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CHELATION-CONTROLLED, PALLADIUM-CATALYZED ARYLATION OF ENOL ETHERS WITH ARYL TRIFLATES - LIGAND CONTROL OF SELECTION FOR ALPHA-ARYLATION OR BETA-ARYLATION OF [2-(DIMETHYLAMINO)ETHOXY]ETHENE
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
1994 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 50, no 2, 285-304 p.Article in journal (Refereed) Published
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Abstract [en]

Palladium-catalyzed arylation reactions of [2-(Dimethylamino)ethoxy]ethene (1) with a series of aryl triflates were performed under a variety of reaction conditions. In particular, the influence of phosphine ligands and halide additives on regioselectivity were studied. It was found that the chelation-controlled arylation of 1 affords an expedient route for the conversion of phenols into arylacetaldehydes. Alternatively, the same starting materials could be used to synthesize acetophenones by reversing the regioselectivity with bidentate phosphine ligands.

Place, publisher, year, edition, pages
UPPSALA UNIV, UPPSALA BIOMED CTR, DEPT ORGAN PHARMACEUT CHEM, S-75123 UPPSALA, SWEDEN. ASTRA DRACO AB, PRECLIN RES & DEV, DEPT MED CHEM, S-22100 LUND, SWEDEN., 1994. Vol. 50, no 2, 285-304 p.
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URN: urn:nbn:se:uu:diva-275399DOI: 10.1016/S0040-4020(01)80755-9ISI: A1994MR16000001OAI: oai:DiVA.org:uu-275399DiVA: diva2:900234
Available from: 2016-02-03 Created: 2016-02-03 Last updated: 2017-11-30

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