Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 18, Pages 3215-3222Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000525
Keywords
cascade reaction; Friedel-Crafts reaction; indoles; N-fused heterocycles; propargyl alcohol; silver
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Funding
- National Natural Science Foundation of China [20772098, 21072159]
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An efficient cascade methodology toward chemoselective synthesis of N-fused heterocycles including 9H-pyrrolo[1,2-a] indole, 3H-pyrrolo[1,2-a]indole and 1H-pyrrolo[1,2-a]indole derivatives has been developed. This transformation proceeds via a silver(I) triflate-catalyzed consecutive Friedel-Crafts reaction/N-C bond formation sequence between readily available propargyl alcohols and 3-substituted 1H-indoles. Not only is excellent chemoselectivity observed according to the substitution patterns of propargyl alcohols, but also the Lewis acid-catalyzed N-C bond formation process can be carried out under base- and ligand-free conditions.
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