CHELATION-CONTROLLED, PALLADIUM-CATALYZED ARYLATION OF VINYL ETHERS
1993 (English)In: Acta Chemica Scandinavica, ISSN 0904-213X, E-ISSN 1902-3103, Vol. 47, no 2, 212-217 p.Article in journal (Refereed) PublishedText
Chelation-controlled, palladium-catalyzed arylation of vinyl ethers with nitrogen-containing directing groups has been studied. Ethenyloxyalkylamines 1a-c and pyridines 2a-d, representing different carbon tethers were reacted with iodobenzene 4a and 1-iodonaphthalene 4b under phase-transfer conditions. The regioselectivity achieved is compared with the outcome from reactions with sterically similar vinyl ethers 3a-d. Arylations of the dimethylamine derivative 1a and the pyridine derivative 2a occurred at the terminal position of the olefins and were highly regioselective. A catalytic cycle for the regioselective, chelation-controlled vinylic substitution, involving a six-membered chelate ring, is proposed.
Place, publisher, year, edition, pages
UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,BOX 574,S-75123 UPPSALA,SWEDEN. ASTRA DRACO AB,DEPT MED CHEM,S-22100 LUND,SWEDEN., 1993. Vol. 47, no 2, 212-217 p.
IdentifiersURN: urn:nbn:se:uu:diva-275400DOI: 10.3891/acta.chem.scand.47-0212ISI: A1993KL28800016OAI: oai:DiVA.org:uu-275400DiVA: diva2:900236