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Explore Synthetic Chemistry beyond Explore Synthetic Chemistry beyond Functional Group TransformationsFunctional Group TransformationsExplore Synthetic Chemistry beyond Explore Synthetic Chemistry beyond Functional Group TransformationsFunctional Group Transformations
13th Annual Green Chemistry and Engineering Conference, Washington DCJune 22-26, 2009
13th Annual Green Chemistry and Engineering Conference, Washington DCJune 22-26, 2009
C.C.--J. LiJ. LiDepartment of ChemistryDepartment of Chemistry
McGill UniversityMcGill University
C.C.--J. LiJ. LiDepartment of ChemistryDepartment of Chemistry
McGill UniversityMcGill University
Today, we are facing great challengesToday, we are facing great challengesToday, we are facing great challengesToday, we are facing great challenges
--economy crisiseconomy crisis--energy crisisenergy crisis--environmental crisisenvironmental crisis--resource crisisresource crisis
• >97% of all manufactured products involve one or more chemical processes
• of the resources removed from the Earth, only 10% are retained in the product and 90% are waste (Referred by Buzz Cue)
• how do we reconcile these facts with maintaining a healthy environment?
The Grand Challenge of Sustainability
1. Prevention rather than remediation2. Atom Economy3. Less Hazardous Chemical Syntheses4. Designing Safer Chemicals5. Safer Solvents and Auxiliaries6. Design for Energy Efficiency7. Use of Renewable Feedstocks 8. Reduce Derivatives 9. Catalysis10. Design for Degradation11. Real-time analysis for Pollution Prevention12. Inherently Safer Chemistry for Accident Prevention
Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice, Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice, Oxford University Press: New York, 1998Oxford University Press: New York, 1998
12 Principles of Green Chemistry
Synthesis in LabSynthesis in Lab
Starting materialca. 60 steps
Synthesis in NatureSynthesis in Nature
Starting materialone pot
catalysis/air/water
The Basis of Modern Organic SynthesesThe Basis of Modern Organic Syntheses
1) Protection–deprotection, protection-deprotection…(70-80%)
2) Halogenation-dehalogenation, halogenation- dehalogenation… (Grignard, substitution, radical, carbene)
3) Oxidation-reduction, oxidation-reduction….
Explore New Chemical ReactivitiesExplore New Chemical Reactivities
1. Grignard-type reactions in water
2. Reactions based on the reaction of C-H Bonds
3. C-C bond formation based on Cross C-H/C-H coupling
HOX
PX'/base/organic solvent
POX
MPO
MX
HOCHO
PX'/base/organic solvent
POCHO
PO OP
OH
Y-HO OH
OH
X,base,solventwaste/seperation
X,base,solventwaste/seperation
MX,orgnic solventwaste/seperation
P, Y,solventwaste/seperation
Grignard reaction in water
HOX
M
OHMX
HOCHO
MX,H2Owaste/seperation
HO OH
OH
Eliminate Reaction I. Eliminate Reaction I. Simplifying protectionSimplifying protection--deprotectionsdeprotections
SIALIC ACIDS SYNTHESIS: An ExampleSIALIC ACIDS SYNTHESIS: An ExampleSIALIC ACIDS SYNTHESIS: An ExampleSIALIC ACIDS SYNTHESIS: An Example
OHO
X
HO HO
CO2HHO
HOO
XHOHOHO OH
HO H
OH
OHOH
OH O
BrCO2H
HOOH
XOH
OH OH CO2HHO
OH
XOH
OH CO2HOH
OOHHO
HOHO OH
HO H
OH
OHOH
OH O
BrCO2Me HO
OH
OHOH
OH OH CO2MeHO
OH
OHOH
OH
In/H2O
CO2Me
+
OH
X=OHX=NHAc
OHO
HO
HO HO
CO2HHO
HO
mannose
Li & Chan, 1992
Chan, 1995
6:1
+
O3
HOOH
OHOH
OH OH
O
CO2Me
In/H2O+ +
KOH
(+) KDN
O3
6:1
RH
RX
X2
RMgX
MmOn
ROH(Tf)2O/Et3N
ROTf
NaX
RX
RMgX
Mg
Mg
R' R"O
R' R"
OH
R
R'X + RX2 +RX3 ...
solvent+drying agents
Mg(OH)X+solvent
MmOn-1+ isomers
NEt3HOTf+solvent
NaOTf + solvent
solvent+drying agents
Mg(OH)X+solvent
RH
R' R"
O
R' R"
OH
R
2. Eliminate More Reactions:2. Eliminate More Reactions:Minimizing halogenationMinimizing halogenation--dehalogenationdehalogenation
Possibly in water
R HO
MeOH
ROH O
MeMe
(3 mol%)+
H2O, 110 oC, 5h
RuCl2(PPh3)3
Wang, M.; Li, C. J. Tetrahedron Lett. 2002, 43, 358.
