Hexyl triazabutadiene as a potent alkylating agent

Diana C. Knyazeva, Flora W. Kimani, Jean Laurent Blanche, John C Jewett

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Alkyl diazonium ions are among the most reactive alkylating agents in the synthetic chemists’ arsenal. That said, there are precious few methods by which one can selectively and safely utilize this chemistry. Herein, we show the use of a bench stable hexyl triazabutadiene as a source of reactive diazonium ions that undergo substitution chemistry with weak nucleophiles, such as carboxylates and even sulfonates. In the absence of a nucleophile, elimination was observed to occur. To overcome issues stemming from side-product inhibition of the reaction, we show that the triazabutadiene can be pre-activated with tosyl isocyanate.

Original languageEnglish (US)
Pages (from-to)2700-2702
Number of pages3
JournalTetrahedron Letters
Volume58
Issue number28
DOIs
StatePublished - Jul 12 2017

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Nucleophiles
Alkylating Agents
Ions
Arsenals
Isocyanates
Substitution reactions

Keywords

  • Alkyl diazonium ion
  • Alkylating reagent
  • Brønsted-Lowry acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Hexyl triazabutadiene as a potent alkylating agent. / Knyazeva, Diana C.; Kimani, Flora W.; Blanche, Jean Laurent; Jewett, John C.

In: Tetrahedron Letters, Vol. 58, No. 28, 12.07.2017, p. 2700-2702.

Research output: Contribution to journalArticle

Knyazeva, Diana C. ; Kimani, Flora W. ; Blanche, Jean Laurent ; Jewett, John C. / Hexyl triazabutadiene as a potent alkylating agent. In: Tetrahedron Letters. 2017 ; Vol. 58, No. 28. pp. 2700-2702.
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