Abstract
This chapter presents a brief overview regarding the use of flow microreactors for the preparation and reactions of organometallic species, with special emphasis on the synthetic transformations using highly reactive species such as organolithiums and organomagnesiums that are difficult or impossible to achieve using conventional batch reactors.
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References
Hessel V, Hardt S, Löwe H (2004) Chemical micro process engineering. Wiley-VCH, Weinheim
Wirth T (2008) Microreactors in organic synthesis and catalysis. Wiley-VCH, Weinheim
Hessel V, Renken A, Schouten JC, Yoshida J (2009) Micro process engineering. Wiley-VCH, Weinheim
Watts P, Wiles C (2011) Micro reaction technology in organic synthesis. CRC, New York
Baldwin JE, Williams RM (2002) Organolithiums: selectivity for synthesis. Pregamon, Amsterdam
Hikage S, Yoshida J. JP 2003-337787, JP 4639042
Schwalbe T, Autze V, Hohmann M, Stirner W (2004) Org Process Res Dev 8:440
Zhang X, Stefanick S, Villani FJ (2004) Org Process Res Dev 8:455
Nagaki A, Tomida Y, Usutani H, Kim H, Takabayashi N, Nokami T, Okamoto H, Yoshida J (2007) Chem Asian J 2:1513
Aoki N, Kitajima R, Itoh C, Mae K (2008) Chem Eng Technol 31:1140–1145
Usutani H, Tomida Y, Nagaki A, Okamoto H, Nokami T, Yoshida J (2007) J Am Chem Soc 129:3046
Chen LS, Chen GJ, Tamborski C (1980) J Organomet Chem 193:283
Nagaki A, Imai K, Kim H, Yoshida J (2011) RSC Adv 1:758
Choe J, Seo JH, Kwon Y, Song KH (2008) Chem Eng J 135S:S17
Nagaki A, Yamada S, Doi M, Tomida Y, Takabayashi N, Yoshida J (2011) Green Chem 13:1110
Nagaki A, Yamada D, Yamada S, Doi M, Tomida Y, Takabayashi N, Yoshida J (2013) Aust J Chem 66:199
Goto S, Velder J, Sheikh SE, Sakamoto Y, Mitani M, Elmas S, Adler A, Becker A, Neudörfl JM, Lex J, Schmalz HG (2008) Synlett 9:1361
Nagaki A, Uesugi Y, Kim H, Yoshida J (2013) Chem Asian J 8:705
Pieber B, Glasnov T, Kappe CO (2014) RSC Adv 4:13430–13433
Wu J, Yang X, He Z, Mao X, Hatton TA, Jamison TF (2014) Angew Chem Int Ed 53:8416–8420
Knochel P (2005) Handbook of functionalized organometallics. Wiley-VCH, Weinheim
Parham WE, Bradsher CK (1982) Acc Chem Res 15:300
Sapountzis I, Knochel P (2002) Angew Chem Int Ed 41:1610
Sapountzis I, Dube H, Lewis R, Gommermann N, Knochel P (2005) J Org Chem 70:2445
Nagaki A, Kim H, Yoshida J (2009) Angew Chem Int Ed 48:8063
Nagaki A, Kim H, Yoshida J (2008) Angew Chem Int Ed 47:7833
Nagaki A, Kim H, Moriwaki Y, Matsuo C, Yoshida J (2010) Chem Eur J 16:11167
Nagaki A, Kim H, Matsuo C, Yoshida J (2010) Org Biomol Chem 8:1212
Kim H, Nagaki A, Yoshida J (2011) Nat Commun 2:264
Kim H, Lee H, Kim D (2015) Angew Chem Int Ed 54:1877
Nagaki A, Takahashi Y, Yoshida J (2014) Chem Eur J 20:7931–7934
Brown HC, Cole TE (1983) Organometallics 2:1316
Ishiyama T, Miyaura N (2000) J Organomet Chem 611:392
Mo F, Jiang Y, Qiu D, Zhang Y, Wang J (2010) Angew Chem Int Ed 49:1846
Browne DL, Baumann M, Harji BH, Baxendale IR, Ley SV (2011) Org Lett 13:3312
Newby JA, Huck L, Blaylock DW, Witt PM, Ley SV, Browne DJ (2014) Chem Eur J 20:263–271
Shu W, Pellegatti L, Oberli MA, Buchwald SL (2011) Angew Chem Int Ed 50:10665
Nagaki A, Moriwaki Y, Yoshida J (2012) Chem Commun 48:11211
Neumann H, Seebach D (1976) Tetrahedron Lett 17:4839