AldolAldol--type reaction via allylic Ctype reaction via allylic C--H H activation in wateractivation in water
Summary: catalytic addition of terminal alkyne to Summary: catalytic addition of terminal alkyne to various nucleophiles in watervarious nucleophiles in water
HR
R'
OH
R
N
R' H
"R CORN
R'
"R COR
R
H
N
R' H
"R R(H)N
R'
"R R(H)
RO
R' Cl
R'
O
R
R'
O
R'
O
R
R'
O
R
R'
O
cat. M
R'-H/[O]
R'R
H
H
N
R' H
"R
NH
R'
"R
R
N
R'
H Ts
RN
R' H
Ts
H2O
NR
PhPh
PhR1 N
CH2
CH2
R2
R2
O
R'''N O
R'R''
O
R
R'H
R1
O
OH
R3
R2
R'
OH
RF3C
O
R' CF3
RCHO
RNH2RCHOCO2
OR'
O
R H
OR'
O
Explore CExplore C--C Bond FormationC Bond Formation beyond Functional beyond Functional Group TransformationsGroup Transformations
H
H
Functional group
Functional group
A Simple DreamA Simple Dream
R2C
R1
R3
HR5
C
R4
R6H+
R2C
R1
R3R5
C
R4
R6
+ HOH1/2 O2
HOH
[cat]
no protection of any functional groups
What the “…..” (censored) are you talking about?
[cat] = [Fe], [Cu], or no catalyst at all
Cross-Dehydrogenative-Coupling (CDC) Reaction
A Hypothetical DesignA Hypothetical Design
C H C H
electron rich electron poor
high-oxidation stateM
low-oxidation stateM
• Where shall we start from?
Oxidation Activation of Oxidation Activation of αα--Amine CAmine C--H BondH Bond
A3 Coupling
R1N
CH2R3
R2
R1N
R2
R3
Mn
R1N
CH2
R2
R3
+SET -H
Mn+1
Leonard, N. J.; Leubner, G. W. J. Am. Chem. Soc. 1949, 71, 3408–3411
R1N
R2
R3
M
R1 H +R2 H
O+ R3R4NH
cat. MLn
R2
NR3R4
R1*
NCH
R1
R2
NCH
R1
R2
R3
R4
R4
J. Am. Chem. Soc. 2005, 127, 6968.
Eur. J. Org. Chem. 2005, 0000.
J. Am. Chem. Soc.2004, 126, 11810.
Org. Lett.2004, 6, 4997.
NHN
CH
R1
R2
R3 NH
J. Am. Chem. Soc. 2005, 127, 3672.
NCH
R1
R2
R3
NO2
R4
HNO2
R4
H
H
R3H
R4HN
CH
R1
R2
R3R4*
HEWG
EWGN
CH
R1
R2
R3
EWG
EWG
Cross-Dehydrogenative-Coupling (CDC) Reaction
NCH
R1
R2
R3
R4
H R6
R5
R4
R6
R5
Proc. Natl. Acad. Sci. 2006, 103, 8928-8933.
Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
CDC: sp3 C-H with sp C-H
+
CuBr (5 mol%)
100 oC, 3h
tBuOOH (1.0-1.2 eq)N Ph N
Ph
36 %
Selection of copper catalystSelection of copper catalystaa
+N
[Cu] (5 mol%)
100 oC, 3hN
entry catalyst NMR yieldb
1 CuBr 77
3
56
7
8
9
CuCl
CuI
75
56
CuOTf 25
Cu(OTf)2
Cu(I)2Se 61
8
no 0
a 4mmol aniline, 2 mmol phenylacetylene, 0.1 mmol copper salt, and 0.8 ml tBuOOH (5-6 M in decane)were used; b Reported yields were based on alkynes and determined by NMR using an internal standard.
