UPDATES
Handy Protocols using Vinyl Nosylates in Suzuki–Miyaura Cross-Coupling Reactions
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General Procedure E – in situ Nosylation of Cyclic
Diketones Followed by Suzuki Coupling (Table 4,
Conditions D)
To a solution of diketone (1 equiv.) in dry and degassed
THF (6 mLmmolÀ1) were added successively nitrobenzene-
sulfonyl chloride (1.1 equiv.) and potassium carbonate
(4 equiv.). After 20 min were added degassed water
(1.4 mLmmolÀ1), phenylboronic acid (1.2 equiv.) and
PdCl2(dppf) (4 mol%). The mixture was stirred at 308C
under an inert atmosphere until consumption of the starting
material. The reaction was quenched by addition of saturat-
ed NH4Cl. After extraction with ethyl acetate, the combined
organic layers were washed with water and brine, dried over
Na2SO4 and concentrated under reduced pressure. The
crude residue was purified by chromatography on silica gel
(cyclohexane/ethyl acetate).
Supporting Information
Experimental details and spectroscopic data of all com-
1
pounds, as well as copies of their H and 13C NMR spectra,
are available in the Supporting Information.
Acknowledgements
The authors thank the CNRS and the French Agency of Re-
search (ANR 09-BLAN-0329 CADISCOM) for financial
support. NPC also thanks the ANR for a PhD fellowship.
A.D. thanks the French Ministry of Research for a PhD fel-
lowship.
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