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SingaCycle(TM)-E1 — Catalyst for the Heck-Mizoroki Reaction
No.144(March 2011)
A highly active, versatile and practical catalyst 1 for the Heck-Miozoroki Reaction has been developed by Ying et al. The palladium complex 1 consists of a sterically demanding N-heterocyclic carbene spectator ligand and a palladacycle as disposable part, releasing in situ the catalytically highly active mono-ligated Pd(0) species. Compound 1 is a robust and stable, ready to use catalyst which can be conveniently handled under air. 1 is available from discovery- to production scale amounts.
Typical procedure: 1a)
Aryl Bromide (1 mmol), olefin (1.2 mmol), K2CO3 (2.0 mmol) and 2 mol% NMP solution of SingaCycleTM-E1 (400 μL) are added to a vial with a magnetic stir bar. The atmosphere above the reaction mixture is purged with Ar over 30 sec. The vial is closed with a screw cap, and heated at 140 ºC with vigorous stirring over 18 h. After cooling, the reaction mixtures are filtered under dilution with CH2Cl2 (total: 20 mL). The crude product is loaded directly over a short pad of silica gel and purified by flash chromatography.
Aryl Bromide (1 mmol), olefin (1.2 mmol), K2CO3 (2.0 mmol) and 2 mol% NMP solution of SingaCycleTM-E1 (400 μL) are added to a vial with a magnetic stir bar. The atmosphere above the reaction mixture is purged with Ar over 30 sec. The vial is closed with a screw cap, and heated at 140 ºC with vigorous stirring over 18 h. After cooling, the reaction mixtures are filtered under dilution with CH2Cl2 (total: 20 mL). The crude product is loaded directly over a short pad of silica gel and purified by flash chromatography.
References
- 1)An NHC-ligated palladacycle as an active catalyst for the Heck-Mizoroki reaction
- a)E. A. B. Kantchev, G.-R. Peh, C. Zhang, J. Y. Ying, Org. Lett. 2008, 10, 3949.
- b)G.-R. Peh, E. A. B. Kantchev, C. Zhang, J. Y. Ying, Org. Biomol. Chem. 2009, 7, 2110.
- c)J. Y. Ying, E. A. B. Kantchev, PCT Int Appl. WO 08 156451, 2008.
- d)E. A. B. Kantchev, J. Y. Ying, Organometallics 2009, 28, 289.
- a)E. A. B. Kantchev, G.-R. Peh, C. Zhang, J. Y. Ying, Org. Lett. 2008, 10, 3949.
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