Electrophilic aromatic thallation of phenol ethers: An improved experimental procedure

被引：6

作者：

dosSantos, ML

deMagalhaes, GC

Braz Filho, R

机构：

[1] UNIV BRASILIA, DEPT QUIM, BR-70910 BRASILIA, DF, BRAZIL

[2] UNIV ESTADUAL NORTE FLUMINENSE, LTA CCTA, SETOR QUIM PROD NAT, BR-28015650 SAO JOSE DOS CAMPOS, RJ, BRAZIL

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1996年 / 526卷 / 01期

关键词：

thallium; electrophilic thallation; electron-rich arenes; arene; aryl; phenol;

D O I：

10.1016/S0022-328X(96)06338-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

In this report we present a simple modification of the classical electrophilic aromatic thallation reaction, in which iodination of several phenol ethers can be achieved in high yields under very mild reaction conditions with the mixture TTFA/BF3 . Et(2)O/ClCH2CH2Cl, whereby both oxidative dimerizations and hydrolysis have been successfully suppressed.

引用

收藏

页码：15 / 19

页数：5

相关论文

共 17 条

[1] SYNTHESIS OF AN ISOSTEGANE FROM MATAIRESINOL [J].

CAMBIE, RC ;

DUNLOP, MG ;

RUTLEDGE, PS ;

WOODGATE, PD .

SYNTHETIC COMMUNICATIONS, 1980, 10 (11) :827-831

[2] ELECTROPHILIC AROMATIC-SUBSTITUTION - CHARGE-TRANSFER EXCITED-STATES AND THE NATURE OF THE ACTIVATED COMPLEX [J].

FUKUZUMI, S ;

KOCHI, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (24) :7240-7252

[3] OXIDATIVE ARYL-BENZYL COUPLING - BIOMIMETIC ENTRY TO PODOPHYLLIN LIGNAN LACTONES [J].

KENDE, AS ;

LIEBESKIND, LS ;

MILLS, JE ;

RUTLEDGE, PS ;

CURRAN, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) :7082-7083

[4] BIARYL SYNTHESIS VIA COUPLING OF ARYLTHALLIUM BIS(TRIFLUOROACETATES) WITH A CATALYTIC AMOUNT OF LITHIUM TETRACHLOROPALLADATE [J].

KJONAAS, RA ;

SHUBERT, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (11) :1924-1925

[5] THALLIUM IN ORGANIC-SYNTHESIS .46. OXIDATIVE COUPLING OF AROMATIC-COMPOUNDS USING THALLIUM(III) TRIFLUOROACETATE - SYNTHESIS OF BIARYLS [J].

MCKILLOP, A ;

TURRELL, AG ;

TAYLOR, EC .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :764-765

[6]

MCKILLOP A, 1969, TETRAHEDRON LETT, P2427

[7] THALLIUM IN ORGANIC SYNTHESIS .22. ELECTROPHILIC AROMATIC THALLATION USING THALLIUM(III) TRIFLUOROACETATE - SIMPLE SYNTHESIS OF AROMATIC IODIDES [J].

MCKILLOP, A ;

HUNT, JD ;

ZELESKO, MJ ;

FOWLER, JS ;

TAYLOR, EC ;

MCGILLIVRAY, G ;

KIENZLE, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (19) :4841-+

[8] THALLIUM IN ORGANIC-SYNTHESIS .58. REGIOSPECIFIC INTERMOLECULAR OXIDATIVE DEHYDRODIMERIZATION OF AROMATIC-COMPOUNDS TO BIARYLS USING THALLIUM(III) TRIFLUOROACETATE [J].

MCKILLOP, A ;

TURRELL, AG ;

YOUNG, DW ;

TAYLOR, EC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6504-6512

[9]

MCKILLOP A, 1969, TETRAHEDRON LETT, P2423

[10]

Taylor E. C., 1970, J AM CHEM SOC, V92, P2175