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CHELATION-CONTROLLE...
CHELATION-CONTROLLED, PALLADIUM-CATALYZED ARYLATION OF VINYL ETHERS
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LARHED, M (författare)
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ANDERSSON, CM (författare)
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HALLBERG, A (författare)
- UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,BOX 574,S-75123 UPPSALA,SWEDEN. ASTRA DRACO AB,DEPT MED CHEM,S-22100 LUND,SWEDEN. Danish Chemical Society, 1993
- 1993
- Engelska.
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Ingår i: Acta Chemica Scandinavica. - UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,BOX 574,S-75123 UPPSALA,SWEDEN. ASTRA DRACO AB,DEPT MED CHEM,S-22100 LUND,SWEDEN. : Danish Chemical Society. - 0904-213X .- 1902-3103. ; 47:2, s. 212-217
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http://actachemscand...
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https://urn.kb.se/re...
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https://doi.org/10.3...
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Abstract
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- 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.
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