Quinone diazides for olefin functionalization

Angewandte Chemie - International Edition

Volumn 53, Issue 52, 2014, Pages 14382-14386

  Dao, Hai T ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Olefin functionalization; Quinone diazide; Steroids; Triazenes

Indexed keywords

DIAZO COMPOUNDS; FUNCTIONALIZATIONS; MODERN TOOLS; OLEFIN CYCLOPROPANATION; ORGANIC SYNTHESIS; QUINONE DIAZIDE; STEROIDS; TRIAZENES;

OLEFINS;

ALKENES; AZIDES; QUINONES; STEROIDS;

CHEMICAL SYNTHESIS; CHEMISTRY; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; MOLECULAR CONFORMATION; STEREOISOMERISM;

ALKENES; AZIDES; CRYSTALLOGRAPHY, X-RAY; CYCLOADDITION REACTION; MOLECULAR CONFORMATION; QUINONES; STEREOISOMERISM; STEROIDS;

EID: 84919609013     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408022     Document Type: Article

References (53)

1. For books and book chapters, see V. V. Ershov, G. A. Nikiforvo, C. R. H. I. De Jonge, Studies in Organic Chemistry: Quinonediazides, Elsevier, Amsterdam, 1981;
2. A. G. Griesbeck, E. Zimmermann in Science of Synthesis, Vol. 28 (Ed.:A. G. Griesbeck), Thieme, Stuttgart, 2000, pp. 807-830.
3. H. Mori, I. Tando, H. Tanaka, Macromolecules 2010, 43, 7011-7020;
4. G. M.Wallraff,W. D. Hinsberg, Chem. Rev. 1999, 99, 1801-1822;
5. J. D. Olszewski, M. Marshalla, M. Sabat, R. J. Sundberg, J. Org. Chem. 1994, 59, 4285-4296;
6. M. J. Bouchet, A. Rendon, C. G. Wermuth, M. Goeldner, C. Hirth, J. Med. Chem. 1987, 30, 2222-2227;
7. T. Ohno, N. Martín, B. Knight, F. Wudl, T. Suzuki, H. Yu, J. Org. Chem. 1996, 61, 1306-1309;
8. B. Knight, N. Martín, T. Ohno, E. Ortí, C. Rovira, J. Veciana, J. Vidal-Gancedo, P. Viruela, R. Viruela, F. Wudl, J. Am. Chem. Soc. 1997, 119, 9871-9882;
9. M. Eckert-Maksić, D. Margetić, High Pressure Res. 2007, 27, 109-114.
10. G. F. Koser, W. H. Pirkle, J. Org. Chem. 1967, 32, 1992-1994;
11. J. C. Fleming, H. Shechter, J. Org. Chem. 1969, 34, 3962-3969;
12. S. Nakazawa, K. Hirakawa, S. Fujimori, K. Iwasaki, J. Chem. Soc. Perkin Trans. 1 1979, 2052-2056;
13. R. S.Ward, K. S. Thatcher, Tetrahedron Lett. 1981, 22, 4831-4834;
14. A. S. Kende, P. Hebeisen, P. J. Sanfilippo, B. H. Toder, J. Am. Chem. Soc. 1982, 104, 4244-4245;
15. G. A. Kraus, J. O. Nagy, J. DeLano, Tetrahedron 1985, 41, 2337-2340;
16. H. D. Becker, T. Elebring, J. Org. Chem. 1985, 50, 1319-1322;
17. A. S. Kende, P. Hebeisen, Tetrahedron Lett. 1985, 26, 3769-3772.
18. Metal-catalyzed cyclopropanations employing quinone diazides have been sporadically reported with a limited scope of quinone diazides and olefins: R. J. Sundberg, E. W. Baxter, Tetrahedron Lett. 1986, 27, 2687-2690;
19. R. J. Sundberg, E. W. Baxter, W. J. Pitts, R. Ahmed-Schofield, T. Nishiguchi, J. Org. Chem. 1988, 53, 5097-5107;
20. R. J. Sundberg,W. J. Pitts, J. Org. Chem. 1991, 56, 3048-3054;
21. D. L. Boger, P. Mesini, J. Am. Chem. Soc. 1994, 116, 11335-11348;
