Polar tagging in the synthesis of monodisperse oligo(p-phenyleneethynylene) s and an update on the synthesis of oligoPPEs

Beilstein Journal of Organic Chemistry

Volumn 6, Issue , 2010, Pages

  Sahoo, Dhananjaya ^a   Thiele, Susanne ^a   Schulte, Miriam ^a   Ramezanian, Navid ^a   Godt, Adelheid ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Alkyne protecting group; C C coupling; Carbometalation; Phenyleneethynylene; Polar tagging

Indexed keywords

EID: 77955792403     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.6.57     Document Type: Article

References (82)

1. Daniell, H. W. ; Klotz, E. J. F. ; Odell, B. ; Claridge, T. D. W. ; Anderson, H. L. Angew. Chem. 2007, 119, 6969-6972. doi:10.1002/ange. 200702349
2. Tour, J. M. J. Org. Chem. 2007, 72, 7477-7496. doi:10.1021/jo070543s (Pubitemid 47501618)
3. Hu, W. ; Zhu, N. ; Tang, W. ; Zhao, D. Org. Lett. 2008, 10, 2669-2672. doi:10.1021/ol800753z
4. Blakskjær, P. ; Gothelf, K. V. Org. Biomol. Chem. 2006, 4, 3442-3447. doi:10.1039/b605844b (Pubitemid 44334856)
5. Andersen, C. S. ; Gothelf, K. V. Org. Biomol. Chem. 2009, 7, 58-60. doi:10.1039/b815099k
6. Ljungdahl, T. ; Pettersson, K. ; Albinsson, B. ; Mårtensson, J. Eur. J. Org. Chem. 2006, 3087-3096. doi:10.1002/ejoc. 200600240
7. Zhao, Y. ; Shirai, Y. ; Slepkov, A. D. ; Cheng, L. ; Alemany, L. B. ; Sasaki, T. ; Hegmann, F. A. ; Tour, J. M. Chem.-Eur. J. 2005, 11, 3643-3658. doi:10.1002/chem. 200401198
8. Huber, R. ; Gonzáles, M. T. ; Wu, S. ; Langer, M. ; Grunder, S. ; Horhoiu, V. ; Mayor, M. ; Bryce, M. R. ; Wang, C. ; Jitchati, R. ; Schönenberger, C. ; Calame, M. J. Am. Chem. Soc. 2008, 130, 1080-1084. doi:10.1021/ja0767940
9. Mayr, A. ; Srisailas, M. ; Zhao, Q. ; Gao, Y. ; Hsieh, H. ; Hoshmand-Kochi, M. ; St. Fleur, N. Tetrahedron 2007, 63, 8206-8217. doi:10.1016/j. tet. 2007. 05. 116
10. Guo, X. ; Whalley, A. ; Klare, J. E. ; Huang, L. ; O'Brien, S. ; Steigerwald, M. ; Nuckolls, C. Nano Lett. 2007, 7, 1119-1122. doi:10.1021/nl070245a (Pubitemid 46834383)
11. Lu, Q. ; Liu, K. ; Zhang, H. ; Du, Z. ; Wang, X. ; Wang, F. ACS Nano 2009, 3, 3861-3868. doi:10.1021/nn9012687
12. Jeschke, G. ; Sajid, M. ; Schulte, M. ; Godt, A. Phys. Chem. Chem. Phys. 2009, 11, 6580-6591. doi:10.1039/b905724b
13. Polyhach, Y. ; Godt, A. ; Bauer, C. ; Jeschke, G. J. Magn. Reson. 2007, 185, 118-129. doi:10.1016/j. jmr. 2006. 11. 012
14. Godt, A. ; Schulte, M. ; Zimmermann, H. ; Jeschke, G. Angew. Chem. 2006, 118, 7722-7726. doi:10.1002/ange. 200602807
15. Babgi, B. ; Rigamonti, L. ; Cifuentes, M. P. ; Corkery, T. C. ; Randles, M. D. ; Schwich, T. ; Petrie, S. ; Stranger, R. ; Teshome, A. ; Asselberghs, I. ; Clays, K. ; Samoc, M. ; Humphrey, M. G. J. Am. Chem. Soc. 2009, 131, 10293-10307. doi:10.1021/ja902793z
16. Ochi, T. ; Yamaguchi, Y. ; Wakamiya, T. ; Matsubara, Y. ; Yoshida, Z. Org. Biomol. Chem. 2008, 6, 1222-1231. doi:10.1039/b717832h (Pubitemid 351432843)
17. Albinsson, B. ; Mårtensson, J. J. Photochem. Photobiol. , C: Photochem. Rev. 2008, 9, 138-155. doi:10.1016/j. jphotochemrev. 2008. 01. 002
