Abstract
Language | English |
---|---|
Pages | 2250-2253 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 14 |
Issue number | 9 |
DOIs | |
Publication status | Published - 17 Apr 2012 |
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Keywords
- Bismesitylmagnesium
- Shapiro reaction
- electrophiles
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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 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 -