Nagaki A, Takahashi Y, Yamada S, Matsuo C, Haraki S, Moriwaki Y, Kim S, Yoshida J (2012) J Flow Chem 2:70
Nagaki A, Matsuo C, Kim S, Saito K, Miyazaki A, Yoshida J (2012) Angew Chem Int Ed 51:3245
Nagaki A, Takahashi Y, Henseler A, Matsuo C, Yoshida J (2015) Chem Lett 44:214–216
Drakesmith FG, Stewart OJ, Tarrant P (1968) J Org Chem 33:280
Nadano R, Fuchibe K, Ikeda M, Takahashi H, Ichikawa J (2010) Chem Asian J 5:1875
Nagaki A, Tokuoka S, Yoshida J (2014) Chem Commun 50:15079
Tomida Y, Nagaki A, Yoshida J (2009) Org Lett 11:3614
Chinkov N, Chechik H, Majumdar S, Liard A, Marek I (2002) Synthesis 2473
Nagaki A, Tsuchihashi Y, Haraki S, Yoshida J (2015) Org Biomol Chem 13:7140–7145
Kupracz L, Kirschning A (2013) Adv Synth Catal 355:3375–3380
Fukuyama T, Totoki T, Ryu I (2014) Org Lett 16:5632–5635
Uneyama K, Katagiri T, Amii H (2008) Acc Chem Res 41:817
Nagaki A, Tokuoka S, Yamada S, Tomida Y, Oshiro K, Amii H, Yoshida J (2011) Org Biomol Chem 9:7559
Ushiogi Y, Hase T, Iinuma Y, Takata A, Yoshida J (2007) Chem Commun 2947
Asai T, Takata A, Nagaki A, Yoshida J (2012) ChemSusChem 5:339
Degennaro L, Fanelli F, Giovine A, Luisi R (2015) Adv Synth Catal 357:21–27
Satoh T (1996) Chem Rev 96:3303
Capriati V, Florio S, Luisi R (2008) Chem Rev 108:1918
Nagaki A, Takizawa E, Yoshida J (2009) J Am Chem Soc 131:1654
Nagaki A, Takizawa E, Yoshida J (2009) Chem Lett 38:486
Nagaki A, Takizawa E, Yoshida J (2010) Chem Eur J 16:14149
Nagaki A, Takizawa E, Yoshida J (2009) Chem Lett 38:1060
Takizawa E, Nagaki A, Yoshida J (2012) Tetrahedron Lett 53:1397
Giovine A, Musio B, Degennaro L, Falcicchio A, Nagaki A, Yoshida J, Luisi R (2013) Chem Eur J 19:1872
Umezu S, Yoshiiwa T, Tokeshi M, Shindo M (2014) Tetrahedron Lett 55:1822–1825
Yoshiiwa T, Umezu S, Tokeshi M, Baba Y, Shindo M (2014) J Flow Chem 4:180–184
Asai T, Takata A, Ushiogi Y, Iinuma Y, Nagaki A, Yoshida J (2011) Chem Lett 40:393
Tomida Y, Nagaki A, Yoshida J (2011) J Am Chem Soc 133:3744
Kagan HB (1995) Recl Travl Chim Pays-Bas 114:203
Rys P (1976) Acc Chem Res 9:345
Suga S, Nagaki A, Yoshida J (2003) Chem Commun 354
Nagaki A, Togai M, Suga S, Aoki N, Mae K, Yoshida J (2005) J Am Chem Soc 127:11666
Suga S, Nagaki A, Tsutsui Y, Yoshida J (2003) Org Lett 5:945
Suga S, Tsutsui Y, Nagaki A, Yoshida J (2005) Bull Chem Soc Jpn 78:1206
Yoshida J, Nagaki A, Iwasaki T, Suga S (2005) Chem Eng Technol 28:259
Beak P, Liu C (1994) Tetrahedron Lett 20:5999
Klis T, Servatowski J (2007) Tetrahedron Lett 48:1169
Nagaki A, Takabayashi N, Tomida Y, Yoshida J (2008) Org Lett 10:3937
Nagaki A, Takabayashi N, Tomida Y, Yoshida J (2009) Beilstein J Org Chem 5(16)
Ishigaki Y, Suzuki T, Nishida J, Nagaki A, Takabayashi N, Kawai H, Fujiwara K, Yoshida J (2011) Materials 4:1906
Suzuki T, Uchimura Y, Ishigaki Y, Takeda T, Katoono R, Kawai H, Fujiwara K, Nagaki A, Yoshida J (2012) Chem Lett 41:541
Suzuki T, Uchimura Y, Nagasawa F, Takeda T, Kawai H, Katoono R, Fujiwara K, Murakoshi K, Fukushima T, Nagaki A, Yoshida J (2014) Chem Lett 43:86–88
Nagaki A, Ichinari D, Yoshida J (2013) Chem Commun 49:3242–3244
Nagaki A, Imai K, Ishiuchi S, Yoshida J (2015) Angew Chem Int Ed 54:1914–1918
Yoshida J, Saito K, Nokami T, Nagaki A (2011) Synlett 1189
Suga S, Yamada D, Yoshida J (2010) Chem Lett 404
Nagaki A, Ichinari D, Yoshida J (2014) J Am Chem Soc 136:12245–12248
