Synlett 2014; 25(15): 2087-2092
DOI: 10.1055/s-0034-1378244
synpacts
© Georg Thieme Verlag Stuttgart · New York

Microflow Technology: Another Solution for the Site-Selective Modification of Multifunctionalized Molecules

Shinichiro Fuse*
a   Department of Applied Chemistry, Tokyo Institute of Technology 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552, Japan   Fax: +81(3)57342884   Email: sfuse@apc.titech.ac.jp
,
Yuto Mifune
a   Department of Applied Chemistry, Tokyo Institute of Technology 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552, Japan   Fax: +81(3)57342884   Email: sfuse@apc.titech.ac.jp
,
Nobutake Tanabe
a   Department of Applied Chemistry, Tokyo Institute of Technology 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552, Japan   Fax: +81(3)57342884   Email: sfuse@apc.titech.ac.jp
,
Takashi Takahashi
b   Yokohama College of Pharmacy 601, Matana-cho, Totsuka-ku, Yokohama-shi 245-0066, Japan
› Author Affiliations
Further Information

Publication History

Received: 11 April 2014

Accepted after revision: 05 May 2014

Publication Date:
24 June 2014 (online)


Abstract

The synthesis of multifunctionalized organic molecules is challenging because multiple functional groups frequently causes unexpected side reactions. The recent emergence of microflow technology has offered a new solution to this problem. Herein, we wish to describe our recent achievements in the microflow synthesis of multifunctionalized molecules such as vitamin D and peptides.

