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Division of Chemistry, Graduate School of Science, Hokkaido University, N10 W8, Sapporo 060-0810, Japan
E-mail: oguri@sci.hokudai.ac.jp
; Fax: +81-11-706-3448
; Tel: +81-11-706-3429
Org. Biomol. Chem., 2012,10, 4236-4242
DOI:
10.1039/C2OB25236H
Received
01 Feb 2012,
Accepted
22 Mar 2012
First published online
23 Mar 2012
We have developed a unique catalytic protocol for direct gem-vinylation of tryptamine derivatives employing Hg(OTf)2 as the optimum catalyst. The intermolecular vinylations with a series of aromatic acetylenes proceeded under ambient temperature at the C2 positions of indoles with high functional group tolerance. Based on the mechanistic insights, we further developed the tandem reactions successfully constructing a quaternary center.
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Organic & Biomolecular Chemistry
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