Regioselective iodination of arenes in ionic liquids mediated by the Selectfluor™ reagent F-TEDA-BF4

被引：36

作者：

Chiappe, C ^{[1
]}

Pieraccini, D ^{[1
]}

机构：

[1] Dipartimento Chim Bioorgan & Biofarm, Via Bonanno 33, I-56126 Pisa, Italy

来源：

ARKIVOC | 2002年

关键词：

aromatic iodination; iodoarenes; ionic liquids;

D O I：

10.3998/ark.5550190.0003.b22

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of aromatic compounds was regioselectively iodinated with iodine and F-TEDA in imidazolium- and pyridinium-based ionic liquids, [bmim][PF6] and [bpyr][BF4]. Iodination was para- directed when possible, otherwise it occurred in the ortho- position. The substrate selectivity measured in competitive experiments is in agreement with a polar mechanism.

引用

页码：249 / 255

页数：7

共 25 条

[1] AROMATIC IODINATION WITH THE I-2-HGX(2) COMBINATION [J].

BACHKI, A ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON, 1994, 50 (17) :5139-5146

[2] MECHANISM OF ELECTROPHILIC AROMATIC SUBSTITUTIONS - COMMENTS ON A RECENT CRITICISM CONCERNING THE USE OF THE MESITYLENE/DURENE REACTIVITY RATIO AS A PROBE TO DISTINGUISH BETWEEN IONIC AND ET PATHWAYS [J].

BACIOCCHI, E ;

GALLI, C .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1995, 8 (08) :563-565

[3] A simple preparation of iodoarenes, iodoalkenes and iodoalkynes by reaction of organolithiums with 2,2,2-trifluoro-1-iodoethane [J].

Blackmore, IJ ;

Boa, AN ;

Murray, EJ ;

Dennis, M ;

Woodward, S .

TETRAHEDRON LETTERS, 1999, 40 (36) :6671-6672

[4] NEWER ASPECTS OF ELECTRON-TRANSFER IN ELECTROPHILIC AROMATIC NITRATION - RADICAL PAIRS AS REACTIVE INTERMEDIATES BY TIME-RESOLVED SPECTROSCOPY [J].

BOCKMAN, TM ;

KOCHI, JK .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1994, 7 (07) :325-351

[5]

BRADZIL LC, 1996, J ORG CHEM, V61, P9621

[6]

Dietrich F, 1998, METAL CATALYZED CROS

[7] Ionic liquids. Green solvents for the future [J].

Earle, MJ ;

Seddon, KR .

PURE AND APPLIED CHEMISTRY, 2000, 72 (07) :1391-1398

[8] AN EFFICIENT AND SELECTIVE METHOD FOR THE PREPARATION OF IODOPHENOLS [J].

EDGAR, KJ ;

FALLING, SN .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5287-5291

[9]

FABBRINI M, 2001, J CHEM SOC P2, P1526

[10] 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

← 1 2 3 →