Efficient and scalable arylation of bicyclic lactones to form quaternary centers using conventional and microwave radiation

Tetrahedron Letters

Volumn 46, Issue 40, 2005, Pages 6871-6873

  Malcolm, Scott C ^a   Ribe, Seth ^a   Wang, Fengjiang ^a   Hewitt, Michael C ^a   Bhongle, Nandkumar ^a   Bakale, Roger P ^a   Shao, Liming ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

Arylation; Microwave; Palladium; Quaternary center

Indexed keywords

AROMATIC COMPOUND; LACTONE;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE RADIATION; PROTEIN QUATERNARY STRUCTURE; RADIATION;

EID: 27744549856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.030     Document Type: Article

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12. 1 mmol scale. The lactone was weighed out into a flamedried vial. The catalyst was added and covered in anhydrous toluene before the flask was purged with nitrogen and sealed. The phosphine was then added as a solution in toluene and stirred for 2 min. To this was added LiHMDS and, finally, the aromatic bromide, leading to a slight exotherm and precipitation of the salt. After 16 h at 50 °C, the solution was diluted with hexanes and 10% aqueous HCl and stirred for 10 min. The organic layer was separated, dried, and evaporated. The residue was separated by silica gel chromatography to yield the aromatic lactone.
13. 3, δ, mult): 178.6 (0), 140.5 (0), 128.8 (1), 127.3 (1), 126.3 (1), 70.3 (2), 52.5 (0), 41.0 (1), 34.2 (2), 27.5 (2), 23.4 (2), 23.2 (2).
14. 3, δ, mult): 174.4 (0), 164.9 (0), 157.1 (0), 130.0 (1), 126.6 (1), 125.7 (0), 123.7 (0), 121.1 (1), 110.9 (1), 79.3 (1), 55.7 (3), 23.4 (2), 21.8 (2), 21.7 (2), 20.2 (2).
15. 4 and filtered. Finally, the solvent was removed in vacuo and the residual oil was separated on silica gel.