A modular approach to catalytic synthesis using a dual-functional linker for Click and Suzuki coupling reactions

Tetrahedron Letters

Volumn 51, Issue 30, 2010, Pages 3913-3917

  White, James R ^a   Price, Gareth J ^a   Schiffers, Stefanie ^a   Raithby, Paul R ^a   Plucinski, Pawel K ^b   Frost, Christopher G ^a  

^a University of Bath Claverton Down   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; BENZYLAZIDOBORONATE ESTER; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLICK COUPLING REACTION; CYCLOADDITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 77953687035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.104     Document Type: Article

References (50)

1. Cane D.E., Walsh C.T., and Khosla C. Science 282 (1998) 63-68
2. Sharpless K.B., Finn M.G., and Kolb H.C. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
3. Kolb H.C., and Sharpless K.B. Drug Discovery Today 8 (2003) 1128-1137
4. Boyle P.M., and Silver P.A. J. R. Soc. Interface 6 (2009) S535-S546
5. Trost B.M. Science 227 (1985) 908-916
6. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
7. Tornoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
8. Lutz J.-F. Angew. Chem., Int. Ed. 46 (2007) 1018-1025
9. Moses J.E., and Moorhouse A.D. Chem. Soc. Rev. 36 (2007) 1249-1262
10. Meldal M., and Tornøe C.W. Chem. Rev. 108 (2008) 2952-3015
11. Sumerlin B.S., and Vogt A.P. Macromolecules 43 (2010) 1-13
12. Matteson D.S. J. Organomet. Chem. 581 (1999) 51-65
13. In: Hall D.G. (Ed). Boronic Acids-Preparation, Applications in Organic Synthesis and Medicine (2005), Wiley-VCH, Weinheim
14. Kotha S., and Lahiri K. Eur. J. Org. Chem. (2007) 1221-1236
15. Stefani H.A., Cella R., and Vieira A.S. Tetrahedron 63 (2007) 3623-3658
16. Gillis E.P., and Burke M.D. J. Am. Chem. Soc. 130 (2008) 14084-14085
17. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685-4696
18. Bedford R.B., Nakamura M., Gower N.J., Haddow M.F., Hall M.A., Huwe M., Hashimoto T., and Okopie R.A. Tetrahedron Lett. 50 (2009) 6110-6111
19. Torborga C., and Beller M. Adv. Synth. Catal. 351 (2009) 3027-3043
20. For selected discussions on the incompatibility, stability and safety of azides, see Refs. 3a and 1b;. Conrow R.E., and Dean W.D. Org. Process Res. Dev. 12 (2008) 1285-1286
21. Fedorov A.Yu., Shchepalov A.A., Boĺshakov A.V., Shavyrin A.S., Kurskii Yu.A., Finet J.P., and Zelentsov S.V. Russ. Chem. Bull., Int. Ed. 53 (2004) 370-375
22. Sviridov S.I., Vasil'ev A.A., Sergovskaya N.L., Chirskaya M.V., and Shorshnev S.V. Tetrahedron 62 (2006) 2639-2647
23. Molander G.A., and Ham J. Org. Lett. 8 (2006) 2767-2770
24. Huang J., Macdonald S.J.F., and Harrity J.P.A. Chem. Commun. (2009) 436-438
25. Huang J., Macdonald S.J.F., Cooper A.W.J., Fisher G., and Harrity J.P.A. Tetrahedron Lett. 50 (2009) 5539-5541
26. Naumov M.I., Nuchev A.V., Sitnikov N.S., Malysheva Y.B., Shavyrin A.S., Beletskaya I.P., Gavryushin A.E., Combes S., and Fedorov A.Yu. Synthesis (2009) 1673-1682
27. Cho Y.A., Kim D.-S., Ahn H.R., Canturk B., Molander G.A., and Ham J. Org. Lett. 11 (2009) 4330-4333
28. Scrafton D.K., Taylor J.E., Mahon M.F., Fossey J.S., and James T.D. J. Org. Chem. 73 (2008) 2871-2874
29. Loren J.C., Krasiński A., Fokin V.V., and Sharpless K.B. Synlett (2005) 2847-2850
30. Jin S., Choudhary G., Cheng Y., Dai C., and Li M. Chem. Commun. (2009) 5251-5253
31. 11B NMR analysis was also consistent with this conclusion.
32. p-Tolylboronic acid (7) was synthesised as detailed, or purchased from Frontier Scientific Europe, product code T6078; see Supplementary data for full details.
33. Abbenante G., Le G.T., and Fairlie D.P. Chem. Commun. (2007) 4501-4503
34. After 3 h of irradiation (100 W Blak-Ray B100 UV lamp) the single-crystal X-ray structure was unchanged, further details are available in the Supplementary data.
35. Párkányi L., and Besenyei G. J. Mol. Struct. 691 (2004) 97-106
36. Chesterton A.K.S., Jenkinson S.F., Jones N.A., Fleet G.W.J., and Watkin D.J. Acta Crystallogr., Sect. E 62 (2006) o2983-o2985
37. Darses S., and Genet J.-P. Chem. Rev. 108 (2008) 288-325
38. For use of TMS-acetylene in CuAAC reactions and in situ de-silylation of the products, see:. Fletcher J.T., Walz S.E., and Keeney M.E. Tetrahedron Lett. 49 (2008) 7030-7032
39. For discussions on atom-economy and protecting groups, see:. Clark J.H. Green Chem. (1999) 1-8
40. Baran P.S., Maimone T.J., and Richter J.M. Nature 446 (2007) 404-408
41. Wu L.-Y., Xie Y.-X., Chen Z.-S., Niu Y.-N., and Liang Y.-M. Synlett (2009) 1453-1456
42. Though no particular efforts to scrub any hydroxides from the stream were made, no significant detrimental effect on the boronate was observed. A similar procedure was recently reported:. Jiang Y., Kuang C., and Yang Q. Synlett (2009) 3163-3166
43. Martin R., and Buchwald S.L. Acc. Chem. Res. 41 (2008) 1461-1473
44. 2O) was used to saturate the reaction solution. The reaction was run for 1 h at 60 °C, cooled and the process repeated once more. Full details are available in the Supplementary data.
45. For background discussion, see:. Tan D.S. Nat. Chem. Biol. 1 (2005) 74-84
46. For exemplary examples of the CuAAC in this context, see:. Manetsch R., Krasinski A., Radic Z., Raushel J., Taylor P., Sharpless K.B., and Kolb H.C. J. Am. Chem. Soc. 126 (2004) 12809-12818
47. Krasinski A., Radic Z., Manetsch R., Raushel J., Taylor P., Sharpless K.B., and Kolb H.C. J. Am. Chem. Soc. 127 (2005) 6686-6692
48. See the discussion of aryl chlorides in:. Cai C., Rivera N.R., Balsells J., Sidler R.R., McWilliams J.C., Shultz C.S., and Sun Y. Org. Lett. 8 (2006) 5161
49. Bunin B.A. Drug Discovery Today 8 (2003) 823-826
50. Wheless J.W., and Vazquez B. Epilepsy Curr. 10 (2010) 1-6