Organic Process Research & Development
Article
analytical/. (q) Wilson, N.; Sarko, C.; Roth, G. Org. Process Res. Dev.
2004, 8, 535. (r) Paulus, R. M.; Erdmenger, T.; Becer, C. R.;
Hoogenboom, R.; Schubert, U. S. Macromol. Rapid Commun. 2007, 28,
484. (s) Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer,
G. K. Chem.Eur. J. 2006, 12, 4407. (t) Murphy, E. R.; Martinelli, J.
R.; Zaborenko, N.; Buchwald, S. L.; Jensen, K. V. Angew. Chem., Int.
Ed. 2007, 46, 1734.
ABBREVIATIONS
■
DMI, 1,3-dimethyl-2-imidazolidinone; DMA, dimethylaceta-
mide; MACOS, microwave-assisted continuous flow for organic
synthesis.
REFERENCES
■
(1) Kappe, C. O. Angew. Chem. 2004, 116, 6408; Angew. Chem., Int.
Ed. 2004, 43, 6250.
(2) Microwaves in Organic Synthesis, 1st ed.; Loupy, A., Ed.; Wiley-
VCH: Weinheim, Germany, 2002.
(3) Hoodgenboom, R.; Paulas, R. M.; Pilotti, Å; Schubert, U. S.
Macromol. Rapid Commun. 2006, 27, 1556.
(4) Loupy, A.; Maurel, F.; Sabatie-Gogova, A. Tetrahedron 2004, 60,
1683.
(5) Hoz, D. A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34,
164.
(6) Singh, B. K.; Kaval, N.; Tomar, S.; Van der Eycken, E.; Parmar, V.
S. Org. Process Res. Dev. 2008, 12, 468.
(7) Wiles, C.; Watts, P. Beilstein J. Org. Chem. 2011, 7, 1160.
(23) Kawanami, H.; Matsushima, K.; Sato, M.; Ikushima, Y. Angew.
Chem., Int. Ed. 2007, 46, 5129.
(24) Noel, T.; Naber, J. R.; Hartman, R. L.; McMullen, J. P.; Jensen,
̈
K.; Buchwald, S. L. Chem. Sci. 2011, 2, 288.
(25) Kremsner, J.; Kappe, C. O. J. Org. Chem. 2006, 71, 4651.
(26) Obermayer, D.; Gutmann, B.; Kappe, C. O. Angew. Chem. 2009,
121, 8471; Angew. Chem., Int. Ed. 2009, 48, 8321.
(27) Damm, M.; Kappe, C. O. Mol. Diversity 2009, 13, 529.
(28) See Figures S1 and S2 in the Supporting Information for
photographs of the modified Biotage microwave reactor.
(29) See Figure S3 in the Supporting Information for a blow-up of
the PCD.
(30) While not the focus of this manuscript, the reactor is set up with
in-line continuous quality control analysis by GC/MS. A schematic
(Figure S4) and photograph (Figure S5) of the whole reactor set up,
including GC/MS analysis, have been included in the Supporting
Information. Sample can be withdrawn constantly from the high-
pressure reactor for in-line analysis using the unique design with no
change in the pressure of the system.
(31) The thermal conductivity of SiC is substantially greater than that
of glass at 300 K. (For representative thermal conductivities of various
forms of SiC, see: Thuault, A.; Savary, E.; Bazin, J.; Marinel, S. J. Mater.
Process. Technol. 2013, 214, 470. Harris, G. L. Thermal Conductivity of
SiC. In Properties of Silicon Carbide; Harris, G. L., Ed.; EMIS
Datareviews Series, Vol. 13; IET: London, 1995; pp 5−6.)
Consequently, heat transfer was assumed to be complete and
instantaneous. This hypothesis was later supported experimentally. A
target temperature of 100 °C (i.e., 373 K) was recorded for deionised
water when an external IR camera (calibrated) was mounted at the exit
port of a 25 cm long reactor cell even at a high flow rate (300 μL/
min).
(8) De La Hoz, A.; Alcaz
́
ar, J.; Carillo, J.; Herrero, M. A.; Munoz, J.
ar, A.; Diaz-Ortiz, A. Reproducibility and
̃
D. M.; Prieto, P.; De Coz
́
Scalability of Microwave-Assisted Reactions. In Microwave Heating;
Chandra, U., Ed.; InTech: Rijeka, Croatia, 2011; pp 137−162;
(9) KaMa, H.; Bo, L. Sci. China, Ser. E: Technol. Sci. 2009, 2, 491.
(10) Johnson, M. D.; May, S. A.; Calvin, J. R.; Remacle, J.; Stout, J.
R.; Diseroad, W. D.; Zaborenko, N.; Haeberle, B. D.; Sun, W.-M.;
Miller, M. T.; Brennan, J. Org. Process Res. Dev. 2012, 16, 1017.
