Bio-and air-tolerant carbon-carbon bond formations via organometallic ruthenium catalysis

Collection of Czechoslovak Chemical Communications

Volumn 74, Issue 7-8, 2009, Pages 1023-1034

  Adriaenssens, Louis ^a   Severa, Lukáš ^a   Vávra, Jan ^a   Šálová, Tereza ^a   Hývl, Jakub ^a   Čfžková, Martina ^a   Pohl, Radek ^a   Šaman, David ^a   Teplý, Filip ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

2+2+2 cycloadditions; Alkene alkyne coupling; Alkynes; Arenes; C c coupling; Enyne diazocompound fusion; Helical structures; Helquat; Heterocycles; N heteroaromatic cations; Nitrogen based organic cations; Organometallic catalysis; Ruthenium

Indexed keywords

EID: 72149104328     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc2009053     Document Type: Article

References (68)

1. Corey E. J., Cheng X.-M.: The Logic of Chemical Synthesis. Wiley, New York 1995.
2. a) Crabtree R. H.: The Organometallic Chemistry of the Transition Metals, 4th ed. Wiley, Hoboken 2005;
3. Hegedus L. S.: Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed. University Science Books, Sausalito 1999.
4. For reviews on C-M bonds in nature, see: a) Kovacs J. A., Shoner S. C., Ellison J. J.: Science 1995, 270, 587;
5. Jaouen G. (Ed.): Bioorganometallics. Wiley-VCH, Weinheim 2006;
6. Beck W., Severin K.: Chem. Unserer Zeit 2002, 36, 356.
7. Non-catalytic applications of air-, water-and bio-compatible organometallics relevant to chemical biology are documented. For leading references, see: a) Allardyce C. S., Dorcier A., Scolaro C., Dyson P. J.: Appl. Organomet. Chem. 2005, 19, 1;
8. Yan Y. K., Melchart M., Habtemariam A., Sadler P. J.: Chem. Commun. 2005, 4764;
9. 3b'3c.
10. For reviews on artificial C-C bond formations catalyzed by late transition metals in air and water, see: a) Li C.-J.: Chem. Rev. 2005, 105, 3095;
11. Li C.-J., Chan T.-H.: Comprehensive Organic Reactions in Aqueous Media. Wiley, Hoboken 2007;
12. Lipshutz B. H., Ghorai S.: Aldrichimica Acta 2008, 41, 59.
13. For leading discussion on the catalytic aspect of bioorganometallic chemistry, see: Streu C., Meggers E.: Angew. Chem. Int. Ed. 2006, 45, 5645.
14. For an example of catalytic hydrogenation of membrane lipids in living systems, see: a) Vigh L., Joó F., Cséplö M.: Eur. J. Biochem. 1985, 146, 241;
15. Horváth I., Glatz A., Varvasovszki V., Török Z., Páli T., Balogh G., Kovács E., Nádasdi L., Benkö S., Joó F., Vigh L.: Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 3513.
16. For a note on CuAAC in human plasma, see: a) Rostovtsev V. V., Green L. G., Fokin V. V., Sharpless K. B.: Angew. Chem. Int. Ed. 2002, 41, 2596;
17. For CuAAC with living cells, see b) Link A. J., Tirrell D. A.: J. Am. Chem. Soc. 2003, 125, 11164.
18. a) Editorial address highlighting the need for non-coded reaction candidates amenable to integration with complex living cell environment, see: Sames D.: Chem. Eng. News 2001, 79, 276;
19. For recent overviews, see: b) Prescher J. A., Bertozzi C. R.: Nat. Chem. Biol. 2005, 1, 13;
20. Barglow K. T., Cravatt B. F.: Nat. Methods 2007, 4, 822;
21. Kurpiers T., Mootz H. D.: Angew. Chem. Int. Ed. 2009, 48, 1729.
22. For significant work towards this goal, see: a) Lin Y. A., Chalker J. M., Floyd N., Bernardes G. J., Davis B. G.: J. Am. Chem. Soc. 2008, 130, 9642;
23. Tilley S. D., Francis M. B.: J. Am. Chem. Soc. 2006, 128, 1080;
24. Antos J. M., Francis M. B.: J. Am. Chem. Soc. 2004, 126, 10256;
25. McFarland J. M., Francis M. B.: J. Am. Chem. Soc. 2005, 127, 13490;
26. Mortell K. H., Gingras M., Kiessling L. L.: J. Am. Chem. Soc. 1994, 116, 12053;
27. Dibowski H., Schmidtchen F. P.: Angew. Chem. Int. Ed. 1998, 37, 476;
28. Bong D. T., Ghadiri M. R.: Org. Lett. 2001, 3, 2509;
29. Ojida A., Tsutsumi H., Kasagi N., Hamachi I.: Tetrahedron Lett. 2005, 46, 3301;
30. i) Liebeskind L. S., Yang H.; Li H.: Angew. Chem. Int. Ed. 2009, 48, 1417;
31. For overview, see: j) Antos J. M., Francis M. B.: Curr. Opin. Chem. Biol. 2006, 10, 253, and references therein.
32. 12 is known to catalyze C-C bond formations proceeding via organometallic pathways of radical character, see a) Butler P. A., Kräutler B.: Top. Organomet. Chem. 2006, 17, 1;
