Nobel Prize in Chemistry
2010
Mary P. Watson
Assistant Professor
Department of Chemistry & Biochemistry
October 29, 2010
The 2010 Nobel Laureates
Richard F. Heck
Photo: University of Delaware, USA
University of Delaware
Ei-ichi Negishi
Photo: Purdue University, USA
Purdue University
Akira Suzuki
Photo: Hokkaido University, Japan
Hokkaido University
Willis F. Harrington Professor
Emeritus
“for palladium-catalyzed cross couplings in organic synthesis”
Periodic Table
Image adapted from 0178120181524.deviantart.com
Forms of Palladium
www.americanelements.com!
www.coleparmer.com!
Bringing Carbons Together
+
C
C
C
C
C
C
C
C
C
C
Br
N
C
C
C
C
C
C
Br
C
C
C
C
C
C
C
Br
+
C
C
C
C
X
C
C
C
C
C
C
C
N
Heck’s Discovery: Palladium Brings Carbons Together
C
C
C
C
C
C
I
+
C
C
Pd
C
C
C
C
The Heck Reaction
1968, 1972
C
C
C
C
The Heck Reaction
C
C
C
C
C
C
+
I
C
C
C
Pd
C
C
C
Pd
C
C
C
C
I
C
C
C
Pd
C
I
Pd
C
C
C
C
C
C
C
C
C
C
C
C
Revolutionary Impact
“Heck Reaction” cited 118,998 times
The Heck Reaction changed the way molecules are made
and changed what molecules can be made.
Revolutionary Impact
O
C
O
C
C
C
C
O
C
Cl
N
C
C
C
S
C
C
C
C
SingulairTM
asthma treatment
C
CH3
naproxen
anti-inflammatory
O2
S
O
N
H
N
N
H
CF3
CO2H
OH
H3C
CH3
N
N
OMe
ProsulfuronTM
herbicide
n
PPV
OLED’s
www.coupondad.net
soilcrop.tamu.edu
www.pharmacyescrow.com
dgfvbd.110mb.com
octyl methoxycinnamate
sunscreen component
C
C
C
O
C
C
C
C
C
C
O
C
C
C
C
C
O
C
C
C
C
Revolutionary Impact
OMe
O
OH
H H Me
N
N
H H Me
N
N
MeN
H
morphine
opiate analgesic
N
N
H H Me
N
N
H H Me
quadrigemine C
antibacterial, analgesic
www.paradoxplace.com
www.resourcing.uk.com
farm4.static.flickr.com
The Negishi Reaction
1977
C
C
C
C
C
C
I
+
Zn
C
C
C
C
C
C
C
C
C
C
C
C
C
Pd
Pd
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
The Suzuki Reaction
1979
C
C
C
C
C
C
C
I
+
B
C
C
C
C
C
C
C
Pd
C
C
C
C
C
C
C
C
Important Applications
Dopant for liquid crystal displays
NC
F
F
C7H15
OC8H17
CH3
H3C
R
S
S
n
R
R
R
PPV
OLED
poly(thiophenes)
conducting polymers,
solar cells
img.diytrade.com
hubpages.com
www.oled-display.net
en.wikipedia.org/wiki/Polythiophene
n
Important Applications
Losartan Potassium
high blood pressure treatment
CH3
Cl
N
HO
N
N N
KN
N
OH
O
HO
O
H
HO2C
O
Cl
O
O
H
H
N
N
N
C
H
H H H
H
O2
NH
H2NOC
HO
Cl
H
N
OH
O
NHMe
N
H
O H C
3
CH3
OH
OH
Vancomycin derivative
potential antibiotic for MRSA
www.edrugsearch.com
en.wikipedia.org/wiki/Vancomycin-resistant_Staphylococcus_aureus
Heck’s Other Discoveries
C
C
C
C
C
C
I
+
C
Pd
C
C
C
C
C
C
C
Enabled Human Genome Project
(Sonogashira Coupling)
Mechanism of Hydroformylation
C
H
C
O
C
Used to produce 15 billion lbs/year
of alcohols and aldehydes
www.pbs.org/wgbh/nova/sciencenow/
www.reproductive-revolution.com
38643.tradenote.net
brandperfumes.wordpress.com
C
C
Heck’s Legacy
C
C
C
C
C
C
C
C
C
C
Heck’s
Fundamental
Insights
C
C
F
C
C–F Coupling
N
C
Buchwald–Hartwig
Coupling (C–N)
C
C
C
C
C
Stille Coupling
Hiyama Coupling
Kumada Coupling
Sonogashira Coupling
C
C
C
C
C
O
C
C–O Coupling
UD’s Heck Award and Lectureship
“To recognize visionary leadership in the field of organometallic
chemistry and to honor the contributions of Richard F. Heck”
S. Buchwald, MIT
R. Grubbs, CalTech
R. Bergman, Berkeley
2005
C–N Couplings
(Pd Catalysis)
2006
Olefin Metathesis
2007
C–H Activation
L. Overman, Irvine
B. Trost, Stanford
J. Hartwig, Illinois
2008
Intramolecular
Heck Reactions
(Pd Catalysis)
2009
Tsuji–Trost Reaction
(Pd Catalysis)
2010
C–N Couplings
(Pd Catalysis)
http://www.udel.edu/chem/organic/heck_award/index.html
Heck’s Chemical Path to Prominence
Human Health
& Medicine
Chemistry
Energy
Environment