2 CuB2 72 (NMR)
4 CuCl2 73
tBuOOH
H R+Ar N
CuBr (5 mol%)
100 oC, 3hAr N
R
74 %
tBuOOH (1.0-1.2 eq)
N
82 %
NOMe
74 %
NMe
74 %
NBr
36 %
N
N 40 %
N OH
58 %
N OO
Et
12 %
NBu
73 %
N
69 %
N
53 %
N
Me
Me Br
Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
0.5 ~ 5 mol% CuBr
room temperature R1 NR2
R3R1 N
R2
+EWG EWG
EWG
HR3
HEWG
1 eq 1 eq
t BuOOH1 eq
Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 3173.
CDC: sp3 C-H with sp3 C-H
yields [%]entry
1
3
4
5
6
7
8
9
10
74
72
65
82
78
70
71
70
56
58
product
N
COOMeMeOOC
N
COOEtEtOOC
Ph
Ph
N
COOiPri PrOOC
N
COOtBut BuOOC
Ph
Ph
N
COOCH2PhPhCH2OOC
N
COOMeMeOOC
Ph
Ph-o-OMe
N
COOEtEtOOC
N
COOMeMeOOC
Ph-o-OMe
Ph-p-OMe
N
COOEtEtOOC
Ph-p-OMe
2
yields [%]entry product
Li, Z.; Li, C.-J. Eur. J. Org. Chem. 2005, 3173.
N R1+
Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968.
CDC: sp3 C-H with sp2 C-H
5 mol% CuBr TBHP N R1
NH
RFG
NHFG
R
C&EN News, May 23, 2005
N Ph
NH
N Ph
NHMe
N PhNHMe
N Ph
NHO2N
N Ph
NH
NO2
N Ph
NHMeO
N
NHMeO OMe
N
NHOMe
entry product yield entry product yield
1
2
3
4
8
9
10
11
86 (79)
89 (57)
80 (61)
81 (77)
(85)
64 (50)
95 (71)
98 (65)
N
NHOMeO2N
N
OMeNHMe
12
13
78 (50)
95 (49)
N Ph
NHO
O5 77 (63)
N Ph
NHCl
N Ph
NMe
7
6
89 (73)
58 (44)
entry product yield
C&EN News, May 23, 2005
Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 3672.
CDC: sp3 C-H with sp3 C-H
R1 NR2
R3
+ ROH + H2OR4
NO25 mol% CuBr1.0 eq. TBHP
room temperatureR1 N
R2
+
R4
NO2H
R3
H
fuse
Basle, O.; Li, C.-J. Green Chemistry 2007, 9, 1047.
CDCCDC with Owith O22 in waterin water
N
R3
H
R2
R1
N
R3
R2
R1
R4
NO2
N
R3
R2
R1
CO2R5
CO2R5
R4
H NO2
CO2R5
H CO2R5
CuBr (cat.)
O2 (1 atm)H2O
H2O
H2O
NPh
NPh
NO2
cat.M
2 equiv MeNO2 O2 (1 atm)
60°C
entry solvent RuCl3(mol %)
CuBr(mol %)
12
3
4
56
H2OH2O
H2O
H2O
H2OH2O
510
5
5
50
0
1
2
5
0
5
NMR yieldb
4567
62
73
9090
1a 3a
Reaction time (h)
1818
18
18
1816
7 MeOH 0 5 9016
Table 1 Optimization of reaction conditionsa
a Tertiary amine (0.2 mmol) and nitroalkane (0.4 mmol) were stirred under O2 (1 atm)at 60°C in 0.6 mL of water. b NMR yields based on tetrahydoisoquinoline using an internal standard.
Basle, O.; Li, C.-J. Green Chemistry 2007, 9, 1047.
90%
90% 95%
75%30%
NPh
NO2
NPh
NO2
NPh
NO2
NMe
NO2
N
NO2
N
NO2 OMe
N
NO2 OMe
N
NO2 OMe
95%
80% 85%
NPh
OO
OMeMeO
NPh
OO
OEtEtO
82% 80%
Basle, O.; Li, C.-J. Green Chemistry 2007, 9, 1047.
N
R3
H
R2
R1
N
R3
R2
R1
R4
NO2
N
R3
R2
R1
CO2R5
CO2R5
R4
H NO2
CO2R5
H CO2R5
CuBr (cat.)
O2 (1 atm)H2O
H2O
H2O
Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
Asymmetric CDC: sp3 C-H with sp C-H
N R1N R1
R2
R2Cat.[Cu] / L*
t-BuOOH+
*
NO
N N
O
CDC with EthersCDC with Ethers
OO MeO OMe
O O
MeO OMe
O O
Zhang, Y.; Li, C.-J. Angew. Chem. Int. Ed., 2006, 45, 1949.
