SIMPLE AND EFFICIENT SYSTEM FOR THE α-BROMINATION OF A β-KETOESTER BY USING N-BROMOSUCCINIMIDE IN THE PRESENCE OF SILICA-SUPPORTED NaHCO3 AS THE HETEROGENEOUS CATALYST: AN ENVIRONMENTALLY BENEVOLENT APPROACH

被引：12

作者：

Rahman, Ateeq ^{[1
]}

Jonnalagadda, S. B. ^{[1
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem, ZA-4000 Durban, South Africa

来源：

SYNTHETIC COMMUNICATIONS | 2012年 / 42卷 / 08期

关键词：

Acyclic ketones; alpha-bromination; beta-ketoesters; NaHCO3-SiO2; catalyst; NBS (N-bromosuccinimide); INFRARED-ABSORPTION SPECTRA; X-RAY-DIFFRACTION; ATOM-TRANSFER; ENANTIOSELECTIVE FLUORINATION; RADICAL CYCLIZATION; SELECTIVE REDUCTION; GLASSES; KETONES; ACID; MANGANESE(III);

D O I：

10.1080/00397911.2010.530729

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective and efficient alpha-bromination of beta-ketoesters and cyclic and acyclic ketones is achieved by reaction with N-bromosuccinimide (NBS) catalyzed by silica-supported sodium bicarbonate (NaHCO3 center dot SiO2) under mild reaction conditions and with short reaction times. With 100% selectivity with all substrates, after 45 min at room temperature (20 +/- 2 degrees C), conversions for ethylacetoacetate were 67% and for acetophenone, cyclohexanone, and cycloheptanone were 58, 50, and 55%, respectively. Acetyl acetone recorded 65% conversion with 100% selectivity. Although cyclopentanone and toluene had only 20% conversion, both reactions showed 100% selectivity toward alpha-bromination. The catalysts exhibit activity and reusability.

引用

页码：1091 / 1100

页数：10

共 10 条

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TETRAHEDRON LETTERS, 2005, 46 (17) : 3041 - 3044
[2] Regioselective -Bromination of Aralkyl Ketones Using N-Bromosuccinimide in the Presence of Montmorillonite K-10 Clay: A Simple and Efficient Method
Mohan, Reddy Bodireddy
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SYNTHETIC COMMUNICATIONS, 2013, 43 (19) : 2603 - 2614
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Shaterian, Hamid Reza
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PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) : 3127 - 3135
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Ramesh, C
Ravindranath, N
Das, B
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18): : 7101 - 7103
[6] Silica-supported barium chloride (SiO2-BaCl2) - Efficient and heterogeneous catalyst for the environmentally friendly preparation of N, N ′-alkylidene bisamides under solvent-free conditions
Mohammad Shafiee M.R.
Canadian Journal of Chemistry, 2011, 89 (05) : 555 - 561
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Shafiee, Mohammad Reza Mohammad
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Das, Biswanath
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TETRAHEDRON LETTERS, 2011, 52 (27) : 3521 - 3522
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Chaskar, Atul
Padalkar, Vikas
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GREEN CHEMISTRY LETTERS AND REVIEWS, 2013, 6 (03) : 217 - 221
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Ahuja, Monika
Reen, Gagandeep Kour
Kumar, Ashok
Sharma, Pratibha
CHEMISTRY LETTERS, 2016, 45 (07) : 752 - 754

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