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RESEARCH ARTICLE
Contents Vol 68(11)

A Facile Preparation of α-Aryl Carboxylic Acid via One-Flow Arndt–Eistert Synthesis

Shinichiro Fuse A B C , Yuma Otake A , Yuto Mifune A and Hiroshi Tanaka A
+ Author Affiliations
- Author Affiliations

A Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo 152-8552, Japan.

B Current address: Chemical Resources Laboratory, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.

C Corresponding author. Email: sfuse@res.titech.ac.jp

Australian Journal of Chemistry 68(11) 1657-1661 https://doi.org/10.1071/CH15342
Submitted: 10 June 2015  Accepted: 14 July 2015   Published: 11 August 2015

Abstract

An efficient, one-flow Arndt–Eistert synthesis was demonstrated. A sequence of acid chloride formation–nucleophilic acyl substitution–Wolff rearrangement–nucleophilic addition was performed in a microflow system without isolating any intermediates, which included a potentially explosive compound. The microflow system was made from simple, inexpensive, and readily available instruments and tubes. α-Aryl esters 2a and 2b were prepared in yields of 33 and 23 % (three steps) respectively.


References

[1]  (a) F. Arndt, B. Eistert, W. Partale, Ber. Dtsch. Chem. Ges. 1927, 60, 1364.
         | Crossref | GoogleScholarGoogle Scholar |
         (b) W. E. Bachmann, W. S. Struve, in Organic Reactions (Ed. R. Adams) 1942, Vol. 1, Ch. 2, pp. 38–54 (John Wiley & Sons, Inc.: New York, NY).

[2]  B. J. Deadman, S. G. Collins, A. R. Maguire, Chem. – Eur. J. 2015, 21, 2298.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhvFGisLbJ&md5=95614b074b29aeadbd1e4ecdf0d9b070CAS | 25404044PubMed |

[3]  (a) L. Wolff, Justus Liebigs Ann. Chem. 1902, 325, 129.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) W. Kirmse, Eur. J. Org. Chem. 2002, 2193.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) M. S. Newman, P. F. Beal, J. Am. Chem. Soc. 1950, 72, 5163.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3MXjs1Sqsw%3D%3D&md5=4ab2e386b7723f490cb6c8f988c778a9CAS |
      (b) J.-Y. Winum, M. Kamal, A. Leydet, J.-P. Roque, J.-L. Montero, Tetrahedron Lett. 1996, 37, 1781.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) J.-i. Yoshida, Chem. Rec. 2010, 10, 332.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXht1yktLbJ&md5=bbb9b5aec37ec62df03d2bdefe896c58CAS |
         (b) S. V. Luis, E. Carcia-Verdugo, Chemical Reactions and Processes Under Flow Conditions 2010 (Royal Society of Chemistry: Cambridge, UK).
      (c) J. P. McMullen, K. F. Jensen, Annu. Rev. Anal. Chem. 2010, 3, 19.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J.-i. Yoshida, H. Kim, A. Nagaki, ChemSusChem 2011, 4, 331.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Baumann, I. R. Baxendale, S. V. Ley, Mol. Divers. 2011, 15, 613.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. Wegner, S. Ceylan, A. Kirschning, Chem. Commun. 2011, 4583.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J. Wegner, S. Ceylan, A. Kirschning, Adv. Synth. Catal. 2012, 354, 17.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) J. P. Knowles, L. D. Elliott, K. I. Booker-Milburn, Beilstein J. Org. Chem. 2012, 8, 2025.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) I. R. Baxendale, C. Hornung, S. V. Ley, J. M. Muñoz Molina, A. Wikström, Aust. J. Chem. 2013, 66, 131.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) N. G. Anderson, Org. Process Res. Dev. 2012, 16, 852.
         | Crossref | GoogleScholarGoogle Scholar |
         (k) T. Wirth, Microreactors in Organic Chemistry and Catalysis 2013 (Wiley-VCH: Weinheim).
      (l) L. N. Protasova, M. Bulut, D. Ormerod, A. Buekenhoudt, J. Berton, C. V. Stevens, Org. Process Res. Dev. 2013, 17, 760.
         | Crossref | GoogleScholarGoogle Scholar |
      (m) J. C. Pastre, D. L. Browne, S. V. Ley, Chem. Soc. Rev. 2013, 42, 8849.
         | Crossref | GoogleScholarGoogle Scholar |
      (n) V. Hessel, D. Kralisch, N. Kockmann, T. Noël, Q. Wang, ChemSusChem 2013, 6, 746.
         | Crossref | GoogleScholarGoogle Scholar |
      (o) H. Amii, A. Nagaki, J.-i. Yoshida, Beilstein J. Org. Chem. 2013, 9, 2793.
         | Crossref | GoogleScholarGoogle Scholar |
      (p) R. M. Myers, D. E. Fitzpatrick, R. M. Turner, S. V. Ley, Chem. – Eur. J. 2014, 20, 12348.
         | Crossref | GoogleScholarGoogle Scholar |
      (q) S. Ramesh, P. Cherkupally, B. de la Torre, T. Govender, H. Kruger, F. Albericio, Amino Acids 2014, 46, 2091.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) Y. Matsushita, T. Ichimura, N. Ohba, S. Kumada, K. Sakeda, T. Suzuki, H. Tanibata, T. Murata, Pure Appl. Chem. 2007, 79, 1959.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtlartbfO&md5=a6c4c7bbc6dc963d9421d522d2f62ccdCAS |
      (b) E. E. Coyle, M. Oelgemoller, Photochem. Photobiol. Sci. 2008, 7, 1313.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Oelgemöller, O. Shvydkiv, Molecules 2011, 16, 7522.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) M. Oelgemöller, Chem. Eng. Technol. 2012, 35, 1144.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) Y. Su, N. J. W. Straathof, V. Hessel, T. Noël, Chem. – Eur. J. 2014, 20, 10562.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) E. M. Schuster, P. Wipf, Isr. J. Chem. 2014, 54, 361.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) Rapid optimization of photoreactions using parallel microflow reactors has been reported; see: A. Yavorskyy, O. Shvydkiv, N. Hoffmann, K. Nolan, M. Oelgemöller, Org. Lett. 2012, 14, 4342.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) N. M. Reis, G. Li Puma, Chem. Commun. 2015, 8414.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  Y. S. M. Vaske, M. E. Mahoney, J. P. Konopelski, D. L. Rogow, W. J. McDonald, J. Am. Chem. Soc. 2010, 132, 11379.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptFOksr8%3D&md5=89d6e8686a867a12a3ebfaf70d647beaCAS |

