An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst

被引：77

作者：

Das, Biswanath ^{[1
]}

Venkateswarlu, Katta ^{[1
]}

Krishnaiah, Maddeboina ^{[1
]}

Holla, Harish ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 49期

关键词：

aromatic and heteroaromatic compounds; nuclear bromination; NBS; sulfonic-acid-functionalized silica; regioselectivity; heterogeneous recyclable catalyst;

D O I：

10.1016/j.tetlet.2006.10.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, efficient and rapid method has been developed for high-yielding regioselective nuclear monobromination of aromatic and heteroaromatic compounds using NBS in the presence of sulfonic-acid-functionalized silica at room temperature. The catalyst works under heterogeneous conditions and can be recycled. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8693 / 8697

页数：5

共 25 条

[1] A NEW MILD AND SELECTIVE REAGENT FOR NUCLEAR BROMINATION [J].

BISARYA, SC ;

RAO, R .

SYNTHETIC COMMUNICATIONS, 1993, 23 (06) :779-788

[2] Selective halogenation of flavanones [J].

Bovicelli, P ;

Bernini, R ;

Antonioletti, R ;

Mincione, E .

TETRAHEDRON LETTERS, 2002, 43 (32) :5563-5567

[3] MARINE HALOPEROXIDASES [J].

BUTLER, A ;

WALKER, JV .

CHEMICAL REVIEWS, 1993, 93 (05) :1937-1944

[4] HOST GUEST COMPLEXATION .32. SPHERANDS COMPOSED OF CYCLIC UREA AND ANISYL UNITS [J].

CRAM, DJ ;

DICKER, IB ;

LAUER, M ;

KNOBLER, CB ;

TRUEBLOOD, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7150-7167

[5] Regioselective ring-opening of aziridines with potassium thiocyanate and thiols using sulfated zirconia as a heterogeneous recyclable catalyst [J].

Das, B ;

Ramu, R ;

Ravikanth, B ;

Reddy, KR .

TETRAHEDRON LETTERS, 2006, 47 (05) :779-782

[6] Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines [J].

Das, B ;

Thirupathi, P ;

Mahender, I ;

Reddy, VS ;

Rao, YK .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 247 (1-2) :233-239

[7] An efficient one-pot synthesis of polyhydroquinolines at room temperature using HY-Zeolite [J].

Das, Biswanath ;

Ravikanth, Bommena ;

Ramu, Ravirala ;

Rao, Bommena Vittal .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (07) :1044-1045

[8] A simple, efficient and highly selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using silica supported sodium hydrogen sulfate as a heterogeneous catalyst [J].

Das, Biswanath ;

Reddy, K. Ravinder ;

Thirupathi, P. .

TETRAHEDRON LETTERS, 2006, 47 (33) :5855-5857

[9]

De la Mare P. B., 1997, ELECTROPHILIC HALOGE

[10]

Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222

← 1 2 3 →