Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent

William Kerr, Angus J Morrison, Marek Pazicky, Tina Weber

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Bismesitylmagnesium has been shown to successfully mediate the Shapiro reaction. A range of tosylhydrazones has been subjected to the developed system, which furnishes exceptionally high incorporation of the introduced electrophiles and good yields of the functionalised styrenes. At conveniently accessible temperatures and with a comparably small excess of base reagent, this protocol offers an efficient alternative to the lithium-mediated process. Importantly, 1.05 equiv of Weinreb amides are sufficient to obtain aryl enones in good yields.
LanguageEnglish
Pages2250-2253
Number of pages4
JournalOrganic Letters
Volume14
Issue number9
DOIs
Publication statusPublished - 17 Apr 2012

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Styrenes
Lithium
Amides
reagents
Temperature
styrenes
amides
lithium
temperature

Keywords

  • Bismesitylmagnesium
  • Shapiro reaction
  • electrophiles

Cite this

Kerr, William ; Morrison, Angus J ; Pazicky, Marek ; Weber, Tina. / Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent. In: Organic Letters. 2012 ; Vol. 14, No. 9. pp. 2250-2253.
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Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent. / Kerr, William; Morrison, Angus J; Pazicky, Marek; Weber, Tina.

In: Organic Letters, Vol. 14, No. 9, 17.04.2012, p. 2250-2253.

Research output: Contribution to journalArticle

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AU - Morrison, Angus J

AU - Pazicky, Marek

AU - Weber, Tina

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N2 - Bismesitylmagnesium has been shown to successfully mediate the Shapiro reaction. A range of tosylhydrazones has been subjected to the developed system, which furnishes exceptionally high incorporation of the introduced electrophiles and good yields of the functionalised styrenes. At conveniently accessible temperatures and with a comparably small excess of base reagent, this protocol offers an efficient alternative to the lithium-mediated process. Importantly, 1.05 equiv of Weinreb amides are sufficient to obtain aryl enones in good yields.

AB - Bismesitylmagnesium has been shown to successfully mediate the Shapiro reaction. A range of tosylhydrazones has been subjected to the developed system, which furnishes exceptionally high incorporation of the introduced electrophiles and good yields of the functionalised styrenes. At conveniently accessible temperatures and with a comparably small excess of base reagent, this protocol offers an efficient alternative to the lithium-mediated process. Importantly, 1.05 equiv of Weinreb amides are sufficient to obtain aryl enones in good yields.

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KW - Shapiro reaction

KW - electrophiles

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