 
  • References

    • 2a Yoshida J.-i, Nagaki A, Yamada T. Chem. Eur. J. 2008; 14: 7450
    • 2b Yoshida J.-i. Flash Chemistry – Fast Organic Synthesis in Micro Systems. Wiley-Blackwell; Hoboken: 2008
    • 2c Fukuyama T, Rahman T, Sato M, Ryu I. Synlett 2008; 151
    • 2d Wiles C, Watts P. Eur. J. Org. Chem. 2008; 1655
    • 2e Handbook of Microreactors. Hessel V, Schouten JC, Renken A, Wang Y, Yoshida J.-i. Wiley-VCH; Weinheim: 2009
    • 2f Yoshida J.-i. Chem. Rec. 2010; 10: 332
    • 2g Chemical Reactions and Processes under Flow Conditions. Luis SV, Carcia-Verdugo E. Royal Society of Chemistry; Cambridge: 2010
    • 2h McMullen JP, Jensen KF. Annu. Rev. Anal. Chem. 2010; 3: 19
    • 2i Baumann M, Baxendale IR, Ley SV. Mol. Diversity 2011; 15: 613
    • 2j Oelgemöller M, Shvydkiv O. Molecules 2011; 16: 7522
    • 2k Yoshida J.-i, Kim H, Nagaki A. ChemSusChem 2011; 4: 331
    • 2l Wegner J, Ceylan S, Kirschning A. Chem. Commun. 2011; 47: 4583
    • 2m Wegner J, Ceylan S, Kirschning A. Adv. Synth. Catal. 2012; 354: 17
    • 2n Knowles JP, Elliott LD, Booker-Milburn KI. Beilstein J. Org. Chem. 2012; 8: 2025
    • 2o Baxendale IR, Hornung C, Ley SV, de Mata Muñoz Molina J, Wikström A. Aust. J. Chem. 2013; 66: 131
    • 2p Oelgemöller M. Chem. Eng. Technol. 2012; 35: 1144
    • 2q Anderson NG. Org. Process Res. Dev. 2012; 16: 852
    • 2r Microreactors in Organic Chemistry and Catalysis. Wirth T. Wiley-VCH; Weinheim: 2013
    • 2s Protasova LN, Bulut M, Ormerod D, Buekenhoudt A, Berton J, Stevens CV. Org. Process Res. Dev. 2013; 17: 760
    • 2t Hessel V, Kralisch D, Kockmann N, Noël T, Wang Q. ChemSusChem 2013; 6: 746
    • 2u Pastre JC, Browne DL, Ley SV. Chem. Soc. Rev. 2013; 42: 8849
  • 3 Kim H, Nagaki A, Yoshida J.-i. Nat. Commun. 2011; 2: 264
  • 4 Fuse S. J. Synth. Org. Chem., Jpn. 2012; 70: 177
  • 5 Sustainable Industrial Chemistry . Cavani F, Centi G, Perathoner S, Trifiro F. Wiley-VCH; Weinheim: 2009
    • 6a Fuse S, Hanochi M, Doi T, Takahashi T. Tetrahedron Lett. 2004; 45: 1961
    • 6b Doi T, Fuse S, Miyamoto S, Nakai K, Sasuga D, Takahashi T. Chem. Asian J. 2006; 1: 370
    • 6c Yuan YQ, Fuse S, Ostash B, Sliz P, Kahne D, Walker S. ACS Chem. Biol. 2008; 3: 429
    • 6d Tanaka Y, Fuse S, Tanaka H, Doi T, Takahashi T. Org. Process Res. Dev. 2009; 13: 1111
    • 6e Ostash B, Doud EH, Lin C, Ostash I, Perlstein DL, Fuse S, Wolpert M, Kahne D, Walker S. Biochemistry 2009; 48: 8830
    • 6f Tanaka H, Tanaka Y, Minoshima M, Yamaguchi S, Fuse S, Doi T, Kawauchi S, Sugiyama H, Takahashi T. Chem. Commun. 2010; 46: 5942
    • 6g Takahashi J, Hijikuro I, Kihara T, Murugesh MG, Fuse S, Tsumura Y, Akaike A, Niidome T, Takahashi T, Sugimoto H. Bioorg. Med. Chem. Lett. 2010; 20: 1721
    • 6h Takahashi J, Hijikuro I, Kihara T, Murugesh MG, Fuse S, Kunimoto R, Tsumura Y, Akaike A, Niidome T, Okuno Y, Takahashi T, Sugimoto H. Bioorg. Med. Chem. Lett. 2010; 20: 1718
    • 6i Takagi M, Motohashi K, Nagai A, Izumikawa M, Tanaka M, Fuse S, Doi T, Iwase K, Kawaguchi A, Nagata K, Takahashi T, Shin-Ya K. Org. Lett. 2010; 12: 4664
    • 6j Machida K, Hirose Y, Fuse S, Sugawara T, Takahashi T. Chem. Pharm. Bull. 2010; 58: 87
    • 6k Serizawa T, Miyamoto S, Fuse S, Doi T, Takahashi T. Bull. Chem. Soc. Jpn. 2010; 83: 942
    • 6l Fuse S, Sugiyama S, Takahashi T. Chem. Asian J. 2010; 5: 2459
    • 6m Fuse S, Tsukamoto H, Yuan YQ, Wang TS. A, Zhang Y, Bolla M, Walker S, Sliz P, Kahne D. ACS Chem. Biol. 2010; 5: 701
    • 6n Ohshiro Y, Nakajima E, Goto Y, Fuse S, Takahashi T, Doi T, Suga H. ChemBioChem 2011; 12: 1183
