Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent

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

Research output: Contribution to journal › Article

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

Fingerprint

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.
@article{fd6abd347278478aa3b6fe44d0f00da4,
title = "Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent",
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.",
keywords = "Bismesitylmagnesium, Shapiro reaction, electrophiles",
author = "William Kerr and Morrison, {Angus J} and Marek Pazicky and Tina Weber",
year = "2012",
month = "4",
day = "17",
doi = "10.1021/ol300652k",
language = "English",
volume = "14",
pages = "2250--2253",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "9",

}

Kerr, W, Morrison, AJ, Pazicky, M & Weber, T 2012, 'Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent' Organic Letters, vol. 14, no. 9, pp. 2250-2253. https://doi.org/10.1021/ol300652k

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 journal › Article

TY - JOUR

T1 - Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent

AU - Kerr, William

AU - Morrison, Angus J

AU - Pazicky, Marek

AU - Weber, Tina

PY - 2012/4/17

Y1 - 2012/4/17

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.

KW - Bismesitylmagnesium

KW - Shapiro reaction

KW - electrophiles

UR - http://pubs.acs.org/loi/orlef7

U2 - 10.1021/ol300652k

DO - 10.1021/ol300652k

M3 - Article

VL - 14

SP - 2250

EP - 2253

JO - Organic Letters

T2 - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -

Kerr W, Morrison AJ, Pazicky M, Weber T. Modified Shapiro reactions with bismesitylmagnesium as an efficient base reagent. Organic Letters. 2012 Apr 17;14(9):2250-2253. https://doi.org/10.1021/ol300652k

Access to Document