Journal of Organic Chemistry p. 523 - 528 (1995)
Update date:2022-08-11
Topics:
Forman, Frank W.
Sucholeiki, Irving
The solid-phase synthesis of biphenyls by heterogenous cross-coupling of trialkylphenylstannanes with aryl electrophiles is described.Tributylphenyltin attached by an amide bond to the Rink amide resin undergoes palladium-catalyzed coupling with aryl triflates and aryl iodides to produce after acid cleavage 4-biphenylacetamide in 3-15percent yield. 4-Iodophenylacetic acid attached to the Rink amide resin by an amide bond also undergoes heterogeneous palladium-catalyzed coupling with trialkylphenyltins to give after acid cleavage of the support 4-biphenylacetamide in 21-33percent yield. 4-Iodobenzylbromide was then attached to the photocleavable (+/-)-2-methoxy-5-<2-<(2-nitrophenyl)dithio>-1-oxopropyl>phenylacetamide (NpSSMpact) resin through the formation of a thioether bond.Both substituted and unsubstituted trimethylphenyltins were shown to undergo palladium-catalyzed Stille coupling with the resin bound aryl iodide to give after photolytic cleavage biphenyls containing no residual amide, carboxylic acid, or alcohol appendages.
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