Rapid and highly selective copper-free sonogashira coupling in high-pressure, high-temperature water in a microfluidic system

Angewandte Chemie - International Edition

Volumn 46, Issue 27, 2007, Pages 5129-5132

  Kawanami, Hajime ^a   Matsushima, Keiichiro ^a,b   Sato, Masahiro ^a   Ikushima, Yutaka ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b HOKKAIDO INDUSTRIAL RESEARCH INSTITUTE   (Japan)

Author keywords

C C coupling; High pressure chemistry; High temperature chemistry; Microreactors; Water chemistry

Indexed keywords

HIGH PRESSURE CHEMISTRY; HIGH TEMPERATURE CHEMISTRY; MICROREACTORS; WATER CHEMISTRY;

COPPER; HEATING; HIGH PRESSURE EFFECTS; HIGH TEMPERATURE EFFECTS; LIGANDS; ORGANIC SOLVENTS; REACTION KINETICS; WATER;

MICROFLUIDICS;

ACETYLENE; COPPER; DRUG DERIVATIVE; IODIDE; PHENYLACETYLENE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; INSTRUMENTATION; METHODOLOGY; MICROFLUIDICS; PRESSURE; TEMPERATURE; TIME;

ACETYLENE; COPPER; IODIDES; MICROFLUIDICS; MOLECULAR STRUCTURE; PRESSURE; SPECTROPHOTOMETRY, INFRARED; TEMPERATURE; TIME FACTORS; WATER;

EID: 34447299715     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700611     Document Type: Article

References (60)