18. Myahkostupov, M. ; Piotrowiak, P. ; Wang, D. ; Galoppini, E. J. Phys. Chem. C 2007, 111, 2827-2829. doi:10.1021/jp0679257 (Pubitemid 46384288)
19. Yatabe, T. ; Suzuki, Y. ; Kawanishi, Y. J. Mater. Chem. 2008, 18, 4468-4477. doi:10.1039/b808036d
20. Lavastre, O. ; Ollivier, L. ; Dixneuf, P. H. ; Sibandhit, S. Tetrahedron 1996, 52, 5495-5504. doi:10.1016/0040-4020(96)00240-2 (Pubitemid 26109679)
21. Aujard, I. ; Baltaze, J.-P. ; Baudin, J.-B. ; Cogné, E. ; Ferrage, F. ; Jullien, L. ; Perez, E. ; Prévost, V. ; Qian, L. M. ; Ruel, O. J. Am. Chem. Soc. 2001, 123, 8177-8188. doi:10.1021/ja010019h (Pubitemid 32916393)
22. Hwang, J.-J. ; Tour, J. M. Tetrahedron 2002, 58, 10387-10405. doi:10.1016/S0040-4020(02)01409-6 (Pubitemid 35449365)
23. Zhi, Y.-G. ; Lai, S.-W. ; Chan, Q. K.-W. ; Law, Y.-C. ; Tong, G. S.-M. ; Che, C.-M. Eur. J. Org. Chem. 2006, 3125-3139. doi:10.1002/ejoc. 200600103
24. Nierengarten, J.-F. ; Gu, T. ; Hadziioannou, G. ; Tsamouras, D. ; Krasnikov, V. Helv. Chim. Acta 2004, 87, 2948-2966. doi:10.1002/hlca. 200490266 Another stepwise approach consisting of coupling with 4-iodobenzaldehyde and conversion of the aldehyde group into an ethyne moiety via the Corey-Fuchs reaction.
25. Huang, S. ; Tour, J. M. Tetrahedron Lett. 1999, 40, 3347-3350. doi:10.1016/S0040-4039(99)00463-3 (Pubitemid 29189384)
26. Zhang, J. ; Pesak, D. J. ; Ludwick, J. L. ; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227-4239. doi:10.1021/ja00089a012
27. Jones, L. , II; Schumm, J. S. ; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410.doi:10.1021/jo962336q
28. Li, G. ; Wang, X. ; Wang, F. Tetrahedron Lett. 2005, 46, 8971-8973. doi:10.1016/j. tetlet. 2005. 10.113
29. Hortholary, C. ; Coudret, C. J. Org. Chem. 2003, 68, 2167-2174. doi:10.1021/jo026735z (Pubitemid 36505090)
30. The use of the triflate group for the alkynyl-aryl coupling and its masking as the precursory OH group offers an alternative that was applied to the synthesis of phenyleneethynylene dendrimers [31], however, not (yet) to the synthesis of oligoPPEs.
31. Pan, Y. ; Peng, Z. ; Melinger, J. S. Tetrahedron 2003, 59, 5495-5506. doi:10.1016/S0040-4020(03)00827-5 (Pubitemid 36792220)
32. Kukula, H. ; Veit, S. ; Godt, A. Eur. J. Org. Chem. 1999, 277-286. doi:10.1002(SICI)1099-0690(199901)1999:1≤277::AID-EJOC277≥:13.0.CO;2-R
33. Wang, C. ; Batsanov, A. S. ; Bryce, M. R. J. Org. Chem. 2006, 71, 108-116. doi:10.1021/jo051711o (Pubitemid 43128066)
34. Chandra, K. L. ; Zhang, S. ; Gorman, C. B. Tetrahedron 2007, 63, 7120-7132. doi:10.1016/j. tet. 2007. 05. 006
35. We like to call attention to the recent reports that trimethylsilyl and HOP are orthogonal alkyne protecting groups which make HOP a very interesting protecting group [36,37]. The same is true for tert-butyldimethylsilyl and HOP [38].
36. Goeb, S. ; De Nicola, A. ; Ziessel, R. J. Org. Chem. 2005, 70, 1518-1529. doi:10.1021/jo048435i (Pubitemid 40300110)
37. Rodríguez, J. G. ; Esquivias, J. ; Lafuente, A. ; Díaz, C. J. Org. Chem. 2003, 68, 8120-8128. doi:10.1021/jo034972b (Pubitemid 37266572)
