Trans- and cis-selective Lewis acid catalyzed hydrogermylation of alkynes

Todd Schwier, Vladimir Gevorgyan

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

(Chemical Equation Presented) The first examples of Lewis acid catalyzed hydrogermylation of alkynes have been demonstrated. It was found that this method has much higher functional group compatibility compared to the known Lewis acid catalyzed hydrosilylation and hydrostannation reactions. Remarkably, the stereochemical outcome of this hydrogermylation reaction depends on the nature of the alkyne used: proceeding via a trans-addition pathway with simple alkynes and cis-addition with propiolates. Mechanistic studies strongly support the proposed rationale on the origins of cis-selectivity in the hydrogermylation of activated alkynes.

Original languageEnglish (US)
Pages (from-to)5191-5194
Number of pages4
JournalOrganic Letters
Volume7
Issue number23
DOIs
StatePublished - Nov 10 2005
Externally publishedYes

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Lewis Acids
Alkynes
alkynes
acids
Hydrosilylation
compatibility
Functional groups
selectivity

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Trans- and cis-selective Lewis acid catalyzed hydrogermylation of alkynes. / Schwier, Todd; Gevorgyan, Vladimir.

In: Organic Letters, Vol. 7, No. 23, 10.11.2005, p. 5191-5194.

Research output: Contribution to journalArticle

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