1. For examples of C-C coupling reactions with transition-metal catalysts, see the following articles and books, and references cited therein: a) K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49:
2. b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
3. c) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985;
4. d) K. Sonogashira in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
5. e) J. A. Marsden, M. M. Haley in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
6. a) I. Paterson, R. D. Davies, R. Marquez, Angew. Chem. 2001, 113, 623-627;
7. Angew. Chem. Int. Ed. 2001, 40, 603-607;
8. b) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1461;
9. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416;
10. c) U. H. F. Bunz, Chem. Rev. 2000, 100, 1605-1644.
11. For reviews that feature the Sonogashira coupling, see: a) R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 872-922;
12. b) H. Doucet, J.-C. Hierso, Angew. Chem. 2007, 119, 850-888;
13. Angew. Chem. Int. Ed. 2007, 46, 834-871;
14. c) R. R. Tykwinski, Angew. Chem. 2003, 115, 1604-1606;
15. Angew. Chem. Int. Ed. 2003, 42, 1566-1568;
16. d) E. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-2017;
17. e) R. Rossi, A. Carpita, F. Bellina, Org. Prep. Proced. Int. 1995, 27, 127-160.
18. a) W. A. Herrmann, C.-P. Resinger, P. Harter in Aqueous-Phase Organometallic Catalysis, 2nd ed. (Eds: V. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2004, p.511-523;
19. b) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 1995.
20. For transition-metal-free C-C coupling in water with microwave irradiation, but with insufficient yields, see: P. Appukkuttan, W. Dehaen, E. van der Eycken, Eur. J. Org. Chem. 2003, 4713-4716.
21. For recent reviews and books, see: a) V. Hassel, S. Hardt, H. Lowe, Chemical Micro Process Engineering: Fundamentals, Modelling and Reactions, Wiley-VCH, Weinheim, 2004;
22. b) W. Ehrfeld, V. Hessel, H. Lowe, Microreactor: New Technology for Modern Chemistry, Wiley-VCH, Weinheim, 2000;
23. c) P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong, X. Zhang, Tetrahedron 2002, 58, 4735;
24. d) K. Jahnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 385;
25. Angew. Chem. Int. Ed. 2004, 43, 406:
26. e) P. Watts, S. J. Haswell, Chem. Soc. Rev. 2005, 34, 235;
27. f) A. J. deMello, Nature 2006, 442, 394-402.
28. For selected recent examples of the Sonogashira coupling in water, see: a) K. W. Anderson, S. L. Buchwald, Angew. Chem. 2005, 117, 6329-6333;
29. Angew. Chem. Int. Ed. 2005, 44, 6173-6177;
30. b) Y. Uozumi, Y. Kobayashi, Heterocycles 2003, 59, 71-74;
31. c) L. Chena, C.-J. Lib, Adv. Synth. Catal. 2006, 348, 1459-1484;
32. d) S. Raju, P. R. Kumar, K. Mukkanti, P. Annamalai, M. Pal, Bioorg. Med. Chem. Lett. 2006, 16, 6185-6189;
33. e) Z. Novák, A. Szabó, J. Répási, A. Kotschy, J. Org. Chem. 2003, 68, 3327-3329;
34. f) S. Bhattacharya, S. Sengupta, Tetrahedron Lett. 2004, 45, 8733-8736;
35. g) J. Gil-Moltó, C. Nájera, Eur. J. Org. Chem. 2005, 4073-4081;
36. h) C. Najera, J. Gil-Molto, S. Karistrom, L. R. Falvello, Org. Lett. 2003, 5, 1451-1454.
37. For selected reports on chemical reactions in microreactors under high-pressure conditions (including supercritical conditions), see: a) Y. Ikushima, K. Hatakeda, O. Sato, M. Sato, M. Arai, Chem. Commun. 2002, 2208-2209;
38. b) J. Kobayashi, Y. Mori, S. Kobayashi, Chem. Commun. 2005, 2567-2568;
39. c) E. Garcia-Verdugo, Z. Liu, E. Ramirez, J. Garcia-Serna, J. Fraga-Dubreuil, J. R. Hyde, P. A. Hamley, M. Poliakoff, Green Chem. 2006, 8, 359-364.
40. For selected reports on C-C coupling (Suzuki-Miyaura coupling) with microwave irradiation in microcapillaries, see: a) E. Comer, M. G. Organ, J. Am. Chem. Soc. 2005, 127, 8160-8167:
41. b) E. Comer, M. G. Organ, Chem. Eur. J. 2005, 11, 7223-7227:
42. c) N. T. S. Phan, J. Khan, P. Styring, Tetrahedron 2005, 61, 12 065-12 073.
43. For a recent example or copper-free Sonogashira coupling in a microflow system, see: T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, I. Ryu, Org. Lett. 2002, 4, 1961-1964.
44. a) W. L. Marshall, E. U. Franck, J. Phys. Chem. Ref. Data 1981, 10, 295-304;
45. b) Y. Ikushima, M. Arai in Chemical Synthesis Using Supercritical Fluids (Eds: P. G. Jessop, W. Leitner), Wiley-VCH, Weinheim, 1999, p.259-279.
46. a) M. Siskin, A. R. Katritzky, Science 1991, 254, 231-239;
47. b) D. Bröll, C. Kaul, A. Krämer, P. Krammer, T. Richter, M. Jung, H. Vogel, P. Zehner, Angew. Chem. 1999, 111, 3180-3196;
48. Angew. Chem. Int. Ed. 1999, 38, 2998-3014;
49. c) Y. Ikushima, K. Hatakeda, O. Sato, T. Yokoyama, M. Arai, J. Am. Chem. Soc. 2000, 122, 1908-1918.
50. 3, the product was formed in a lower yield of 29 and 64%, respectively, under the conditions for run 10 in Table 1.
51. High-pressure and high-temperature view cells were attached after the micromixers 7 and 11 in Figure 2.
52. a) S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. 2005, 117, 3339-3343;
53. Angew. Chem. Int. Ed. 2005, 44, 3275-3279;
54. b) J. E. Klijn, J. B. F. N. Engberts, Nature 2005, 435, 746-747.
55. s) under atmospheric pressure for 2a was obtained from the database SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (National Institute of Advanced Industrial Science and Technology, 22/02/2006).
56. a) P. Raveendran, Y. Ikushima, S. L. Wallen, Acc. Chem. Res. 2005, 38, 478-485;
57. b) K. P. Johnston, K. L. Harrison, M. J. Clarke, S. M. Howdle, M. P. Heitz, F. V. Bright, C. Carlier, T. W. Randolph, Science 1996, 271, 624.
58. A. J. Belsky, P. G. Maiella, T. B. Brill, J. Phys. Chem. A 1999, 103, 4253-4260.
59. H. Takahashi, S. Hisaoka, T. Nitta, Chem. Phys. Lett. 2002, 363, 80-86.
60. M. Boero, T. Ikeshoji, C. C. Liew, K. Terakurra, M. Parrinello, J. Am. Chem. Soc. 2004, 126, 6280-6286.