RESEARCH ARTICLE
Microwave‐assisted facile synthesis of propargylamine
library by robust nitro functionalized cross‐linked
polystyrene resin supported Cu NPs
Anuj S. Sharma | Harjinder Kaur | Nirav Barot
Department of Chemistry, School of
Sciences, Gujarat University, Ahmedabad,
India
Correspondence
Harjinder Kaur, Department of Chemistry,
School of Sciences, Gujarat University,
Ahmedabad, India.
Email: hk_ss_in@yahoo.com
Funding information
GUJCOST, Grant/Award Number: /MRP/
2014‐15/403
Abstract
In the present investigation, we study catalytic activity of copper nanoparticles
stabilized onto a nitro functionalized polystyrene resin (Cu NPs@ Nitro‐Resin).
The size of stabilized copper nanoparticles was found between 3 and 9 nm. This
work reports a cost‐effective and sustainable protocol for the synthesis of
propargylamines. Herein, we have developed microwave‐assisted synthesis of
propargylamine from 3 components coupling of aldehyde, alkynes, and amines
(A
3
coupling) in truly heterogeneous catalytic system. Reaction parameters,
such as solvent, catalyst concentration reaction time, and recyclability, were
investigated, and reaction conditions were optimized. The present method
has advantages such as environmentally benign, ease to handle, short reaction
time (≈25 min), excellent yields (98%), low E‐factor (0.15), and high atom
economy (94%).
KEYWORDS
A
3
coupling, microwave heating, nanocatalysis, propargylamines, resin supported nanoparticles
1 | INTRODUCTION
In the 21st century, there has been an increased awareness
towards green chemistry approach to synthesize of
important organic moieties. The need for developing sus-
tainable reaction protocols with state‐of‐the‐art use of
technology, alternate reaction media, energy saving,
waste minimization, etc has become vital. One such tech-
nique that has gained attention is synergistic use of
microwave reactors and nanoparticles as catalyst. In the
last few decades, microwave radiation in synthetic
organic chemistry became popular and attracted consid-
erable practical and theoretical attention along with the
development of resource friendly and environmentally
benign processes in terms of sustainable chemistry.
[1,2]
Although use of homogeneous and heterogeneous cata-
lysts is common under microwave heating, there are
some important parameters that need to be looked
carefully. During the reaction process, there is not only
usual agglomeration and Ostwald ripening of nanoparti-
cles but also increased chances of sintering and hot spot
development even at low temperature as metal nanoparti-
cles are efficient absorbers of microwave. So careful choice
of solvents, supports, reaction temperature, etc needs to be
evaluated.
[3–6]
Transition metal catalyzed multicomponent reactions
are a powerful synthetic strategy to generate multiple
molecular scaffolds and to increase structural as well as
skeletal, diversity from simple and readily available mole-
cules.
[7]
Three components coupling of aldehyde, alkynes,
and amines (A
3
coupling) is one of the best examples of
such a process, and this transformation has received much
more attention in recent year. Propargylamine scaffolds
show remarkable biological activity and are used in drugs
such as rasagiline, a potent cardiovascular drug.
[8]
Besides,
they also act as enzyme inhibitors,
[9]
antitumor,
[10]
Received: 16 February 2017 Revised: 25 April 2017 Accepted: 30 June 2017
DOI: 10.1002/poc.3749
J Phys Org Chem. 2017;e3749.
https://doi.org/10.1002/poc.3749
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