Amberlyst-15 in Ionic Liquid: An Efficient and Recyclable Reagent for Nucleophilic Substitution of Alcohols and Hydroamination of Alkenes

被引：40

作者：

Qureshi, Ziyauddin S. ^{[1
]}

Deshmukh, Krishna M. ^{[1
]}

Tambade, Pawan J. ^{[1
]}

Dhake, Kishor P. ^{[1
]}

Bhanage, Bhalchandra M. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 32期

关键词：

Hydroamination; Heterogeneous catalysis; Ionic liquids; Nucleophilic substitution; Amidation; CATALYZED INTERMOLECULAR HYDROAMINATION; BENZYL ALCOHOLS; ALLYLIC ALCOHOLS; DIRECT AMINATION; SULFONAMIDES; AMIDATION; ALKYLATION; COMPLEXES; KETONES;

D O I：

10.1002/ejoc.201000456

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nucleophilic substitution reaction of secondary alcohols and hydroamination of alkenes with amides, sulfonamides, carbamates, and amines using Amberlyst-15 immobilized in [Bmim][BF4] (1-butyl-3-methylimidazolium tetrafluoroborate) ionic liquid as an efficient recyclable reagent is described. The solvent effect is prominent in the reaction, and the desired substitution products are obtained in good to excellent yield. The protocol is advantageous due to the ease of handling of the reagents, the simple work-up procedure, and the environmentally benign conditions that allow effective recyclability.

引用

页码：6233 / 6238

页数：6

共 36 条

[1] Amberlyst-15® in ionic liquid: an efficient and recyclable reagent for the benzylation and hydroalkylation of β-dicarbonyl compounds
Qureshi, Ziyauddin S.
Deshmukh, Krishna M.
Tambade, Pawan J.
Bhanage, Bhalchandra M.
TETRAHEDRON LETTERS, 2010, 51 (04) : 724 - 729
[2] Amberlyst-15®:: a novel and recyclable reagent for the synthesis of 1,5-benzodiazepines in ionic liquids
Yadav, JS
Reddy, BVS
Eshwaraiah, B
Anuradha, K
GREEN CHEMISTRY, 2002, 4 (06) : 592 - 594
[3] Synthesis of Substituted Aryl Ketones by Addition of Alcohols to Alkynes Using Amberlyst-15/Ionic Liquid as a Recyclable Catalytic System
Wagh, Kishor V.
Bhanage, Bhalchandra M.
SYNLETT, 2015, 26 (06) : 759 - 764
[4] Formylation and acetylation of alcohols using Amberlyst-15® as a recyclable heterogeneous catalyst
Singh, Abhilash S.
Bhanage, Bhalchandra M.
Nagarkar, Jayashree M.
GREEN CHEMISTRY LETTERS AND REVIEWS, 2012, 5 (01) : 27 - 32
[5] MILD AND EFFICIENT ALLYLATION OF INDOLES AND AMIDES USING AMBERLYST-15 AS A RECYCLABLE HETEROGENEOUS CATALYST
Liu, Zhe
Wang, Dong
Wu, Yanchao
Chen, Yongjun
SYNTHETIC COMMUNICATIONS, 2012, 42 (12) : 1813 - 1823
[6] Direct α-Alkylation of Acetophenones with Benzhydrols as Well as 1-Phenylethanols Using Amberlyst-15/Ionic Liquid as an Efficient Catalytic System
Wagh, Kishor V.
Bhanage, Bhalchandra M.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (02): : 445 - 450
[7] An Efficient One-Pot Synthesis of Spiro [indole-pyrazolobenzothiazepine] Derivatives in Ionic Liquid Using Amberlyst-15 As a Reusable Catalyst
Dandia, Anshu
Gupta, Shyam L.
Jain, Anuj K.
CURRENT GREEN CHEMISTRY, 2014, 1 (01) : 80 - 85
[8] Synthesis of several types of 2,8-dioxabicyclo[3.3.1]nonanes using amberlyst-15 as an efficient recyclable heterogeneous catalyst
Samanta, Swati
Sepay, Nayim
Mallik, Sumitava
Mondal, Rina
Molla, Mosidur Rahaman
Mallik, Asok K.
SYNTHETIC COMMUNICATIONS, 2017, 47 (23) : 2195 - 2201
[9] Amberlyst-15©: An efficient heterogeneous reusable catalyst for selective anti-Markovnikov addition of thiols to alkenes/alkynes and for thiolysis of epoxides
Lanke, Satish R.
Bhanage, Bhalchandra M.
CATALYSIS COMMUNICATIONS, 2013, 41 : 29 - 33
[10] Direct nucleophilic substitution reaction of alcohols mediated by a zinc-based ionic liquid
Zhu, Anlian
Li, Lingjun
Wang, Jianji
Zhuo, Kelei
GREEN CHEMISTRY, 2011, 13 (05) : 1244 - 1250

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