Gold-catalyzed intramolecular [3 + 2]-cycloaddition of arenyne-yne functionalities

Journal of the American Chemical Society

Volumn 128, Issue 35, 2006, Pages 11372-11373

  Lian, Jian Jou ^a   Chen, Po Chiang ^a   Lin, Yau Ping ^a   Ting, Hao Chun ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ESTER; GOLD DERIVATIVE; KETONE; METAL COMPLEX; PALLADIUM COMPLEX; PLATINUM DERIVATIVE; SILVER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; CYCLOADDITION; X RAY DIFFRACTION;

EID: 33748352754     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0643826     Document Type: Article

References (26)

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2. (b) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776 and references therein.
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5. (e) González, J. J.; Francesch, A.; Cárdenas, D. J.; Echavarren, A. M. J. Org. Chem. 1998, 63, 2854.
6. For metal-catalyzed [4 + 2]-cycloadditions of enynes with alkynes, see selected reviews and the most recent paper: (a) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2265.
7. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
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9. Danheiser reported a [4 + 2]-cycloaddition of ynones-ynes, which undergoes thermal rearrangement to form a 3-alkenylfuran species. Wills, M. S. B.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9378.
10. Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178.
11. 6 as π-alkyne activators, see ref 4 and: (a) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
12. (b) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
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19. 4 (5%) and Aliquat 336 were reported to catalyze the transformation of species 1 into [3 + 2]-cycloadduct 2 in 26% yield. See: Badrieh, Y.; Blum, J.; Vollhardt, K. P. C. J. Mol. Catal. 1990, 60, 323.
20. 3OTf and diyne 13 in 1,4-dioxane (100 °C, 24 h) did not form a gold mirror in this example.
21. 1H NOE map of key compounds and X-ray data of cycloadduct 18 are provided in Supporting Information.
22. In this case, the use of methanol (1.0 equiv) led to formation of byproduct via alkyne hydration, and the desired cyclized 2 was obtained in 51% yield. Water acts an inhibitor for this catalytic reaction.
23. 6-based catalysis. The inhibition role of 2,6-lutidine is thought to intercept the proton to avoid the formation of intermediate C.
24. As suggested by one reviewer, the present data also support an alternative reaction mechanism as depicted below. (Diagram presented).
25. A proposed mechanism to rationalize formation of a [4 + 2]-cycloadduct by Au(I) species is provided in Supporting Information: see Scheme S-1.
26. 6 catalyst (0 °C, 5 h). Following their reported procedures, we still obtained [3 + 2]-cycloadducts 18 and 22 in 85 and 67% yields, respectively, from diynes 5 and 9 in addition to [4 + 2]-cycloadducts C (3-5%). The X-ray structure of cycloadduct 18 supports our structural assignment. See: Shibata, T.; Fujiwara, R.; Takano, D. Synlett. 2005, 2062. (Diagram presented).