhavan PF, Esfahani FK, Zamani A (2010) Synthesis 2010:1399
Gligorich KM, Sigman MS (2009) Chem Commun 3854
Park CP, Kim DP (2010) J Am Chem Soc 132:10102
Park JH, Park CY, Kim MJ, Kim MU, Kim YJ, Kim GH, Park CP (2015) Org Process Res Dev. doi:10.1021/acs.oprd.5b00077
Rudzinski DM, Leadbeater NE (2013) Green Process Synth 2:323
Gemoets HPL, Hessel V, Noel T (2014) Org Lett 16:5800
Petersen TP, Polyzos A, O'Brien M, Ulven T, Baxendale IR, Ley SV (2012) ChemSusChem 5:274
Brzozowski M, Forni JA, Savage GP, Polyzos A (2015) Chem Commun 51:334
Ratnikov MO, Xu XF, Doyle MP (2013) J Am Chem Soc 135:9475
Goebel MT, Marvel CS (1933) J Am Chem Soc 55:1693
Porter CW, Steel C (1920) J Am Chem Soc 42:2650
Russell GA, Bridger RF (1963) J Am Chem Soc 85:3765
He Z, Jamison TF (2014) Angew Chem Int Ed 53:3353
Schmidt RJ (2005) Appl Catal A-Gen 280:89
Fraga-Dubreuil J, Garcia-Serna J, Garcia-Verdugo E, Dudd LM, Aird GR, Thomas WB, Poliakoff M (2006) J Supercrit Fluid 39:220
Thomas ML, Fraga-Dubreuil J, Coote AS, Poliakoff M (2008) Green Chem 10:197
Hunig S, Muller HR, Thier W (1965) Angew Chem Int Ed 4:271
Pasto DJ, Taylor RT (1991) Org React 40:91
Pieber B, Martinez ST, Cantillo D, Kappe CO (2013) Angew Chem Int Ed 52:10241
Pieber B, Glasnov T, Kappe CO (2015) Chem Eur J 21:4368
Feth MP, Rossen K, Burgard A (2013) Org Process Res Dev 17:282
Gilmore K, Seeberger PH (2014) Chem Rec 14:410
Su YH, Straathof NJW, Hessel V, Noel T (2014) Chem Eur J 20:10562
Talla A, Driessen B, Straathof NJW, Milroy L-G, Brunsveld L, Hessel V, Noël T (2015) Adv Synth Catal. doi:10.1002/adsc.201401010
Su Y, Hessel V, Noël T (2015) AIChE 61:2215
Zou YQ, Chen JR, Liu XP, Lu LQ, Davis RL, Jorgensen KA, Xiao WJ (2012) Angew Chem Int Ed 51:784
Penders IGTM, Amara Z, Horvath R, Rossen K, Poliakoff M, George MW (2015) RSC Adv 5:6501
Ogilby PR (2010) Chem Soc Rev 39:3181
Wootton RCR, Fortt R, de Mello AJ (2002) Org Process Res Dev 6:187
Loponov KN, Lopes J, Barlog M, Astrova EV, Malkov AV, Lapkin AA (2014) Org Process Res Dev 18:1443
Jahnisch K, Dingerdissen U (2005) Chem Eng Technol 28:426
Park CP, Maurya RA, Lee JH, Kim DP (2011) Lab Chip 11:1941
Maurya RA, Park CP, Kim DP (2011) Beilstein J Org Chem 7:1158
Levesque F, Seeberger PH (2011) Org Lett 13:5008
Heugebaert TSA, Stevens CV, Kappe CO (2015) ChemSusChem 8:1648
Elvira KS, Wootton RCR, Reis NM, Mackley MR, DeMello AJ (2013) ACS Sustain Chem Eng 1:209
Park CY, Kim YJ, Lim HJ, Park JH, Kim MJ, Seo SW, Park CP (2015) RSC Adv 5:4233
Lumley EK, Dyer CE, Pamme N, Boyle RW (2012) Org Lett 14:5724
Ushakov DB, Gilmore K, Kopetzki D, McQuade DT, Seeberger PH (2014) Angew Chem Int Ed 53:557
Ushakov DB, Gilmore K, Seeberger PH (2014) Chem Commun 50:12649
Ushakov DB, Plutschack MB, Gilmore K, Seeberger PH (2015) Chem Eur J 21:6528
Vukelic S, Ushakov DB, Gilmore K, Koksch B, Seeberger PH (2015) Eur J Org Chem 2015:3036
Levesque F, Seeberger PH (2012) Angew Chem Int Ed 51:1706
Kopetzki D, Levesque F, Seeberger PH (2013) Chem Eur J 19:5450
Gilmore K, Kopetzki D, Lee JW, Horvath Z, McQuade DT, Seidel-Morgenstern A, Seeberger PH (2014) Chem Commun 50:12652
Bourne RA, Han X, Chapman AO, Arrowsmith NJ, Kawanami H, Poliakoff M, George MW (2008) Chem Commun 2008:4457
Bourne RA, Han X, Poliakoff M, George MW (2009) Angew Chem Int Ed 48:5322
Han X, Bourne RA, Poliakoff M, George MW (2009) Green Chem 11:1787
Han X, Bourne RA, Poliakoff M, George MW (2011) Chem Sci 2:1059
Hall JFB, Han X, Poliakoff M, Bourne RA, George MW (2012) Chem Commun 48:3073
Hall JFB, Bourne RA, Han X, Earley JH, Poliakoff M, George MW (2013) Green Chem 15:177
Amara Z, Bellamy JFB, Horvath R, Miller SJ, Beeby A, Burgard A, Rossen K, Poliakoff M, George MW (2015) Nat Chem 7:489
Acknowledgments
Research on continuous flow chemistry in our laboratories over the past decade has been generously supported by the Christian Doppler Research Association (CDG) and a variety of industrial partners including Lonza, DPx, Microinnova, ThalesNano, Anton Paar, Eli Lilly, Bayer Pharma, BASF, and Clariant.
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Pieber, B., Kappe, C.O. (2015). Aerobic Oxidations in Continuous Flow. In: Noël, T. (eds) Organometallic Flow Chemistry. Topics in Organometallic Chemistry, vol 57. Springer, Cham. https://doi.org/10.1007/3418_2015_133
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