SOLID-PHASE SYNTHESIS OF BIARYLS VIA THE STILLE REACTION

被引：87

作者：

FORMAN, FW ^{[1
]}

SUCHOLEIKI, I ^{[1
]}

机构：

[1] ELI LILLY & CO,SPHINX PHARMACEUT,CAMBRIDGE,MA 02139

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 03期

关键词：

D O I：

10.1021/jo00108a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 3-15% 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 21-33% 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 ual amide, carboxylic acid, or alcohol appendages.

引用

页码：523 / 528

页数：6

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