Organic Letters
Letter
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures along with characterizing data
and copies of NMR spectra (PDF)
Accession Codes
mentary crystallographic data for this paper. These data can be
contacting The Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
Corresponding Author
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ORCID
Notes
(5) Basavaiah, D.; Devendar, B.; Lenin, D. V.; Satyanarayana, T.
Synlett 2009, 2009, 411.
(6) For selected reviews on diazo compounds, see: (a) Zhao, X.;
Zhang, Y.; Wang, J. Chem. Commun. 2012, 48, 10162. (b) Guo, X.;
Hu, W. Acc. Chem. Res. 2013, 46, 2427. (c) Ford, A.; Miel, H.; Ring,
A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Chem. Rev. 2015,
115, 9981. (d) Candeias, N. R.; Paterna, R.; Gois, P. M. P. Chem. Rev.
2016, 116, 2937. (e) Liu, L.; Zhang, J. Chem. Soc. Rev. 2016, 45, 506.
(f) Ciszewski, Łu. W.; Rybicka-Jasinska, K.; Gryko, D. Org. Biomol.
Chem. 2019, 17, 432.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We thank the Natural Science Foundation of Guangdong
Province (No. 2018A030310680) and the Research Founda-
tion of Department of Education of Guangdong Province (No.
2017KQNCX204, 2018KTSCX236) for financial support.
(7) Padwa, A.; Austin, D. J.; Precedo, L.; Zhi, L. J. Org. Chem. 1993,
58, 1144.
(8) (a) Day, J.; McKeever-Abbas, B.; Dowden, J. Angew. Chem., Int.
Ed. 2016, 55, 5809. For an asymmetric version, see: (b) Zhang, D.;
Lin, L.; Yang, J.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2018, 57,
12323.
(9) Douglas, T.; Pordea, A.; Dowden, J. Org. Lett. 2017, 19, 6396.
(10) Chen, R.; Zhao, Y.; Sun, H.; Shao, Y.; Xu, Y.; Ma, M.; Ma, L.;
Wan, X. J. Org. Chem. 2017, 82, 9291.
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(12) Both adding sequence of starting materials and adding method
are critical for this reaction. General procedure: A solution of alkyne 2
(0.24 mmol) and diazo compound 3 (0.3 mmol) in 1.0 mL of xylenes
was added into a solution of quinoline 1 (0.2 mmol) and catalyst (2−
10 mol %) in 1.0 mL of xylenes via an automatic syringe pump over
60 min at rt under dry argon atmosphere. Then the resulting solution
was stirred at rt for 8 h (monitored by TLC). Please see the
D
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