Double C-H activation during functionalization of phenyl(methyl)ketene on iridium(I) using alkynes. Synthesis of 1,4-dien-3-ones

Journal of the American Chemical Society

Volumn 126, Issue 29, 2004, Pages 8866-8867

  Grotjahn, Douglas B ^a   Hoerter, Justin M ^a   Hubbard, John L ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIEN 3 ONE DERIVATIVE; ALKYNE; CARBON; HYDROGEN; IRIDIUM; KETENE DERIVATIVE; LIGAND; PHENYL(METHYL)KETENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; HEATING; HYDROGEN BOND; INFRARED SPECTROSCOPY; METAL BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; THERMAL ANALYSIS; X RAY DIFFRACTION;

EID: 3242813668     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048489+     Document Type: Article

References (36)

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14. For leading references to single C-H activation followed by alkene or alkyne insertion, see: Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770. Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506-7507.
15. For leading references to single C-H activation followed by alkene or alkyne insertion, see: Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770. Lail, M.; Arrowood, B. N.; Gunnoe, T. B. J. Am. Chem. Soc. 2003, 125, 7506-7507.
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21. If the ketene was added neat, or if there was excess phosphine or metal precursor, lower yields of ketene complex were obtained; observation of insoluble white opaque material suggested that the ketene had polymerized.
22. See Supporting Information for full details.
23. Grotjahn, D. B.; Collins, L. S. B.; Wolpert, M.; Lo, H. C.; Bikzhanova, G. A.; Combs, D.; Hubbard, J. L. J. Am. Chem. Soc. 2001, 123, 8260-8270.
24. Grotjahn, D. B.; Lo, H. C. Organometallics 1995, 14, 5463-5465, footnote 16.
25. 3, wR = 9.36% for 5687 observed reflections, wR = 9.60% for 6037 independent reflections, GOF = 1.079.
26. 6 produced CO complex 4 and styrene (each ≥98% yield).
27. 3, wR = 9.85% for 5853 observed reflections, wR = 22.25% for 5887 independent reflections, GOF = 1.039.
28. Similar unusual bond lengths have been noted in other, related species. See, for example: Bleeke, J. R.; New, P. R.; Blanchard, J. M. B.; Haile, T.; Beatty, A. M. Organometallics 1995, 14, 5127-5137 and ref 6 therein.
29. 2.4c
30. We previously reported the photochemical activation of the methyl group in 1, which leads to a hydride related to A but lacking the alkyne. See footnote 26 of ref 4b.
31. The ratio of these products changed somewhat over time,7 in a reaction which was slightly accelerated by addition of 2-phenylpropionic acid, a likely product of hydrolysis of some phenyl(methyl)ketene. Thus, the most likely isomerization mechanism involves proton catalysis, though see also: Huggins, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1979, 101, 4410-4412. Alexander, J. J. In The Chemistry of the Metal-Carbon Bond, Vol. 2; Hartley, F., Patai, S., Eds.; Wiley: New York, 1985; pp 339-400.
32. The ratio of these products changed somewhat over time,7 in a reaction which was slightly accelerated by addition of 2-phenylpropionic acid, a likely product of hydrolysis of some phenyl(methyl)ketene. Thus, the most likely isomerization mechanism involves proton catalysis, though see also: Huggins, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1979, 101, 4410-4412. Alexander, J. J. In The Chemistry of the Metal-Carbon Bond, Vol. 2; Hartley, F., Patai, S., Eds.; Wiley: New York, 1985; pp 339-400.
33. An example of dienone metalation: Tully, W.; Main, L.; Nicholson, B. K. J. Organomet. Chem., 2001, 633, 162-172.
34. Examples: Kjeldsen, G.; Knudsen, J. S.; Ravn-Petersen, L. S.; Torssell, K. B. G. Tetrahedron, 1983, 39, 2237-2239. Giese, S.; West, F. G. Tetrahedron Lett. 1998, 39, 8393-8396. Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.
35. Examples: Kjeldsen, G.; Knudsen, J. S.; Ravn-Petersen, L. S.; Torssell, K. B. G. Tetrahedron, 1983, 39, 2237-2239. Giese, S.; West, F. G. Tetrahedron Lett. 1998, 39, 8393-8396. Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.
36. Examples: Kjeldsen, G.; Knudsen, J. S.; Ravn-Petersen, L. S.; Torssell, K. B. G. Tetrahedron, 1983, 39, 2237-2239. Giese, S.; West, F. G. Tetrahedron Lett. 1998, 39, 8393-8396. Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.