1. RSI-C 2013
IIT MADRAS
PROJECT PRESENTATION
ORGANIC SYNTHESIS
-
V.SUCHARITA
Under the guidance of
Prof S.Sankararaman,
Dept. of chemistry, IITM

2. MOTIVATION!!
 Inclination
towards chemistry.
 Suzuki coupling – 2010 Nobel winning
reaction.
 Unique catalyst used & reaction
being completed in the shortest time
known.
 The 2nd product being synthesized for
the FIRST TIME in literature!!

3. ORGANIC SYNTHESIS
SUZUKI COUPLING REACTIONS
– AN INTRO
 A coupling reaction in organic chemistry is a catch-all term
for a variety of reactions where two hydrocarbon fragments
are coupled with the aid of a metal catalyst.
 The Suzuki reaction is an organic reaction of an arylor vinyl-boronic acid with an aryl- or vinyl-halide catalyzed by
a palladium(0) complex.
It is widely used to synthesize poly-olefins, styrenes, and
substituted biphenyls, and has been extended to incorporate
alkyl bromides.
R1 BY2
+
R2 X
Pd catalyst
Base
R1 R2

4. OBJECTIVE OF OUR PROJECT
The main aim of our project was to synthesize :
*1,3,6,8-tetraphenyl
pyrene
*1,3,6,8-tetrakis(4-paraethoxy)
phenylpyrene

5. STRUCTURES TO BE FAMILIAR WITH :
1. PYRENE :
4. 1,3,6,8-TETRABROMOPYRENE :
Br
Br
2. BENZOPHENONE :
O
Br
3. 1,4-DIOXAN :
O
O
Br
HO
5. PHENYLBORONIC ACID :
OH
B

6. SUZUKI COUPLING –
REACTION MECHANISM

Preparation of Pd(0) catalyst –
L2Pd(II)Cl
L2Pd(0)
Active catalyst
 Suzuki coupling : Mechanism –
2
+
NaOH
+
HO
L2Pd(0)
+
Ar Ar
+
HO
B
OH
Na Br

7. CATALYST
Trans-bis(1,4-dimesityl-3methyl-1,2,3-triazol 5ylidene)
palladium(ll)dichloride:

8. PREPARATION OF
1,3,6,8-TETRAPHENLYPYRENE:
CHEMICALS USED:
1,3,6,8 – tetrabromopyrene (C16H6Br4)
 Phenylboronic acid (C6H7BO2)
 Palladium (ll) catalyst (PdCl2MTz )
 Triphenylphosphene (PPh3 )
 Sodium hydroxide (NaOH)
 1,4 – dioxan (C4H8O2)
TABLE1.xls


9. PREPARATION OF
1,3,6,8-TETRAPHENLYPYRENE:

10. PREPARATION OF
1,3,6,8-TETRAKIS(4-ETHOXYPHENYL)PYRENE :







CHEMICALS REQUIRED:
1,3,6,8 – tetrabromopyrene (C16H6Br4)
Para-ethoxyphenylboronic acid (C8H11BO3)
Palladium (ll) catalyst (PdCl2MTz )
Triphenylphosphene (PPh3 )
Sodium hydroxide (NaOH)
1,4 – dioxan (C4H8O2 )
table-2.xlsx

11. PREPARATION OF
1,3,6,8-TETRAKIS(4-ETHOXYPHENYL)PYRENE :

12. CRYSTALLIZATION :



Crystallization is a natural/artificial
process of formation of solid crystals
precipitating from a solution.
We should select solvents such that
the product is sparingly soluble in
the solvent and the impurities are
completely soluble.
For 1,3,6,8-tetraphenylpyrene we
used a mixture of 1,2-dichloroethane,
dichloromethane and cyclohexane.

13. CRYSTALLIZATION :

The 2nd product
1,3,6,8-tetrakis(4ethoxyphenyl)pyrene
was crystallized using
1,2-dichloroethane
and cyclohexane as
the solvents.

14. THIN LAYER CHROMATOGRAPHY :



Thin layer chromatography is a technique used to separate
mixtures.
TLC can be used to monitor and observe the progress of a
reaction, determine the purity of the product and identify
the various compounds present.
TLC sheet is made of glass, plastic or aluminium and is
coated on one side with silica gel.
HOW IT IS DONE :

15. ACTION UNDER UV AND FLUROSCENCE

UV :

FLUROSCENCE :

16. NUCLEAR MAGNETIC RESONANCE
[NMR] :



Nuclear magnetic
resonance (NMR) is a physical
phenomenon in which nuclei in
a magnetic field absorb and reemit electromagnetic radiation.
This energy is at a
specific resonance frequency
which depends on the strength of
the magnetic field and the
magnetic properties of
the isotope of the atoms.
NMR allows the observation of
specific quantum mechanical
magnetic properties of the atomic
nucleus.

17. NUCLEAR MAGNETIC RESONANCE
[NMR] WORKING :
•
•
•
Sample dissolved in suitable solvent (deuteriated) is
put in a very strong magnetic field.
Atomic nuclei with a nuclear spin has different
energy levels.
Nuclear spin = l ==> Different energy} (2l+1)
levels available }

18. Sample
irradiated with
radiofrequency
Emitted
energy is
recorded with
a radio
receiver.
Energy given
out as nuclei
comes back to
low energy
level.
NMR
CYCLE
Disrupts the
equilibrium b/w
energy levels.
Nuclei absorbs
energy.
Promoted to
higher level.

23. PLAYING AROUND WITH
FLUROSCENCE !

26. SUMMARY
 Suzuki coupling reaction.
 Synthesis of 2 compounds.
 Crystallization.
 Thin layer chromatography.
 Nuclear magnetic resonance
 Fluorescence emitted by crystals.

27. ACKNOWLEDGEMENT
Prof. S. Sankararaman;
Dept of chemistry, IIT-M
 Mr. Mohan;
Dept. of chemistry, IIT-M
 Mr. Jeelani Basha and Mr.
Sureshbabu; PhD students
working under Prof.
Sankararaman.
 RSI-C 2013 and all the organizing
institutions.
 Our peers and our parents.

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