Nonmetal-catalyzed iodination of arenes with iodide and hydrogen peroxide

被引：107

作者：

Iskra, J

Stavber, S

Zupan, M

机构：

[1] Univ Ljubljana, Jozef Stefan Inst, Organ & Bioorgan Chem Lab, Ljubljana, Slovenia

[2] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana, Slovenia

来源：

SYNTHESIS-STUTTGART | 2004年 / 11期

关键词：

iodination; haloperoxidation; hydrogen peroxide; oxidative halogenation; aromatics;

D O I：

10.1055/s-2004-829136

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative iodination of arenes was carried out with one equivalent of KI and two equivalents of 30% hydrogen peroxide in MeOH in the presence of strong acid. Reactions of various substituted anisoles, phenols and anilines, as well as mesitylene and uracil, were selective and effective with very good yields of isolated halogenated aromatic molecules.

引用

收藏

页码：1869 / 1873

页数：5

相关论文

共 46 条

[1] A new, environment friendly protocol for iodination of electron-rich aromatic compounds [J].

Adimurthy, S ;

Ramachandraiah, G ;

Ghosh, PK ;

Bedekar, AV .

TETRAHEDRON LETTERS, 2003, 44 (27) :5099-5101

[2]

Alexander VM, 2003, SYNLETT, P1895

[3]

[Anonymous], 2000, PEROXIDE CHEM MECH P

[4] CERIUM(IV)-MEDIATED HALOGENATION AT C-5 OF URACIL DERIVATIVES [J].

ASAKURA, J ;

ROBINS, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4928-4933

[5] Simple and practical halogenation of arenes, alkenes and alkynes with hydrohalic acid/H2O2 (or TBHP) [J].

Barhate, NB ;

Gajare, AS ;

Wakharkar, RD ;

Bedekar, AV .

TETRAHEDRON, 1999, 55 (36) :11127-11142

[6] Electrophilic aromatic chlorination and haloperoxidation of chloride catalyzed by polyfluorinated alcohols: A new manifestation of template catalysis [J].

Ben-Daniel, R ;

de Visser, SP ;

Shaik, S ;

Neumann, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12116-12117

[7] The synthesis of 3',5'-diiodothyronine [J].

Block, P ;

Powell, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1070-1074

[8] Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2:: An environmentally favorable synthetic protocol [J].

Bora, U ;

Bose, G ;

Chaudhuri, MK ;

Dhar, SS ;

Gopinath, R ;

Khan, AT ;

Patel, BK .

ORGANIC LETTERS, 2000, 2 (03) :247-249

[9] Peroxometal-mediated environmentally favorable route to brominating agents and protocols for bromination of organics [J].

Bora, U ;

Chaudhuri, MK ;

Dey, D ;

Dhar, SS .

PURE AND APPLIED CHEMISTRY, 2001, 73 (01) :93-102

[10] An efficient, catalytic, aerobic, oxidative iodination of arenes using the H5PV2Mo10O40 polyoxometalate as catalyst [J].

Branytska, OV ;

Neumann, R .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9510-9512

← 1 2 3 4 5 →