Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles

Ilya V. Seregin, Vladimir Gevorgyan

Research output: Contribution to journalArticle

224 Citations (Scopus)

Abstract

An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.

Original languageEnglish (US)
Pages (from-to)12050-12051
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number37
DOIs
StatePublished - Sep 20 2006
Externally publishedYes

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Germanium
Pyrroles
Alkynes
Tin
Silicon
Gold
Isomerization
Hydrogen
Catalysts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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abstract = "An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.",
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AU - Seregin, Ilya V.

AU - Gevorgyan, Vladimir

PY - 2006/9/20

Y1 - 2006/9/20

N2 - An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.

AB - An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.

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