Organic Letters
Letter
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In summary, we developed an efficient and concise protocol
for direct alkynylation of aliphatic organohalides with terminal
alkynes via Cu-catalysis by introducing a directing strategy. This
method exhibits a broad substrate scope with respect to both
terminal alkynes and alkyl halides, and even tosylates and
mesylates. Indeed, this is the first successful protocol for
alkynylation of alkyl chlorides in the absence of any additives.
Such a coupling prefers alkyl chlorides over other halides/
peusudohalides. Preliminary mechanistic studies ruled out a
radical pathway. Our next challenge is to extend the reaction to
more sterically hindered tertiary organohalides.
ASSOCIATED CONTENT
* Supporting Information
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S
The Supporting Information is available free of charge on the
Experimental details, spectroscopic data for all new
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(8) Vechorkin, O.; Barmaz, D.; Proust, V.; Hu, X. L. J. Am. Chem. Soc.
2009, 131, 12078.
AUTHOR INFORMATION
Corresponding Author
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́
(9) Perez García, P. M.; Ren; Scopelliti, P. R.; Hu, X. ACS Catal.
Notes
2015, 5, 1164.
The authors declare no competing financial interest.
(10) Yi, J.; Lu, X.; Sun, Y.-Y.; Xiao, B.; Liu, L. Angew. Chem., Int. Ed.
2013, 52, 12409.
(11) Liu, W.; Li, L.; Li, C.-J. Nat. Commun. 2015, 6, DOI: 10.1038/
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11726. (b) Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52,
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Chem. Front. 2015, 2, 1107. (d) Yu, D.-G.; Li, B.-J.; Shi, Z.-J.
Tetrahedron 2012, 68, 5130.
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(b) Wang, J.; Zuo, S.; Chen, W.; Zhang, X.; Tan, K.; Tian, Y.; Wang, J.
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2005, 127, 13154.
ACKNOWLEDGMENTS
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Support of this work by the “973” Project from the MOST of
China (2013CB228102, 2015CB856600), NSFC (No.
21332001). We gratefully thank Prof. Jianbo Wang’s group
for supplying the 1-bromo-4-ethynylbenzene (2n).
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