1
846
J. Liu et al. / Tetrahedron Letters 53 (2012) 1843–1846
3
-diketones in good to excellent yields (Table 2, entries 1–7). The
References and notes
substrates bearing electron-donating groups on their aromatic
rings reacted more easily even at room temperature for 6 h (Table
1
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1
0
amine (1l) and N-tosyl 1-(furan-2-yl)propan-1-amine (1m) did
not couple with acetyl acetone probably because of the unstability
of the carboncation. The use of 1j obtained a mixture of enol and
keto. The third amines, such as 1n and 1u, also proved to be suit-
able substrates to this reaction (Table 2, entry 14 and 15).
A variety of 1,3-dicarbonyl were tried for the cross-coupling
reaction with tosyl-activated benzylic and allylic amines (Table
(a) Yasuda, M.; Somyo, T.; Baba, A. Angew. Chem., Int. Ed. 2006, 45, 793–796; (b)
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1
3
). The cross-coupling reaction of 1a and 1e with most 1,3-dike-
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1
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4
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2
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5661; (c) Li, H.-H.; Dong, D.-J.; Tian, S.-K. Eur. J. Org. Chem. 2008, 3623; (d) Liu,
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Conclusions
In summary, we have successfully reported the benzylation and
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3
in the presence of Yb(OTf) . The cross-coupling reactions
3
proceeded through a cleavage of sp carbon–nitrogen bonds. The
advantages of this reaction are broad scope, high yield, mild condi-
tions, use of inexpensive catalyst, and simplicity of operation with
the only side product.
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Acknowledgments
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011, 52, 5104–5106.
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Price from Strem Chemicals: Yb(OTf) = $38.00/5 g, Sc(OTf)
This research was financially supported by the National Nature
Science Foundation of China (20672035) and Key Laboratory of
Organofluorine Chemistry, Shanghai Institute of Organic
Chemistry, Chinese Academy of Sciences.
1
8.
3
3
= $172.00/5 g.
9. Cui, X.-J.; Shi, F.; Tse, M.-K.; Goerdes, D.; Thurow, K.; Beller, M.; Deng, Y.-Q. Adv.
Synth. Catal. 2009, 351, 2949–2958.
1
0. Sun, W.-S.; Ma, X.-Z.; Hong, L.; Wang, R. J. Org. Chem. 2011, 76, 7826–7833.
11. This cross-coupling reaction is hard to proceed and rarely researched: Rueping,
M.; Nachtsheim, B.-J.; Kuenkel, A. Org. Lett. 2007, 9, 825–828.
Supplementary data
1
2. The examples of the similar products: Yuan, Y.; Feng, X.; Liu, X.-N.; Shi, Z.-Z.
Appl. Organomet. Chem. 2007, 21, 958–964.