4
12. (a)Swamy, V. M.; Ilankumaran, P.; Chandrasekaran, S. Synlett
1997, 513; (b) Sinha, S.; Ilankumaran, P.; Chandrasekaran, S.
Tetrahedron Lett. 1999, 40, 771.
On the basis of the above results, the method was applied to
the N-propargyl cleavage of acetyl amides (Table 3, entries 10-
16). Gratifyingly, substrate 3j afforded 4j in 93% yield (Entry
10). As expected, substrates including electron-rich groups and
halogen groups reacted with good to excellent yields (Entries 11-
14). However, a strongly electron-deficient group (NO2-) at the
meta- or para-position of the aromatic ring gave lower yields,
and the products were formed in 34% and 15% yield,
respectively (Entries 15 and 16). These results indicated that the
reaction was less sensitive to steric effects of the aryl group
substituent, while it was more sensitive to the electronic effect.
In conclusion, we have developed a convenient method for the
selective cleavage of N-propargyl groups from sulfonamides and
amides under ruthenium catalysis. The reaction tolerates a range
of functional groups, and the desired products were obtained in
low to excellent yields (10-95%).
13. Mereyala, H. B.; Gurrala, S. R.; Mohan, S. K. Tetrahedron, 1999,
55, 11331.
Acknowledgments
We are gratefully acknowledged for financial support from the
National Natural Science Foundation of China (Nos. 21402116,
21502111), the Key Scientific and Technological Project of
Henan Province (Nos. 172102210099 and 182102210483) and
the Key Science Research of Education Committee in Henan
Province (No. 15A150072).
References and notes
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