Site-selectively functionalizing microelectrode arrays: The use of Cu(I)-catalysts

Langmuir

Volumn 27, Issue 17, 2011, Pages 11199-11205

  Bartels, Jennifer ^a   Lu, Peng ^b   Maurer, Karl ^c   Walker, Amy V ^b   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b The University of Texas at Dallas   (United States)

^c CombiMatrix Corporation ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL IODIDES; CATALYZED REACTIONS; CLICK REACTION; DIVIDED CELL; MICROELECTRODE ARRAY; PRE-SELECTED; REACTION LAYERS; SITE SELECTIVE; UNDIVIDED CELL;

CATALYSIS; CATALYSTS; ELECTROLYSIS; SUGARS; SULFUR;

MICROELECTRODES;

EID: 80052215729     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la201881k     Document Type: Article

References (50)

1. Patai Series: The Chemistry of Organocopper Compounds, Rappaport, Z. Z.; Marek, I., Eds; Wiley: New York, 2010.
2. For a description of the chips used here, see Dill, K.; Montgomery, D. D.; Wang, W.; Tsai, J. C. Anal. Chim. Acta 2001, 444, 69 1K chips: electrode diameter = 92 μm; Distance between the Pt-electrodes (rectangular cells) = 245.3 and 337.3 μm; 12K slide: diameter = 44 μm; Distance between the Pt-electrodes (square cells) = 33 μm.
3. Sullivan, M. G.; Utomo, H.; Fagan, P. J.; Ward, M. D. Anal. Chem. 1999, 71, 4369
4. Zhang, S.; Zhao, H.; John, R. Anal. Chim. Acta 2000, 421, 175
5. Hintsche, R.; Albers, J.; Bernt, H.; Eder, A. Electroanalysis 2000, 12, 660
6. Gardner, R. D.; Zhou, A.; Zufelt, N. A. Sens. Actuators, B 2009, 136, 177
7. Beyer, M.; Nesterov, A.; Block, I.; König, K.; Felgenhauer, T.; Fernandez, S.; Leibe, K.; Torralba, G.; Hausmann, M.; Trunk, U.; Lindenstruth, V.; Bischoff, F. R.; Stadler, V.; Breitling, F. Science 2007, 318, 1888
8. Devaraj, N. K.; Dinolfo, P. H.; Chidsey, C. E. D.; Collman, J. P. J. Am. Chem. Soc. 2006, 128, 1794
9. Wassum, K. M.; Tolosa, V. M.; Wang, J.; Walker, E.; Monbouquette, H. G.; Maidment, N. T. Sensors 2008, 8, 5023
10. Kerkoff, H. G.; Zhang, X.; Mailly, F.; Nouet, P.; Liu, H.; Richardson, A. VLSI Design 2008, Article ID 437879 (doi: 10.1155/2008/437879).
11. Zhang, Y.; Wnag, H.; Nie, J.; Zhang, Y.; Shen, G.; Yu, R. Biosens. Bioelectron. 2009, 25, 34
12. Maurer, K.; Yazvenko, N.; Wilmoth, J.; Cooper, J.; Lyon, W.; Danley, D. Sensors 2010, 10, 7371
13. Li, X.; Tian, Y.; Xia, P.; Luo, Y.; Rui, Q. Anal. Chem. 2009, 81, 8249
14. Chan, E. W. L.; Yousaf, M. N. ChemPhysChem 2007, 8, 1469
15. Tesfu, E.; Roth, K.; Maurer, K.; Moeller, K. D. Org. Lett. 2006, 8, 709
16. Stuart, M.; Maurer, K.; Moeller, K. D. Bioconjugate Chem. 2008, 19, 1514
17. For an example, see: Hu, L.; Bartels, J. L.; Bartels, J. W.; Maurer, K.; Moeller, K. D. J. Am. Chem. Soc. 2009, 131, 16638
18. Tesfu, E.; Roth, K.; Maurer, K.; Moeller, K. D. Org. Lett. 2006, 8, 709
19. Tesfu, E.; Maurer, K.; Ragsdale, S. R.; Moeller, K. D. J. Am. Chem. Soc. 2004, 126, 6212
20. Tesfu, E.; Maurer, K.; McShae, A.; Moeller, K. D. J. Am. Chem. Soc. 2006, 128, 70
21. Tian, J.; Maurer, K.; Tesfu, E.; Moeller, K. D. J. Am. Chem. Soc. 2005, 127, 1392
22. Tian, J.; Maurer, K.; Moeller, K. D. Tetrahedron Lett. 2008, 49, 5664
23. Hu, L.; Maurer, K.; Moeller, K. S. Org. Lett. 2009, 11, 1273
24. Hu, L.; Stuart, M.; Tian, J.; Maurer, K.; Moeller, K. D. J. Am. Chem. Soc. 2010, 132, 16610
25. For examples of the site-selective generation of base, see ref 5b and Maurer, K.; McShea, A.; Strathmann, M.; Dill, K. J. Comb. Chem. 2005, 7, 637
26. For the site-selective generation of acid: Kesselring, D.; Maurer, K.; Moeller, K. D. Org. Lett. 2008, 10, 2501
27. For the use of CAN in a site-selective fashion: Kesselring, D.; Maurer, K.; Moeller, K. D. J. Am. Chem. Soc. 2008, 130, 11290
28. For the site-selective use of Sc(III), see Bi, B.; Maurer, K.; Moeller, K. D. Angew. Chem., Int. Ed. Engl. 2009, 48, 5872
29. Bartels, J. L.; Lu, P.; Walker, A.; Maurer, K.; Moeller, K. D. Chem. Commun. 2009, 5573
30. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
31. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428
32. Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581
33. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793
34. Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205. For reactions with alcohol nucleophiles, see
35. Wolter, M.; Nordmann, G.; Job, G. F.; Buchwald, S. L. Org. Lett. 2002, 4, 973
36. A., R.; Shafir, A.; Choi, A.; Lichtor, P. A.; Buchwald, S. L. J. Org. Chem. 2008, 73, 284
37. Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem.-Eur. J. 2006, 12, 3636
38. (mini review) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954.
39. Rivero, M. R.; Buchwald, S. L. Org. Lett. 2007, 9, 973
40. Martin, R.; Rivero, M. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079
41. Kabir, M. S.; Van Linn, M. L.; Monte, A.; Cook, J. M. Org. Lett. 2008, 10, 3363
42. Bates, C. G.; Saejueng, P. S.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005
43. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490
44. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863
45. For the synthesis of the benzotriazepine, see Yotphan, S.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2009, 11, 1511
46. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174 (mini review).
47. Do, H. Q.; Khan, R. M.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185
48. Do, H. Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 1240
49. Yoshizumi, T.; Tsurugi, H.; Satoh, T.; Miura, M. Tetrahedron Lett. 2008, 49, 1598
50. Chen, C.; Walker, A.; Maurer, K.; Moeller, K. D. Electrochem. Commun. 2008, 10, 973