Organic Letters
Letter
(9) [2,3]-Wittig rearraangement: (a) West, T. H.; Spoehrle, S. S. M.;
Kasten, K.; Taylor, J. E.; Smith, A. D. ACS Catal. 2015, 5, 7446−7479.
(b) Davies, P. W.; Albrecht, S. J. C. Chem. Commun. 2008, 238.
(c) Davies, P. W.; Albrecht, S. J. C. Angew. Chem., Int. Ed. 2009, 48,
8372−8375.
(10) 1,n-Sulfur migration in gold catalysis: (a) Peng, L.; Zhang, X.;
Zhang, S.; Wang, J. J. Org. Chem. 2007, 72, 1192. (b) Zhao, X.; Zhong,
Z.; Peng, P.; Zhang, W.; Wang, J. Chem. Commun. 2009, 2535.
(11) We examined the oxidations of thioalkyne with 8-methylquino-
line N-oxides; the reaction intermediates were elucidated to be ketenes
instead of α-oxo gold carbenes. In other words, this system serves as the
first example to use alkynes as ketene precursors.
bridge Crystallographic Data Centre, 12 Union Road, Cam-
bridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(12) Nucleophilic activations of quinoline N-oxide typically proceed
through a 3,3-sigmatropic shift; see selected examples: (a) Chen, Z.-S.;
Yang, F.; Ling, H.; Li, M.; Gao, J.-M.; Ji, K. Org. Lett. 2016, 18, 5828.
(b) Zhang, B.; Huang, L.; Yin, S.; Li, X.; Xu, T.; Zhuang, B.; Wang, T.;
Zhang, Z.; Hashmi, A. S. K. Org. Lett. 2017, 19, 4327. (c) Han, Y.-P.; Li,
X.-S.; Zhu, X.-Y.; Li, M.; Zhou, L.; Song, X.-R.; Liang, Y.-M. J. Org.
Chem. 2017, 82, 1697. (d) Wang, Y.; Zhang, L. Synthesis 2015, 47, 289.
(e) Bhunia, S.; Chang, C.-J.; Liu, R.-S. Org. Lett. 2012, 14, 5522.
(f) Karad, S. N.; Liu, R.-S. Angew. Chem., Int. Ed. 2014, 53, 5444.
(13) The very high cost and low concentration (3 wt %) of aqueous
18O-containing H2O2 (90% 18O, USD 2,140/1g, Sigma-Aldrich) did
not allow us to prepare 18O-containing 8-methylquinoline oxide 2a. In
our proposed mechanism, this 18O-containing sample is expected to
give a positive result because it generates water. One reviewer suggests a
mechanism as depicted below with this N-oxide as a nucleophile; we
cannot exclude this process as a competitive reaction.
We thank the Ministry of Education (MOE 106N506CE1) and
the Ministry of Science and Technology (MOST 107-3017-F-
007-002), Taiwan, for financial support of this work.
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