Amberlyst-15 in ionic liquid: An efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes

Ziyauddin S. Qureshi; Krishna M. Deshmukh; Pawan J. Tambade; Kishor P. Dhake; Bhalchandra M. Bhanage

doi:10.1002/ejoc.201000456

Amberlyst-15 in ionic liquid: An efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes

Ziyauddin S. Qureshi
, Krishna M. Deshmukh
, Pawan J. Tambade
, Kishor P. Dhake
, Bhalchandra M. Bhanage

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

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. A facile protocol involving Amberlyst-15 in the ionic liquid [Bmim][BF₄] (= 1-butyl-3-methylimidazolium tetrafluoroborate) has been developed for nucleophilic substitution of alcohols and hydroamination of alkenes.

Original language	English
Pages (from-to)	6233-6238
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.201000456
State	Published - Nov 2010
Externally published	Yes

Keywords

Amidation
Heterogeneous catalysis
Hydroamination
Ionic liquids
Nucleophilic substitution

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201000456

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@article{ef52eea0c36341a693726e7eadd9678e,

title = "Amberlyst-15 in ionic liquid: An efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes",

abstract = "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. A facile protocol involving Amberlyst-15 in the ionic liquid [Bmim][BF4] (= 1-butyl-3-methylimidazolium tetrafluoroborate) has been developed for nucleophilic substitution of alcohols and hydroamination of alkenes.",

keywords = "Amidation, Heterogeneous catalysis, Hydroamination, Ionic liquids, Nucleophilic substitution",

author = "Qureshi, \{Ziyauddin S.\} and Deshmukh, \{Krishna M.\} and Tambade, \{Pawan J.\} and Dhake, \{Kishor P.\} and Bhanage, \{Bhalchandra M.\}",

year = "2010",

month = nov,

doi = "10.1002/ejoc.201000456",

language = "English",

pages = "6233--6238",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "32",

}

TY - JOUR

T1 - Amberlyst-15 in ionic liquid

T2 - An efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes

AU - Qureshi, Ziyauddin S.

AU - Deshmukh, Krishna M.

AU - Tambade, Pawan J.

AU - Dhake, Kishor P.

AU - Bhanage, Bhalchandra M.

PY - 2010/11

Y1 - 2010/11

N2 - 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. A facile protocol involving Amberlyst-15 in the ionic liquid [Bmim][BF4] (= 1-butyl-3-methylimidazolium tetrafluoroborate) has been developed for nucleophilic substitution of alcohols and hydroamination of alkenes.

AB - 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. A facile protocol involving Amberlyst-15 in the ionic liquid [Bmim][BF4] (= 1-butyl-3-methylimidazolium tetrafluoroborate) has been developed for nucleophilic substitution of alcohols and hydroamination of alkenes.

KW - Amidation

KW - Heterogeneous catalysis

KW - Hydroamination

KW - Ionic liquids

KW - Nucleophilic substitution

UR - https://www.scopus.com/pages/publications/78249278127

U2 - 10.1002/ejoc.201000456

DO - 10.1002/ejoc.201000456

M3 - Article

AN - SCOPUS:78249278127

SN - 1434-193X

SP - 6233

EP - 6238

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

ER -

Amberlyst-15 in ionic liquid: An efficient and recyclable reagent for nucleophilic substitution of alcohols and hydroamination of alkenes

Abstract

Keywords

ASJC Scopus subject areas

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