Biographical Sketches
Yuanmin Zhang was born in Gansu, P. R. of China and received
her B.Sc. degree (2009) in Chemistry from Tianshui Normal University.
She is currently pursuing her M.Sc. degree under the supervision of
associate professor Dr. Zhengyin Du at the College of Chemistry and
Chemical Engineering, Northwest Normal University. Her research
interests focus on the development of new synthetic methodologies
for green chemistry.
Introduction
Introduction
<P>Samarium triiodide (SmI3) is a yellow powder with
a melting point of 820 ˚C, unstable towards air
and moisture. It is commercially available and has been widely used
in organic reactions, such as elimination, conjugate addition, carbonyl
reduction, intramolecular cyclization and nucleophilic substitution
reactions. It can also be regarded as an efficient metal catalyst
and a Lewis acid catalyst to accelerate reactions and to improve
yields for organic transformations. Herein, the applications of
SmI3 in recent years are listed and reviewed.</P>
Abstracts
Abstracts
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(A) A novel and highly
efficient method for the conjugate addition of indoles with electron-deficient
olefins catalyzed by SmI3 afforded a series of new 3-substituted
indole derivatives.
[¹]
[²]
This reaction is highly
regioselective and can be accelerated by microwave irradiation with
silica gel as catalyst support.
[³]
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</TD>
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(B) The Michael reaction
of β-diketones with α,β-unsaturated esters catalyzed
by samarium triiodide was achieved in THF under reflux to give the
corresponding δ-carbonyl esters in good yields.
[4]
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</TD>
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(C) The nucleophilic
substitution reaction between N-(1-benzotriazol-1-ylalkyl)amides
and 1,3-dicarbonyl compounds promoted by samarium triiodide was
reported. This provides a useful method for the preparation of Mannich-type
products with good yields and high diastereoselectivities.
[5]
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</TD>
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(D) Catalyzed by SmI3,
a series of arylamines reacted with dihydropyran to give pyrano[3,2-c]quinoline derivatives in moderate
to good yields with high trans diastereoselectivity.
[6]
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</TD>
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(E) A simple methodology
to prepare (E)-α-hydroxy-β,γ-unsaturated
amides from α,β-epoxyamides, by using catalytic
samarium triiodide, has been developed. This elimination reaction
proceeds with total or high diastereoselectity and regioselectivity.
[7]
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</TD>
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(F) 1,1-Diacetates undergo
deprotection and condensation reaction with cycloalkanones in the
presence of catalytic samarium triiodide to afford α,α′-bis(substituted
benzylidene)cycloalkanones in good yields.
[8]
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</TD>
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(G) A new and facile
method to prepare (Z)-allylic iodides 2 from the acetates of Baylis-Hillman
adducts 1 mediated by samarium triiodide
was developed in ionic liquid [bmim]BF4 with
excellent yields and good stereoselectivity.
[9]
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</TD>
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(H) A novel, one-pot
three-component reaction of aldehydes, α-halo ketones and
(phenylsulfonyl)acetonitrile was achieved in good yields in the
presence of samarium triiodide.
[¹0]
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</TD>
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(I) SmI3-promoted β-elimination
reactions of α-chloro-β-hydroxy ketones offer
a highly efficient way to synthesize α,β-unsaturated ketones
in good yields and E-diastereoselectivity.
[¹¹]
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</TD>
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(J) Samarium triiodide can also be
used for the catalytic reduction of the saturated steroidal ketone
into the corresponding secondary alcohol.
[¹²]
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</TD>