Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 18, Pages 3107-3112Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900609
Keywords
alkynes; copper; cyclization; halogenation; nitrogen heterocycles
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Funding
- The National Basic Research Program of China [2006CB806105]
- National Natural Sciences Foundation of China [20472099]
- Chinese Academy of Sciences
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A convenient and efficient method for the synthesis of 3-haloindoles has been developed. Both 3-chloro- and 3-bromoindole derivatives can be obtained in high yields by the reaction of N-electron-withdrawing group-substituted 2-alkynylanilines with cupric halide in dimethyl sulfoxide (DMSO) within a short period of time. Investigation of the reaction mechanism reveals that two equivalents of cupric halide are necessary.
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