    • 6o Fuse S, Okada K, Iijima Y, Munakata A, Machida K, Takahashi T, Takagi M, Shin-ya K, Doi T. Org. Biomol. Chem. 2011; 9: 3825
    • 6p Sugiyama S, Fuse S, Takahashi T. Tetrahedron 2011; 67: 6654
    • 6q Motohashi K, Inaba K, Fuse S, Doi T, Izumikawa M, Khan ST, Takagi M, Takahashi T, Shin-ya K. J. Nat. Prod. 2011; 74: 1630
    • 6r Fuse S, Machida K, Takahashi T. Efficient Synthesis of Natural Products Aided by Automated Synthesizers and Microreactors. In New Strategies in Chemical Synthesis and Catalysis. Pignataro B. Wiley-VCH; Weinheim: 2012: 33
    • 6s Fuse S, Inaba K, Takagi M, Tanaka M, Hirokawa T, Johmoto K, Uekusa H, Shin-Ya K, Takahashi T, Doi T. Eur. J. Med. Chem. 2013; 66: 180
    • 7a Fuse S, Masui H, Tannna A, Shimizu F, Takahashi T. ACS Comb. Sci. 2012; 14: 17
    • 7b Masui H, Fuse S, Takahashi T. Org. Lett. 2012; 14: 4090
    • 7c Fuse S, Tago H, Maitani MM, Wada Y, Takahashi T. ACS Comb. Sci. 2012; 14: 545
    • 8a Fuse S, Yoshida H, Takahashi T. Tetrahedron Lett. 2012; 53: 3288
    • 8b Fuse S, Sugiyama S, Maitani MM, Wada Y, Ogomi Y, Hayase S, Katoh R, Kaiho T, Takahashi T. Chem. Eur. J. 2014; DOI: 10.1002/chem.201402093.
    • 9a Fuse S, Tanabe N, Yoshida M, Yoshida H, Doi T, Takahashi T. Chem. Commun. 2010; 46: 8722
    • 9b Fuse S, Tanabe N, Takahashi T. Chem. Commun. 2011; 47: 12661
    • 9c Fuse S, Mifune Y, Tanabe N, Takahashi T. Org. Biomol. Chem. 2012; 10: 5205
    • 9d Fuse S, Tanabe N, Tannna A, Konishi Y, Takahashi T. Beilstein J. Org. Chem. 2013; 9: 2336
    • 9e Fuse S, Mifune Y, Takahashi T. Angew. Chem. Int. Ed. 2014; 53: 851
    • 9f Mifune Y, Fuse S, Tanaka H. J. Flow. Chem., in press
  • 10 Posner GH, Kahraman M. Eur. J. Org. Chem. 2003; 3889
    • 11a Doi T, Hijikuro I, Takahashi T. J. Am. Chem. Soc. 1999; 121: 6749
    • 11b Hijikuro I, Doi T, Takahashi T. J. Am. Chem. Soc. 2001; 123: 3716
    • 11c Doi T, Yoshida M, Hijikuro I, Takahashi T. Tetrahedron Lett. 2004; 45: 5727
  • 12 Zhu GD, Okamura WH. Chem. Rev. 1995; 95: 1877
    • 13a Kubodera N, Watanabe H. JP 188061, 1991
    • 13b Katoh M, Mikami T, Watanabe H. JP 72994, 1994
    • 13c Kubodera N, Watanabe H, Miyamoto K. JP 80626, 1994
    • 13d Rafael R, Andreas P. WO 128782, 2008
  • 14 Rappoldt MP, Havinga E. Recl. Trav. Chim. Pays-Bas 1960; 79: 369
    • 15a Han SY, Kim YA. Tetrahedron 2004; 60: 2447
    • 15b Montalbetti C, Falque V. Tetrahedron 2005; 61: 10827
    • 15c Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
    • 15d Pattabiraman VR, Bode JW. Nature (London, U.K.) 2011; 480: 471
    • 15e El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
  • 16 Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JJ. L, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green Chem. 2007; 9: 411
  • 17 Eckert H, Forster B. Angew. Chem., Int. Ed. Engl. 1987; 26: 894
    • 18a Suenaga K, Mutou T, Shibata T, Itoh T, Kigoshi H, Yamada K. Tetrahedron Lett. 1996; 37: 6771
    • 18b Mutou T, Suenaga K, Fujita T, Itoh T, Takada N, Hayamizu K, Kigoshi H, Yamada K. Synlett 1997; 199
    • 18c Takahashi T, Nagamiya H, Doi T, Griffiths PG, Bray AM. J. Comb. Chem. 2003; 5: 414
    • 18d Suenaga K, Mutou T, Shibata T, Itoh T, Fujita T, Takada N, Hayamizu K, Takagi M, Irifune T, Kigoshi H, Yamada K. Tetrahedron 2004; 60: 8509
    • 18e Suenaga K, Kajiwara S, Kuribayashi S, Handa T, Kigoshi H. Bioorg. Med. Chem. Lett. 2008; 18: 3902
    • 18f Sato S, Murata A, Orihara T, Shirakawa T, Suenaga K, Kigoshi H, Uesugi M. Chem. Biol. 2011; 18: 131