[8]  T. P. Willumstad, O. Haze, X. Y. Mak, T. Y. Lam, Y.-P. Wang, R. L. Danheiser, J. Org. Chem. 2013, 78, 11450.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1Sqs7rO&md5=35c3581987bbcc2065f1ae598362c67aCAS | 24116731PubMed |

[9]  S. Garbarino, L. Banfi, R. Riva, A. Basso, J. Org. Chem. 2014, 79, 3615.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXkvVCrtrc%3D&md5=ce9883c8d8a478a6c804ef2ae5b6eed4CAS | 24665997PubMed |

[10]  F. Mastronardi, B. Gutmann, C. O. Kappe, Org. Lett. 2013, 15, 5590.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1ejtL7I&md5=791afd3b4072c7ee102e0a927b2c93e7CAS | 24128181PubMed |

[11]  V. D. Pinho, B. Gutmann, C. O. Kappe, RSC Adv. 2014, 4, 37419.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtlCkt7zF&md5=e24a6290b09d9e39d9a2a4eb2fbb4295CAS |

[12]  (a) S. Fuse, N. Tanabe, M. Yoshida, H. Yoshida, T. Doi, T. Takahashi, Chem. Commun. 2010, 8722.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVahurbK&md5=0099b10527d0d817b28e7e4a54e97266CAS |
      (b) S. Fuse, N. Tanabe, T. Takahashi, Chem. Commun. 2011, 12661.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Fuse, Y. Mifune, N. Tanabe, T. Takahashi, Org. Biomol. Chem. 2012, 10, 5205.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) S. Fuse, N. Tanabe, A. Tannna, Y. Konishi, T. Takahashi, Beilstein J. Org. Chem. 2013, 9, 2336.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) S. Fuse, Y. Mifune, T. Takahashi, Angew. Chem. Int. Ed. 2014, 53, 851.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) Y. Mifune, S. Fuse, H. Tanaka, J. Flow Chem. 2014, 4, 173.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  J. D. O’Neil, M. K. Bamat, B. R. W. Von, S. Sharma, R. Arudchandran, U.S. Patent 2009 037128 2009.

[14]  Z. Du, W. Li, X. Zhu, F. Xu, Q. Shen, J. Org. Chem. 2008, 73, 8966.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlGns7bJ&md5=6561cbf07cadc3bf25893eb7059bdbb4CAS | 18937411PubMed |

[15]  Acid chloride formation using exactly the same substrate has been reported (SOCl2, 1,4-dioxane, reflux, overnight, 99 %); see: S. Belyakov, G. Hamilton, D. Limburg, J. Steiner, M. Vaal, L. Wei, D. Wilkinson, Y. Q. Wu, U.S. Patent 2002 002538 2002.

[16]  T. Aoyama, T. Shioiri, Tetrahedron Lett. 1980, 21, 4461.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3MXhtl2nsrs%3D&md5=f591f8f3fccf43b98f807cebf261b4efCAS |

[17]  A. Padwa, R. Layton, Tetrahedron Lett. 1965, 6, 2167.
         | Crossref | GoogleScholarGoogle Scholar |