(11) Comer, E.; Organ, M. G. J. Am. Chem. Soc. 2005, 127, 8160.
(12) Zang, Q.; Javed, S.; Hill, D.; Ullah, F.; Bi, D.; Porubsky, P.;
Neuenswander, B.; Lushington, G. H.; Santini, C.; Organ, M. G.;
Hanson, P. R. ACS Comb. Sci. 2012, 14, 456.
(13) Zang, Q.; Javed, S.; Porubsky, P.; Ullah, F.; Neuenswander, B.;
Lushington, G. H.; Basha, F. Z.; Organ, M. G.; Hanson, P. R. ACS
Comb. Sci. 2012, 14, 211.
(14) Achanta, S.; Liautard, V.; Paugh, R.; Organ, M. G. Chem.Eur.
J. 2010, 16, 12797.
(15) Shore, G.; Morin, S.; Mallik, D.; Organ, M. G. Chem.Eur. J.
2008, 14, 1351.
(16) Shore, G.; Organ, M. G. Gold Bull. 2010, 43, 105.
(17) Organ, M. G.; Shore, G.; Tsimerman, M. Beilstein J. Org. Chem.
2009, 5, No. 35.
(32) Razzaq, T.; Glasnov, T. N.; Kappe, C. O. Chem. Eng. Technol.
2009, 32, 1702.
(33) Razzaq, T.; Glasnov, T. N.; Kappe, C. O. Eur. J. Org. Chem.
2009, 1321.
(34) Damm, M.; Glasnov, T.; Kappe, C. O. Org. Process Res. Dev.
2010, 14, 215.
(35) Morschhauser, R.; Krull, M.; Keyser, C.; Boberski, C.; Bierbaum,
R.; Puschner, P. A.; Glasnov, T. N.; Kappe, C. O. Green Process. Synth.
2012, 1, 281.
(18) Shore, G.; Yoo, W. J.; Li, C. J.; Organ, M. G. Chem.Eur. J.
2010, 16, 126.
(19) Painter, T. O.; Thornton, P. D.; Orestano, M.; Santini, C.;
Organ, M. G.; Aube,
́
J. Chem.Eur. J. 2011, 17, 9595.
(20) Ullah, F.; Zang, Q.; Javed, S.; Porubsky, P.; Neuenswander, B.;
Lushington, G. H.; Bash, F. Z.; Hanson, P. R.; Organ, M. G. Synthesis
2012, 44, 2547.
(21) Shore, G.; Organ, M. G. Chem. Commun. 2008, 838−840.
(22) (a) Bondioli, F.; Corradi, A. B.; Ferrari, A. M.; Leonelli, C. J. Am.
Ceram. Soc. 2008, 91, 3746. (b) Corradi, A. B.; Bondioli, F.; Ferrari, A.
M.; Focher, B.; Leonelli, C. Powder Technol. 2006, 167, 45. (c) Braun,
I.; Schulz-Ekloff, G.; Wohrle, D.; Lautenschlager, W. Microporous
̈
̈
Mesoporous Mater. 1998, 23, 79. (d) Dressen, M. H. C. L.; van de
Kruijs, B. H. P.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Org.
Process Res. Dev. 2010, 14, 351. (e) Cablewski, T.; Faux, A. F.; Strauss,
C. R. J. Org. Chem. 1994, 59, 3408. (f) Chemat, F.; Poux, M.; Martino,
J.; Berlan, J. Chem. Eng. Technol. 1996, 19, 420. (g) Benali, O.; Deal,
M.; Farrant, E.; Tapolczay, D.; Wheeler, R. Org. Process Res. Dev. 2008,
12, 1007. (h) Glasnov, T. N.; Vugts, D. J.; Koningstein, M. M.; Desai,
B.; Fabian, W. M. F.; Orru, R. V. A.; Kappe, C. O. QSAR Comb. Sci.
2006, 25, 509. (i) Groisman, Y.; Gedanken, A. J. Phys. Chem. C 2008,
112, 8802. (j) He, P.; Haswell, S. J.; Fletcher, P. D. I. Appl. Catal., A
2004, 274, 111. (k) He, P.; Haswell, S. J.; Fletcher, P. D. I. Sens.
Actuators, B 2005, 105, 516. (l) Marquie, J.; Salmoria, G.; Poux, M.;
Laporterie, A.; Dubac, J.; Roques, N. Ind. Eng. Chem. Res. 2001, 40,
4485. (m) Pipus, G.; Plazl, I.; Koloini, T. Chem. Eng. J. 2000, 76, 239.
E
dx.doi.org/10.1021/op400026g | Org. Process Res. Dev. XXXX, XXX, XXX−XXX