22. D. L. Boger, T. J. Jenkins, J. Am. Chem. Soc. 1996, 118, 8860-8870;
23. P. V. Murphy, T. J. O'Sullivan, N. W. Geraghty, J. Chem. Soc. Perkin Trans. 1 2000, 2109-2119.
24. For general cyclopropanations with carbenoids, see M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998;
25. M. P. Doyle, D. C. Forbes,Chem. Rev. 1998, 98, 911-936;
26. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050;
27. H. M. Davies, R. E. Beckwith, Chem. Rev. 2003, 103, 2861-2904;
28. J. L. Thompson, H. M. L. Davies, J. Am. Chem. Soc. 2007, 129, 6090-6091.
29. For selective two-electron-acceptor diazocarbonyl compounds and their application in Rh catalysis, see M. P. Doyle, S. B. Davies, W. Hu, Org. Lett. 2000, 2, 1145-1147;
30. O. Lifchits, D. Alberico, I. Zakharian, A. B. Charette, J. Org. Chem. 2008, 73, 6838-6840;
31. O. Lifchits, A. B. Charette, Org. Lett. 2008, 10, 2809-2812;
32. V. N. G. Lindsay, C. Nicolas, A. B. Charette, J. Am. Chem. Soc. 2011, 133, 8972-8981;
33. R. R. Nani, S. E. Reisman, J. Am. Chem. Soc. 2013, 135, 7304 - 7311; our classification is based on the 13C NMR chemical shift of the diazo groups (C=N2) : acceptor/acceptor diazocarbonyl compounds: ca. d = 80 ppm; monoacceptor and donor/acceptor diazocarbonyls: ca. d = 55 ppm; 1a : d = 79.5 ppm.
34. C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378-15379.
35. For a recent review, see M. R. Heinrich, Chem. Eur. J. 2009, 15, 820-833.
36. H. Ku, J. R. Barrio, J. Org. Chem. 1981, 46, 5239-5241;
37. D. B.Kimball, M. M.Haley, Angew. Chem. Int. Ed. 2002, 41, 3338 - 3351;
38. D. B. Kimball, M. M. Haley, Angew. Chem. 2002, 114, 3484-3498;
39. A.-F. Voica, A. Mendoza, W. R. Gutekunst, J. O. Fraga, P. S. Baran, Nat. Chem. 2012, 4, 629-635.
40. F. Gao, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 10961-10963.
41. S. E. Denmark, J. P. Germanas, Tetrahedron Lett. 1984, 25, 1231-1234;
42. K. Fukuzaki, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1984, 25, 3591-3594.
43. E. Piers, J. Renaud, J. Org. Chem. 1993, 58, 11-13.
44. K. Chen, Y. Ishihara, M. M. Galán, P. S. Baran, Tetrahedron 2010, 66, 4738-4744.
45. M. Schlosser, Organometallics in Synthesis: a Manual, Wiley, Hoboken, NJ, USA, 2002.
46. H. Ren, A. Krasovskiy, P. Knochel, Org. Lett. 2004, 6, 4215-4217.
47. S. Danishefsky, T. Kitahara, R. McKee, P. F. Schuda, J. Am. Chem. Soc. 1976, 98, 6715-6717;
48. 3 was critical for the C-C bond formation.
49. 0 and [Mo(CO)6] catalysis, see a) U. Mende, B. Radüchel, V. Skuballa, H. Vorbrüggen, Tetrahedron Lett. 1975, 16, 629-632;
50. M. P. Doyle, J. G. Davidson, J. Org. Chem. 1980, 45, 1538-1539; Co catalysis:
51. A. Nakamura, A. Konishi, Y. Tatsuno, S. Otsuka, J. Am. Chem. Soc. 1978, 100, 3443-3448.
52. 1H NMR studies revealed an unproductive coordination of the catalysts with the substrate.
53. [Rh2(OPiv)4] Gave 78%yield, and [Rh2(esp)2] Gave 80%overall yield in two steps from 21 to 23.