DOI: 10.1039/C3CC44435J
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respectively.
The mechanism for the present catalytic reaction is not yet
clear. Based on the present results and the known copper
chemistry in literature,5,13 we propose a possible pathway for this
CuI-catalyzed isatin formation as shown in Scheme 2. Under the
reaction conditions, 2-aminoglyoxal A is expected to be formed
from 2-aminoaryl methyl ketone 1.5b The intramolecular addition
of amino group to the aldehyde group of glyoxal A results in the
formation of 2-hydroxyindolin-3-one derivative B which is
5
55
60
65
70
75
80
10 further oxidized by Cu(I)/O2 to form the final product 2.5b,13,15
4
5
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6
Scheme 2
7
In conclusion, we have successfully developed a convenient
Cu(I)-catalyzed intramolecualr oxidative CH amination reaction
15 of 2-aminoacetophenones for the synthesis of isatins. This
reaction allows the synthesis of various N-alkyl or aryl
substituted isatins in good to excellent yields. Further application
of this method to other substrates and the detailed mechanistic
investigation are in progress.
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We thank the National Science Council of Republic of China
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Notes and references
*Department of Chemistry, National Tsing Hua University, Hsinchu
25 30013, Taiwan Fax: 886-3-5724698; Tel: 886-3-5721454; E-mail:
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