38. Shimizu, H. ; Fujimoto, K. ; Furusyo, M. ; Maeda, H. ; Nanai, Y. ; Mizuno, K. ; Inouye, M. J. Org. Chem. 2007, 72, 1530-1533. doi:10.1021/jo061959t
39. Ziener, U. ; Godt, A. J. Org. Chem. 1997, 62, 6137-6143. doi:10.1021/jo970548x
40. Acharya, J. R. ; Zhang, H. ; Li, X. ; Nesterov, E. E. J. Am. Chem. Soc. 2009, 131, 880-881. doi:10.1021/ja807621z
41. Hsung, R. P. ; Chidsey, C. E. D. ; Sita, L. R. Organometallics 1995, 14, 4808-4815. doi:10.1021/om00010a049
42. Ley, K. D. ; Li, Y. ; Johnson, J. V. ; Powell, D. H. ; Schanze, K. S. Chem. Commun. 1999, 1749-1750. doi:10.1039/a903476e
43. Li, G. ; Wang, X. ; Li, J. ; Zhao, X. ; Wang, F. Tetrahedron 2006, 62, 2576-2582. doi:10.1016/j. tet. 2005. 12. 043
44. Pearson, D. L. ; Tour, J. M. J. Org. Chem. 1997, 62, 1376-1387. doi:10.1021/jo962335y
45. Zeng, X. ; Wang, C. ; Bryce, M. R. ; Batsanov, A. S. ; Sirichantaropass, S. ; García-Suárez, V. M. ; Lambert, C. J. ; Sage, I. Eur. J. Org. Chem. 2007, 5244-5249. doi:10.1002/ejoc. 200700507
46. Maag, D. ; Kottke, T. ; Schulte, M. ; Godt, A. J. Org. Chem. 2009, 74, 7733-7742. doi:10.1021/jo9009744
47. Yang, J. ; Ng, M.-K. Synthesis 2006, 3075-3079. doi:10.1055/s-2006-942529 (Pubitemid 44525957)
48. Robinson, J. M. A. ; Kariuki, B. M. ; Harris, K. D. M. ; Philp, D. J. Chem. Soc. , Perkin Trans. 2 1998, 2459-2469. doi:10.1039/a804676j
49. Harriman, A. ; Mallon, L. ; Ziessel, R. Chem.-Eur. J. 2008, 14, 11461-11473. doi:10.1002/chem. 200801384
50. Zhao, Z. ; Yu, S. ; Xu, L. ; Wang, H. ; Lu, P. Tetrahedron 2007, 63, 7809-7815. doi:10.1016/j. tet. 2007. 05. 095
51. Rodríguez, J. G. ; Tejedor, J. L. J. Org. Chem. 2002, 67, 7631-7640. doi:10.1021/jo0203589 (Pubitemid 35239655)
52. Kaneko, T. ; Horie, T. ; Matsumoto, S. ; Teraguchi, M. ; Aoki, T. Macromol. Chem. Phys. 2009, 210, 22-36. doi:10.1002/macp. 200800429
53. Takayama, Y. ; Delas, C. ; Muraoka, K. ; Uemura, M. ; Sato, F. J. Am. Chem. Soc. 2003, 125, 14163-14167. doi:10.1021/ja037975e (Pubitemid 37424015)
54. López, S. ; Fernández-Trillo, F. ; Midón, P. ; Castedo, L. ; Saá, C. J. Org. Chem. 2006, 71, 2802-2810.doi:10.1021/ jo052609u
55. Silicon based alkyne protecting groups with a cyano group as the polar tag [54,56,57].
56. Höger, S. ; Bonrad, K. J. Org. Chem. 2000, 65, 2243-2245. doi:10.1021/jo991746m (Pubitemid 30193918)
57. Gaefke, G. ; Höger, S. Synthesis 2008, 2155-2157. doi:10.1055/s-2008-1067141
58. Keller, J. M. ; Schanze, K. S. Organometallics 2009, 28, 4210-4216. doi:10.1021/om900195p
59. Weibel, N. ; Mishchenko, A. ; Wandlowski, T. ; Neuburger, M. ; Leroux, Y. ; Mayor, M. Eur. J. Org. Chem. 2009, 6140-6150. doi:10.1002/ejoc. 200900751
60. Bumagin, N. A. ; Ponomaryov, A. B. ; Beletskaya, I. P. Synthesis 1984, 728-729. doi:10.1055/s-1984-30947
61. Atkinson, R. E. ; Curtis, R. F. ; Jones, D. M. ; Taylor, J. A. J. Chem. Soc. C 1969, 2173-2176. doi:10.1039/J39690002173 The suggestion to use the HOM group as a protecting group that can be removed via oxidation-decarbonylation was made much earlier here.
62. The largely different reaction times given in the experimental part of [48] probably indicate that the experimenters of that reference experienced the same difficulties.
