Hg(OTf)2-catalyzed direct vinylation of tryptamines and versatile applications for tandem reactions

Haruki Mizoguchi; Hideaki Oikawa; Hiroki Oguri

doi:10.1039/c2ob25236h

Hg(OTf)₂-catalyzed direct vinylation of tryptamines and versatile applications for tandem reactions

Haruki Mizoguchi, Hideaki Oikawa, Hiroki Oguri

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4236-4242
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	21
DOIs	https://doi.org/10.1039/c2ob25236h
Publication status	Published - Jun 7 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c2ob25236h

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abstract = "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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AU - Mizoguchi, Haruki

AU - Oikawa, Hideaki

AU - Oguri, Hiroki

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Y1 - 2012/6/7

N2 - 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.

AB - 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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ER -

Hg(OTf)₂-catalyzed direct vinylation of tryptamines and versatile applications for tandem reactions

Abstract

ASJC Scopus subject areas

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