ELECTROSYNTHESIS OF UNSYMMETRICAL POLYARYLS BY A S(RN)1-TYPE REACTION

被引：19

作者：

BOY, P ^{[1
]}

COMBELLAS, C ^{[1
]}

SUBA, C ^{[1
]}

THIEBAULT, A ^{[1
]}

机构：

[1] ECOLE SUPER PHYS & CHIM IND VILLE PARIS,CHIM & ELECTROCHIM MAT MOLEC LAB,F-75231 PARIS,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unsymmetrical polyaryls are electrosynthesized in liquid ammonia by a single-step S(RN)1 reaction in the presence of a redox mediator starting from aromatic halides and 2,6-di-tert-butyl phenoxide. With monoaryl halides activated by electron-withdrawing substituents (N of pyridyl or quinolyl, trifluoromethyl, cyano, sulfone, ester, ketone, alkyl sulfide, N+ of anilinium), biaryls are obtained in good yields (between 50 and 95%). The yields of ter- and quateraryls are lower (40% maximum). The reaction is extended to other ortho-disubstituted phenols. Elimination reactions of the tert-butyl groups from the products are achieved by a Friedel-Crafts reaction using either trifluoromethanesulfonic acid or aluminum trichloride as catalysts.

引用

页码：4482 / 4489

页数：8

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