Sulfurated borohydride exchange resin: A novel reagent for selective reduction of aldehydes

Article abstract of DOI:10.1081/SCC-100105677

Selective reduction of aldehydes is carried out by using sulfurated borohydride exchange resin as a novel reducing reagent. Other sensitive groups like F, Cl, Br, NO₂, CN, OMe, ester and methylenedioxy remain intact under these reaction conditions. The isolation of pure products by simple filtration and evaporation is an important feature of this method.

Full text of DOI:10.1081/SCC-100105677

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SULFURATED BOROHYDRIDE EXCHANGE RESIN: A
NOVEL REAGENT FOR SELECTIVE REDUCTION OF
ALDEHYDES
a
a
B. P. Bandgar & V. T. Kamble
a
School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Organic
Chemistry Research Lab., Vishnupuri, Nanded, Maharashtra, 431 606, India
Published online: 16 Aug 2006.
To cite this article: B. P. Bandgar & V. T. Kamble (2001): SULFURATED BOROHYDRIDE EXCHANGE RESIN: A NOVEL REAGENT
FOR SELECTIVE REDUCTION OF ALDEHYDES, Synthetic Communications: An International Journal for Rapid Communication
of Synthetic Organic Chemistry, 31:19, 3037-3040
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SYNTHETIC COMMUNICATIONS, 31(19), 3037–3040 (2001)
SULFURATED BOROHYDRIDE
EXCHANGE RESIN: A NOVEL
REAGENT FOR SELECTIVE
REDUCTION OF ALDEHYDES
B. P. Bandgar* and V. T. Kamble
Organic Chemistry Research Lab.,
School of Chemical Sciences,
Swami Ramanand Teerth Marathwada University,
Vishnupuri, Nanded 431 606, Maharashtra, India
ABSTRACT
Selective reduction of aldehydes is carried out by using sulfu-
rated borohydride exchange resin as a novel reducing reagent.
Other sensitive groups like F, Cl, Br, NO , CN, OMe, ester
2
and methylenedioxy remain intact under these reaction con-
ditions. The isolation of pure products by simple filtration and
evaporation is an important feature of this method.
The high chemoselectivity, recovery and reusability of polymer sup-
1
2
ported reagents over non-supported reagents have prompted us to employ
sulfurated borohydride exchange resin (SBER) as a novel and selective
reducing reagent for aldehydes (Scheme).
*
Corresponding author. Fax: 0091-2462-29245; E-mail: upekam@hotmail.com
037
3
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

ORDER
REPRINTS
3
038
BANDGAR AND KAMBLE
Scheme.
A series of substituted aldehydes were subjected to SBER in methanol
ꢀ
at 25 C to get corresponding alcohols. The results are presented in table. It
is important to note that SBER chemoselectively reduces aldehyde group in
the presence of other sensitive functional groups like F (entry1), Cl (entry 2),
Br (entry 3), NO (entry 4), CN (entry 5), methoxy (entries 7–9), ester
2
(
entries 9, 10) and methylenedioxy (entry 11). Futhermore, aliphatic, aro-
matic and heterocyclic aldehydes are reduced to correponding alcohols
under these mild reaction conditions. It is worth commenting that aldehyde
group was selectively reduced in the presence of ketone group (entry 15).
Thus tolerance of different reducible groups to these reaction conditions
depicts the flexibility and generality of the protocol.
In conclusion, the present results demonstrate the novelty of SBER
which shows unique selectivity and constitutes a useful alternative to the
commonly accepted reduction procedures. Moreover, the superiority and
flexibility of the protocol lies in the ease of isolation of products by
simple filtration of the reagent that can be reactivated and reused without
appreciable loss of activity.
EXPERIMENTAL
All solvents were distilled before use. All chemicals were of analytical
grade.
General procedure for reduction of aldehydes with SBER: Sulfur
powder (2 mmol) and borohydride exchange resin (prepared using reported
1
c
method, 2 g) was added in methanol (10 mL) and stirred until colour of
resin becomes red (15–20 min), ensuring that BER changed to sulfurated
borohydride exchange resin (SBER). Then aldehyde (2 mmol) was added to
ꢀ
SBER and stirred at 25 C for specified time (table). A spontaneous reaction
took place which was observed by change in colour of the resin from red to
faint yellow. After completion of reaction (TLC) the resin was removed by
filtration and washed with methanol (2 Â 5 mL) and the combined filtrate
was concentrated under reduced pressure to yield alcohols.

ORDER
REPRINTS
SULFURATED BOROHYDRIDE EXCHANGE RESIN
3039
Table. Rapid and Selective Reduction of Aldehydes Using SBER

ORDER
REPRINTS
3
040
BANDGAR AND KAMBLE
REFERENCES
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Yoon, N.M. J. Org. Chem. 1995, 60, 3266. (e) Yoo, S.U.; Lee, S. Synlett
1990, 419. (f ) Sim, T.B.; Choi, J.; Yoon, N.M. Tetrahedron Lett. 1996,
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Received in the Netherlands October 12, 2000

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