1. Novel methods for iodination of heterocycles
Christopher Bilham
Santa Barbara City College, Chemical Engineering
Introduction
Cross-coupling reactions are powerful methods for
forming new carbon – carbon bonds which allows for
the synthesis of complex molecules. This is analogous
to a welder connecting two pieces of metal to make
useful parts and components. In order for these
reactions to be successful there must be a good leaving
group, usually iodine. However, current methods for
adding iodine onto a class of compounds known as
heterocycles have many problems associated with them.
We have set out to develop novel ways to perform
regioselective iodination using milder more
environmentally friendly reaction conditions. The
ability to perform high yielding iodination of a wide
variety of heterocycles in mild conditions is imperative
to exploiting their use in pharmaceuticals,
agrochemicals and materials.
Methods
Results Conclusions
Acknowledgements
 Small scale reactions were set up under
anhydrous conditions
• Continuously Stirred
• Started at lowest possible temperature reagents
were soluble
 Monitored by Thin Layer Chromatography
(TLC)
• Temperature was raised accordingly with TLC
results
• Determines length of reaction
 Isolated through Column Chromatography or
Recrystallization
 Characterized by Proton Nuclear Magnetic
Resonance (H-NMR)
The Zakarian Group
-Dr. Armen Zakarian
-Lindsay Smith
-Aaron Herrmann
INSET
- Dr. Jens-Uwe Kuhn
- Dr. Maria Napoli
- Dr. Nick Arnold
- Assisting Faculty
Mentor: Lindsay Smith Faculty Advisor: Armen Zakarian
 N-Methylpyrrole is successfully iodinated with
a high yield of our desired mono-iodinated
product by using TriFluroacetic Acid (TFA) as
an activator, N-IodoSuccinimide (NIS) as our
iodine source in TetraHydroFuran (THF) our
solvent. Both of our goals of high yield and
regioselectivity were achieved.
 Dibenzofuran is successfully iodinated with a
good yield of desired mono-iodinated product
using both: NIS in TFA and NIS in HexaFluro-
2-Propanol (HFIP). Although not as
successful as N-Methylpyyrole these
conditions will likely be optimized for 100%
conversion.
 Our data indicates that direct iodination of
heterocycles under mild conditions can be
achieved with regiocontrol and high yield.
Further work is required to determine the
scope of substrates these conditions are
successful on, but a strong precedent for
success has been illustrated by our data.