Silver-catalyzed Glaser coupling of alkynes
Table 4. Ag-catalyzed Glaser coupling with various alkynesa
Acknowledgements
This work was financially supported by the National Natural Science
Foundation of China (grant nos. 21164004 and 30840050), the
Youth Fund of Natural Science of Hebei North University (grant
no. Q201101) and Zhangjiakou Science and Technology Research
and Development Program (grant no. 1321022B) which is greatly
appreciated.
Entry
R
Yield(%)b
1
p-CH3O–C6H4
p-C2H5–C6H4
p-C3H7–C6H4
C6H5
97
92
95
94
89
90
96
86
78
67
63
87
75
69
68
61
2
3
4
References
5
p-F–C6H4
6
p-Ac–C6H4
p-CH3–C6H4
m-CH3–C6H4
o-CH3–C6H4
1-C10H7
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n-C6H13
n-C8H17
n-C10H21
aReaction conditions: alkyne (1.0 mmol), AgNO3 (0.05 mmol), PPh3
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In summary, we have developed a simple and unique silver nitrate-
catalyzed oxidative Glaser coupling of various alkynes to synthesize
the corresponding 1,3-diyne products. The silver(I)-catalyzed Glaser
coupling reaction is significantly dependent upon reaction condi-
tions such as ligand, solvent and base as well as on the silver catalyst.
Both aromatic and aliphatic propiolic acids can be used as the cou-
pling substrates for the Ag(I) catalytic system. The search for addi-
tional applications for other alkynes is under way in our laboratory.
Supporting Information
Additional supporting information may be found in the online ver-
sion of this article at the publisher’s web-site.
Appl. Organometal. Chem. 2015, 29, 231–233
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