Palladium-catalyzed cross coupling of Grignard reagents with in situ-derived enol phosphates

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 7111-7114

  Miller, Joseph A ^a  

^a DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; PHOSPHATE; REAGENT;

ARTICLE; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; GAS CHROMATOGRAPHY; METHODOLOGY; REACTION TIME; STOICHIOMETRY;

EID: 0037163310     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01600-3     Document Type: Article

References (11)

1. For Ni-catalyzed cross coupling of an enol triflate with an aryl Grignard reagent, see: Busacca C.A., Eriksson M.C., Fiaschi R. Tetrahedron Lett. 40:1999;3101.
2. For a review of enol triflate chemistry, including Ni- and Pd-catalyzed cross coupling reactions, see: Ritter K. Synthesis. 1993;735.
3. nMn: Fugami, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 2203.
4. nMn: Fugami, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 2203.
5. nMn: Fugami, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 2203.
6. nMn: Fugami, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 2203.
7. nMn: Fugami, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 2203.
8. nMn: Fugami, K.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 2203.
9. These results were obtained by GC analysis of a reaction sample (containing tridecane as an internal standard) quenched in a mixture of 1 M sodium citrate (aq.) and ether.
10. Stuermann M., Weidenbruch M., Klinkhammer K.W., Lissner F., Marsmann H. Organometallics. 17:1998;4425.
11. 4), concentrated, and then distilled using a Kugelrohr apparatus (oven temp.=120-150°C; 0.1 torr) to provide 3.51 g of 1-phenyl-3,4-dihydronaphthalene (85% yield based on 1-tetralone).