Novel 2,2-bipyridine ligand for palladium-catalyzed regioselective carbonylation

Organic Letters

Volumn 1, Issue 5, 1999, Pages 745-747

  Wu, George Guangzhong ^a   Wong, YeeShing ^a   Poirier, Marc ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000305384     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990123s     Document Type: Article

References (15)

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2. (a) Wakefield, B. J. Organolithium Methods; Academic Press: New York, 1988; p 86.
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9. (c) After we finished our experiments, two related papers published: Chambers, R. J.; Marfat, A. Synth. Commun. 1997, 515. Najiba, D.; Carpentier, J.-F.; Castanet, Y.; Biot, C.; Brocard, J.; Mortreux, A. Tetrahedron Lett. 1999, 40, 3719.
10. (c) After we finished our experiments, two related papers published: Chambers, R. J.; Marfat, A. Synth. Commun. 1997, 515. Najiba, D.; Carpentier, J.-F.; Castanet, Y.; Biot, C.; Brocard, J.; Mortreux, A. Tetrahedron Lett. 1999, 40, 3719.
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14. Recently, chrial derivatives of 2,2-bipyridine were used as chiral ligands for palladium reactions: Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1998, 9, 531.
15. 2, 5.0 g (32 mmol) of 2,2-bipyridine, 2.5 L of toluene, 127 mL (1.1 mol) of aniline, and 194 mL (1.4 mol) of DBU. The autoclave was sealed, evacuated, purged with nitrogen, and charged with CO to 80 psi. The mixture was heated to 65°C for about 40 h while keeping the pressure at 80 psi, cooled to 25°C, and filtered through a pad of Celite with aid of water. The layers were separated, and the organic layer was concentrated. Crystallization of the residue from 2-PrOH gave the desired amide in 76-82% isolated yield.The purity of the isolated product was >98% and the solution yield was 90% as determined by HPLC.