catalyst

1. InCl3 CATALYZED ONE-POT
ORGANIC SYNTHESIS
Presented by:-
ABDUL MOTALEB
AMU,ALIGARH
EN No: GD4872

2. CONTENTS
 INTRODUCTION
 PREPARATION AND PROPERTIES OF InCl3
 ADVANTAGES OF InCl3
 MULTICOMPONENT REACTIONS
 InCl3 PROMOTED ORGANIC SYENTHESIS
 APPLICATIONS
 CONCLUSION
 REFERENCES

3. INTRODUCTION
 Presentation aims to illustrate the progress in a large
variety of InCl3 catalyzed reactions performed in
solvent and solvent free conditions.
 Synthetic potential of InCl3 mediated reactions,
which have recently emerged as useful strategy in
organic synthesis.
 A variety of two component and multicomponent
reactions catalyzed by InCl3 that led to the
production of structurally diverse compounds under
mild reaction conditions.

4. CONT…
 Study of the InCl3 catalyzed chemistry have been
the object of an interest which include the
development of new synthetic strategies, the
optimization of reaction conditions and the
application to the synthesis of bioactive
derivatives.
Ref: Yadav, J. S.; Aneesh, A.; Jimil, G.; Reddy, B. V. S. Eur. J. Org. Chem. 2010, 591.

5. PREPARATION AND PROPERTIES OF
InCl3
 InCl3 is prepared by the reaction of indium with
chlorine by gentle warming.
 2In +3Cl2 2InCl3
 InCl3 is a white, odorless, and highly deliquescent
powder.
 Its particles are flake or plate-shaped and highly
soluble in water and mineral acids.

6. ADVANTAGES OF InCl3
 Development of practical catalysts for efficient synthesis
is of key importance to both academia and the chemical
industry.
 Lewis acid catalysis has attracted much attention in
organic synthesis. These Lewis acids generally must be
used under strictly anhydrous conditions. The most
active Lewis acids such as BF3, TiCl4 and AlCl3 react
violently with water and can not be used under aqueous
conditions.
 In addition, recovery and reuse of the conventional
Lewis acids are also formidable tasks. These
disadvantages have restricted the use of Lewis acids in
organic synthesis under aqueous media.

7. CONT…
Some advantages are as follows
 Compatibility both to aqueous and organic solvent
 Water stability And Recyclability
 Highly chemo, regio and stereoselective.
 Operational simplicity
 A strong tolerance to oxygen and nitrogen containing
substrates and functional groups.
 Its lower heterophilicity makes it an ideal catalyst for
the C-C bond formation reactions.
 Harmless and environment friendly.
 InCl3 is not only compatible with water but also
cheaper than other indium salts.
Ref: Braga, A. L.; Schneider, P. H.;Paixao, M. W.; Deobald, A. M. Tetrahedron Lett.
2006, 47, 7195;

8. MULTICOMPONENT REACTIONS
 Multicomponent reactions (MCRs) has emerged as a
powerful tool in synthetic chemistry for the rapid
generation of molecular complexity and diversity.
 Among the various methods of bond formation and
bond cleavages, multicomponent reactions
undoubtedly occupy a prime position in organic
synthesis -
 Primarily due to their convergent nature.
 Superior atom-economy.
 Straightforward experimental procedure.
Ref: Adib, M.; Sheikhi, E.; Kavoosi, A.; Bijanzadeh, H. R. Tetrahedron 2010, 66, 9263.

9. InCl3 PROMOTED ORGANIC
SYENTHESIS
 Coupling of Aldehydes, Alkynes and Amines
 Synthesis of 1,3,5-tri-substituted benzenes
 Synthesis of 1,8-naphthyridines
 Synthesis of carbonyl compounds
 Synthesis of dihydropyranochromenediones
 Synthesis of coumarin derivatives
 InCl3-catalyzed Diels-Alder reaction, Friedel-crafts
reaction, Mannich reaction
 One-pot synthesis of quinolines
 Michael addition reaction
 Synthesis of functionalized benzof chromenes

10. COUPLING OF ALDEHYDES,
ALKYNES AND AMINES
Ref: Zhang, Y.; Li, P.; Wang, M.; Wang, L. J. Org. Chem. 2009, 74, 4364.

11. SYNTHESIS OF 1,3,5-TRI-SUBSTITUTED
BENZENES
InCl3
Ref: Xu, Y.-L.; Pan, Y.-M.; Wu, Q.; Wang, H.-S.; Liu, P.-Z. J. Org. Chem. 2011, 76, 8472.

12. InCl3-CATALYZED FRIEDEL-CRAFTS
REACTION
+
Ref: Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291;

13. SYNTHESIS OF
DIHYDROPYRANOCHROMENEDIONES
+
Ref: Reddy, B. V. S.; Reddy, M. R.; Narasimhulu, G.; Yadav, J. S. Tetrahedron Lett. 2010, 51, 5677.

14. ONE-POT SYNTHESIS OF
QUINOLINES
AROMATIZATION
Ref: Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813;

15. MUKAIYAMA-MICHEAL TYPE
REACTION
Ref: Chua, S.-S.; Alni, A.; Chan, L.-T. J.; Yamane, M.; Loh, T.-P. Tetrahedron 2011, 67,
5079.

16. SYNTHESIS OF COUMARINS
DERIVATIVES
Ref: Verma, R. K.; Verma, G. K.; Shukla, G.; Singh, M. S. RSC Adv. 2012, 2, 2413.

17. CONCLUSIONS
 The result summarized in this presentation clearly indicate
that there has been continues to be substantial interest in the
organic transformation promoted by indium chloride.
 InCl3 is being routinely used todays preparation in simple to
complex molecules and we described the importance of
indium chloride in the construction and functionalization of
various important scaffolds.
 Indium chloride is cheap, nontoxic, stable to water and
moisture and easy to handle, all these protocol represents an
optimal development with regard to economic and ecological
consideration.
 Major challenge in future would be to explore the utility of
InCl3 catalyzed protocol for the synthesis of hitherto
inaccessible and highly complex scaffolds.

18. REFERENCES
 Maya Shankar Singh, Keshav Raghuvanshi
TETRAHEDRON Report number 987.
Department of Chemistry (Centre of advanced Study), Faculty of Science, Banaras Hindu
University, Varanasi 221005, India.
Received on 31 may 2012