Murahashi SI, Yamamura M, Yanagisawa K, Mita N, Kondo K (1979) J Org Chem 44:2408
Nagaki A, Kenmoku A, Moriwaki Y, Hayashi A, Yoshida J (2010) Angew Chem Int Ed 49:7543
Nagaki A, Moriwaki Y, Haraki S, Kenmoku A, Hayashi A, Yoshida J (2012) Chem Asian J 7:1061
Nagaki A, Uesugi Y, Tomida Y, Yoshida J (2011) Beilstein J Org Chem 7:1064
Shu W, Buchwald SL (2012) Angew Chem Int Ed 51:5355
Wakami H, Yoshida J (2005) Org Process Res Dev 9:787–791
Brodmann T, Koos P, Metzger A, Knochel P, Ley SV (2012) Org Process Res Dev 16:1102–1113
Petersen TP, Becker MR, Knochel P (2014) Angew Chem Int Ed 53:7933–7937
Tricotet T, O’Shea DF (2010) Chem Eur J 16:6678–6686
Riva E, Gagliardi S, Martinelli M, Passarella D, Vigo D, Rencurosi A (2010) Tetrahedron 66:3242–3247
Mateos C, Rincon JA, Villanueva J (2013) Tetrahedron Lett 54:2226–2230
Taghavi-Moghadam S, Kleemann A, Golbig KG (2001) Org Process Res Dev 5:652–658
Golbis K, Hohmann M, Kursawe A, Schwalbe T (2004) Chem Ing Tech 76(5):598–603
Roberge DM, Bieler N, Mathier M, Eyholzer M, Zimmermann B, Barthe P, Guermeur C, Lobet O, Moreno M, Woehl P (2008) Chem Eng Technol 31:1155–1161
Polyzos A, O’Brien M, Petersen TP, Baxendale IR, Ley SV (2011) Angew Chem Int Ed 50:1190–1193
Deng Q, Shen R, Zhao Z, Yan M, Zhang L (2015) Chem Eng J 262:1168–1174
He Z, Jamison TF (2014) Angew Chem Int Ed 53:3353–3357
Seyler H, Subbiah J, Jones DJ, Holmes AB, Wong WWH (2013) Beilstein J Org Chem 9:1492–1500
Styring P, Parracho AIR (2009) Beilstein J Org Chem 5(29):1–10
Hessel V, Hofmann C, Löwe H, Meudt A, Scherer S, Schönfeld F, Werner B (2004) Org Process Res Dev 8:511–523
Deng Q, Shen R, Ding R, Zhang L (2014) Adv Synth Catal 356:2931–2936
Battilocchio C, Baxendale IR, Biava M, Kitching MO, Ley SV (2012) Org Process Res Dev 16:798–810
Hamlin TA, Lazarus GML, Kelly CB, Leadbeater NE (2014) Org Process Res Dev 18:1253–1258
Szwarc M (1956) Nature 178:1168
Nagaki A, Tomida Y, Yoshida J (2008) Macromolecules 41:6322
Wurm F, Wilms D, Klos J, Löwe H, Frey H (2008) Macromol Chem Phys 209:1106
Natalello A, Morsbach J, Friedel A, Alkan A, Tonhauser C, Müller AHE, Frey H (2014) Org Process Res Dev 18:1408–1412
Tonhauser C, Wilms D, Wurm F, Berger-Nicoletti E, Maskos M, Löwe H, Frey H (2010) Macromolecules 43:5582
Nagaki A, Kawamura K, Suga S, Ando T, Sawamoto M, Yoshida J (2005) J Am Chem Soc 126:14703
Yoshida J, Nagaki A, Iwasaki T, Suga S (2005) Chem Eng Technol 3:259
Iida K, Chastek TQ, Beers KL, Cavicchi KA, Chun J, Fasolka MJ (2009) Lab Chip 9:339
Nagaki A, Tomida Y, Miyazaki A, Yoshida J (2009) Macromolecules 42:4384
Nagaki A, Miyazaki A, Tomida Y, Yoshida J (2011) Chem Eng J 167:548
Nagaki A, Akahori K, Takahashi Y, Yoshida J (2014) J Flow Chem 4:168–172
Nagaki A, Takahashi S, Akahori K, Yoshida J (2012) Macromol React Eng 6:467
Nagaki A, Miyazaki A, Yoshida J (2010) Macromolecules 43:8424
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Nagaki, A., Yoshida, JI. (2015). Preparation and Use of Organolithium and Organomagnesium Species in Flow. In: Noël, T. (eds) Organometallic Flow Chemistry. Topics in Organometallic Chemistry, vol 57. Springer, Cham. https://doi.org/10.1007/3418_2015_154
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DOI: https://doi.org/10.1007/3418_2015_154
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