Journal
HETEROCYCLES
Volume 56, Issue 1-2, Pages 525-529Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-01-S(K)31
Keywords
Heck reaction; chloranil; palladium acetate; oxidant
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Palladium-catalyzed direct activation of carbon-hydrogen bond at C-3 position of 4-bromo-1-tosylindole (1) was investigated. The reaction of 1 with ethyl acrylate (4) in the presence of 0.1 eq. of Pd(OAc)(2) and MnO2-Cu(OAc)(2)-O-2 system afforded C-3 vinylated product (5) in 52% yield, and by-products (6 and 7) that were formed by the Michael addition of AcOH or H2O to 5, were obtained in 17% and 7% yields respectively.
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