33. Specifically, anaerobic archebacteria employ methylcobaltamin in conjuction with nickel organometallics in an acetyl-coenzyme A synthasecatalyzed coupling of carbon monoxide with a methyl group to construct a C-C bond in an acetyl moiety, see: b) Ragsdale S. W.: Chem. Rev. 2006, 106, 3317;
34. A related catalytic pathway, involving organometallics under anaerobic aqueous conditions, has been proposed to be the primordial initiation reaction for a chemoautotrophic origin of life, see: c) Huber C., Wächtershä user G.: Science 1997, 276, 245;
35. Crabtree R. H.: Science 1997, 276, 222.
36. For pioneering report, see: Agard N. J., Prescher J. A., Bertozzi C. R.: J. Am. Chem. Soc. 2004, 126, 15046;
37. For an overview, see: Agard N. J., Baskin J. M., Prescher J. A., Lo A., Bertozzi C. R.: ACS Chem. Biol. 2006, 1, 644.
38. a) Wang Q., Chan T. R., Hilgraf R., Fokin V. V., Sharpless K. B., Finn M. G.: J. Am. Chem. Soc. 2003, 125, 3192;
39. Speers A. E., Cravatt B. F.: Chem. Biol. 2004, 11, 535;
40. 8.
41. For an overview of the versatility of catalyst 1, see: a) Dérien S., Dixneuf P. H.: J. Organomet. Chem. 2004, 689, 1382;
42. Trost B. M., Frederiksen M. U., Rudd M. T.: Angew. Chem. Int. Ed. 2005, 44, 6630, and references therein.
43. For an initial report on this process under anhydrous conditions and inert atmosphere, see: Yamamoto Y., Arakawa T., Ogawa R., Itoh K.: J. Am. Chem. Soc. 2003, 125, 12143.
44. 2, see: a) Severa L., VáVra J., Kohoutová A., Číž ková M., Šálová T., Hývi J., Šaman D., Pohl R., Adriaenssens L., Teplý F.: Tetrahedron Lett. 2009, 50, 4526;
45. Yokota T., Sakurai Y., Sakaguchi S., Ishii Y.: Tetrahedron Lett. 1997, 38, 3923;
46. Ardizzoia G. A., Brenna S., LaMonica G., Maspero A., Masciocchi N.: J. Organomet. Chem. 2002, 649, 173;
47. Geny A., Agenet N., Iannazzo L., Malacria M., Aubert C., Gandon V.: Angew. Chem. Int. Ed. 2009, 48, 1810;
48. 25
49. 2 atmosphere at 75 °C, see: Cadierno V., García-Garrido S. E., Gimeno J.: J. Am. Chem. Soc. 2006, 128, 15094.
50. For an initial report on this process under anhydrous conditions and inert atmosphere, see: Yamamoto Y., Kinpara K., Ogawa R., Nishiyama H., Itoh K.: Chem.-Eur. J. 2006, 12, 5618.
51. Šálová T.: M. S. Thesis. Charles University, Prague 2008.
52. For an initial report on this process under inert atmosphere in presence of water, see: Dérien S., Jan D., Dixneuf P. H.: Tetrahedron 1996, 52, 5511.
53. For a note on oxygen-and moisture-tolerance of Ru-catalyzed alkene-alkyne coupling, see: Trost B. M., Pinkerton A. B., Toste F. D., Sperrle M.: J. Am. Chem. Soc. 2001, 123, 12504;
54. 14b;
55. 2O-compatibility of this process remains, to the best of our knowledge, unexplored.
56. For a recent example of aldehyde follow-up reactivity, see: Angelov T., Guainazzi A., Schärer O. D.: Org. Lett. 2009, 11, 661.
57. This process has been recently described to proceed rapidly in presence of water under inert atmosphere, see: Monnier F., Vovard-Le Bray C., Castillo D., Aubert V., Dérien S., Dixneuf P. H., Toupet L., Lenco A., Mealli C.: J. Am. Chem. Soc. 2007, 129, 6037.
58. Preliminary NMR investigation suggests 13 was obtained as a racemate.
59. Adriaenssens L., Severa L., Šálová T., Císařová I., Pohl R., Šaman D., Rocha S. V., Finney N. S., Pospíšil L., Slavíček P., Teplý F.: Chem.-Eur. J. 2009, 15, 1072.
60. 1H NMR with comparison to DMSO as an internal standard. Details in Electronic Supplementary Data section.
61. Details in Electronic Supplementary Data accompanying this article.
62. a) Williams D. S., Atilla G. E., Bregman H., Arzoumanian A., Klein P. S., Meggers E.: Angew. Chem. Int. Ed. 2005, 44, 1984;
63. For a review, see: b) Melchart M., Sadler P. J. in: Bioorganometallics (G. Jaouen, Ed.), p. 39. Wiley-VCH, Weinheim 2006;
64. 4a, 4b; For a recent account, see: c) Gossens C., Tavernelli I., Rothlisberger U.: J. Am. Chem. Soc. 2008, 130, 10921;
65. For excellent overview, see: d) Meggers E.: Curr. Opin. Chem. Biol. 2007, 11, 287.
66. Amabilino D. B., Ashton P. R., Reder A. S., Spencer N., Stoddart J. F.: Angew. Chem., Int. Ed. Engl. 1994, 33, 1286.
67. Gibson S. E., Kaufmann K. A. C., Haycock P. R., White A. J. P., Hardick D. J., Tozer M. J.: Organometallics 2007, 26, 1578.
68. Monnier F., Castillo D., Dérien S., Toupet L., Dixneuf P. H.: Angew. Chem. Int. Ed. 2003, 42, 5474.