63. Burke, S. D. ; Danheiser, R. L. , Eds. Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents; Wiley: Chichester, U. K. , 2004; p 232.
64. Fatiadi, A. J. Synthesis 1976, 65-104. doi:10.1055/s-1976-23961
65. 4 (160 g) and of solvent was used in comparison to the procedure given in [64].
66. As purchased; 80% technical grade.
67. Fatiadi, A. J. Synthesis 1987, 85-127. doi:10.1055/s-1987-27859
68. Firouzabadi, H. ; Ghaderi, E. Tetrahedron Lett. 1978, 19, 839-840. doi:10.1016/S0040-4039(01)85412-5
69. 2 has been reported [70]. The alkene isomerization can also be explained by a reversible addition of hydroxide to the electron acceptor substituted alkene of aldehyde 6a. Characteristic signals of the major isomer: d = 9. 38 (d, J = 8. 2 Hz, 1 H, CHO), 7. 32 and 7. 00 (2 s, 1 H each, ArH), 6. 47 (d, J = 8. 2 Hz, 1 H, C=CH); Characteristic signals of the minor isomer: d = 10.28 (d, J = 8. 2 Hz, 1 H, CHO), 7. 30 and 7. 09 (2 s, 1 H each, ArH), 6. 31 (d, J = 8. 2 Hz, 1 H, C=CH).
70. Burrell, J. W. K. ; Garwood, R. F. ; Jackman, L. M. ; Oskay, E. ; Weedon, B. C. L. J. Chem. Soc. C 1966, 2144-2154. doi:10.1039/J39660002144
71. 2OH).
72. We know of only two publications that report on carbometalation of 1-aryl-2-trialkylsilylethynes [73,74]. The carbometalation reported in is possibly induced by the hydroxy group of the hydroxymethyl substituent in ortho-position to the 2-(trimethylsilyl)ethynyl group. Note also the related Pd-catalyzed addition of TMSethyne onto 3-(trimethylsilyl)prop-2-ynol giving Z-2-(2-trimethylsilylethynyl)-3-trimethylsilylprop-2-enol in [75]
73. Stará, I. G. ; Starý, I. ; Kollárovic, A. ; Teplý, F. ; Šaman, D. ; Fiedler, P. Tetrahedron 1998, 54, 11209-11234. doi:10.1016/S0040-4020(98)00655-3
74. Batenburg-Nguyen, B. ; Ung, A. T. ; Pyne, S. G. Tetrahedron 2009, 65, 318-327. doi:10.1016/j. tet. 2008. 10.052
75. Trost, B. M. ; McIntosh, M. C. Tetrahedron Lett. 1997, 38, 3207-3210.doi:10.1016/S0040-4039(97)00614-X (Pubitemid 27193168)
76. Mal'kina, A. G. ; Brandsma, L. ; Vasilevsky, S. F. ; Trofimov, B. A. Synthesis 1996, 589-590. doi:10.1055/s-1996-4265
77. McQuade, D. T. ; Kim, J. ; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885-5886. doi:10.1021/ja000553+ (Pubitemid 30432296)
78. Werz, D. B. ; Fischer, F. R. ; Kornmayer, S. C. ; Rominger, F. ; Gleiter, R. J. Org. Chem. 2008, 73, 8021-8029. doi:10.1021/jo801378p
79. 1H NMR spectrum of the crude product reveal.
80. Bao, Z. ; Chen, Y. ; Cai, R. ; Yu, L. Macromolecules 1993, 26, 5281-5286. doi:10.1021/ma00072a002
81. The eight step synthesis is outlined in analogy to the synthesis of the corresponding oligoPPE diesters in [82]. The eight step route is to be preferred over the seven step route because of the instability of oligoPPEs with two unprotected terminal ethyne moieties.
82. Hensel, V. ; Godt, A. ; Popovitz-Biro, R. ; Cohen, H. ; Jensen, T. R. ; Kjaer, K. ; Weissbuch, I. ; Lifshitz, E. ; Lahav, M. Chem.-Eur. J. 2002, 8, 1413-1423. doi:10.1002/1521-3765(20020315)8:63.0.CO;2-6 (Pubitemid 34259562)