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substituted naphthalene derivatives from simple aromatic 1,5-enyne
substrates. In addition to the development of novel methodology the
mechanism of this cascade reaction has also been studied based on
intermediates isolated through deuterium labeling experiments.
We gratefully acknowledge financial support from the
National Natural Science Foundation of China (Grant No.
21202103), program for innovative research team of the Minis-
try of Education and program for Liaoning innovative research
team in university, and Shenyang Pharmaceutical University.
We also thank Professor Ping Gong for facilities support.
Notes and references
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Scheme 3 Deuterium labeling experiments. aThe 1H NMR of the reaction of
1
1c in CH3OH (or CD3OH). bThe H NMR of the reaction of 1c in CD3OD (or
CH3OD). cThe 1H NMR of the reaction of 1c (or 6c) in CH3OH. dThe 1H NMR of
the reaction of 1c (or 6c) in CD3OD. eThe 1H NMR of the reaction of 1c (or 6c) in
CH3OD. fThe 1H NMR of the reaction of 1c (or 6c) in CD3OH.
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Scheme 4 Proposed mechanism of the cascade reaction.
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coordinated with the cationic gold catalyst to induce the second
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nol spontaneously15 to provide the naphthalene 6c after deauration 13 A. S. K. Hashmi, S. Schafer, M. Wolfle, C. D. Gil, P. Fischer, A. Laguna,
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M. C. Blanco and M. C. Gimeno, Angew. Chem., Int. Ed., 2007, 46, 6184.
of the intermediate 1c-2.
14 K. Graf, P. D. Hindenberg, Y. Tokimizu, S. Naoe, M. Rudolph,
In summary, we have developed a novel approach to the con-
F. Rominger, H. Ohno and A. S. K. Hashmi, ChemCatChem, 2014, 6, 199.
struction of naphthalene derivatives using [(NHC)AuI]-based catalytic 15 Examples of the elimination of methanol and silanols for the
formation of an aromatic systems, see (a) M. G. Christiane and
system and cascade cyclization strategy, which provides a unique
example of the nucleophile ratios on changing pathways of
Au(I)-catalyzed cyclization. It allows the preparation of a variety of
¨
B. Louis, Org. Lett., 2006, 8, 5905; (b) A. S. K. Hashmi and M. Wolfle,
Tetrahedron, 2009, 65, 9021; (c) A. S. K. Hashmi, W. Yang and
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