+O H
H
R3
R4R2
InCl3/Cu(OTf)2(5mol%/5mol%)
DDQCH2Cl2, RT
O
R2
R3
R4+ + DDQH2
R1R1
CDC without metal catalystCDC without metal catalyst
OR1
OR1
R3
R2
O
R3
O
R2+ DDQ
heat
Zhang, Y. Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242.
N R2
R1
R3
R4N R2
O
O
R1
R3
R4
O
O
R5
R5
R5
R5H
H+
r.t.
H2O
Zhang, H. B.; Liu, L.; Chen, Y. J.; Wang, D.; Li, C. -J. Eur. J. Org. Chem. 2006, 869-873
O
O
CN
CN
Cl
Cl+
O
O
CN
CNCl
Cl
OR1
OR1
HH
R3
OR2
HH
OR1
R3
R2
O
+
OH
OH
CN
CN
Cl
Cl
H Nu+ (2)H NuCDC reaction
TsujiTsuji--Trost Reaction via CDC CouplingTrost Reaction via CDC Coupling
Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56.
cat [Cu]
80 oC, over nightMe Me
O O+
Me Me
O O
cat [Co] TBHP
61%
LGPd
:NuNu
"Pd"(1)H
+R1
R2
O
R3
O
10 mol% FeCl2R1
H
R3 R2
O O
25-87%
tBuOOtBu 80 oC, 8h
Li, Z.; Cao, L.; Li, C.-J. Angew. Chem. Int. Ed. Engl. 2007, 46, 6505.
Simple AlkanesSimple Alkanes
Zhang, Y.; Li, C. J. Eur. J. Org. Chem. 2007, 4654-4657.
OEt
Ph
O
O
OEt
Ph
O
O
+20% FeCl2
tBuOOtBu (2.0)
79%80 0C
AreneArene--Alkylation by AlkanesAlkylation by Alkanes
Deng, G.; Zhao, L.; Li, C. J. Angew. Chem. Int. Ed. 2008, 47, 6278.
N +cat[Ru]
N[O]
80%
N+
CDC of Pyridinium Oxide with AlkanesCDC of Pyridinium Oxide with Alkanes
Deng, Yanagisawa, Itami, Li Chem. Eur. J. 2009, 0000
N+
O-
N+
O-N+
O-
2.2 : 181%
tBuOOtBu(1 equiv)
135 oC, 15 h+ +
CDC of Pyridine with AlkanesCDC of Pyridine with Alkanes
Deng, Li Org. Lett. 2009, 0000
NN
80%
tBuOOtBu(1 equiv)
135 oC, 15 h cat. Sc(OTf)3
+
SiteSite--Specific Peptide ModificationSpecific Peptide Modification
Some Applications:Some Applications:
NH
MeOHN
OOEt
O+
10 mol% CuBr1.0 equiv. TBHP
Ar, DCE, 70oC, 4 h 63% N
H
MeOHN
OOEt
O
Direct Functionalization of PeptideDirect Functionalization of Peptide
Direct Functionalization of Glycine Derivatives Direct Functionalization of Glycine Derivatives (rapid synthesis of (rapid synthesis of angiotensin converting enzyme inhibitorsangiotensin converting enzyme inhibitors )
Zhao, L.; Li, C. J. Angew Chem. Int. Ed. 2008, 47, 7075.
HN
O
NH
O
Pd/C, 50 psi H2
MeOH, RT
HN
O
NH
O
84%
TCCA, 2 equiv. HCl
H2O/ CH3CN, RT
-Cl+H3NNH
O
88%
10 mol% CuBr1.0 equiv. TBHP
Ar, CH2Cl2, RT12-16 h
HN
O
NH
O
+
68%
PMPHN
O
NH
OEt
O CuBr/TBHPPMP
HN
O
NH
R
Nu
+ Nu
[a] Reaction conditions: aryl boronic acid (0.20 mmol), peptide (0.30 mmol), TBHP (36 µL, 5-6 M in decane), CuBr (0.02 mmol), DCE (0.5 mL). [b] Isolated yields are based on aryl boronic acid, and NMR yields using an internalstandard are given in parentheses. [c] d.r. (diastereomer ratio) was determined by HPLC analysis. d.r. of the product is 3:5. [d] Reaction was performed using peptide as the limiting reagent at 70 oC, phenylactetylene was usedat 3.0 equiv..[e] Reactions were performed using peptide as the limiting reagent at room temperature, indole was used at 1.5 equiv..[f] Reaction was performed using dipeptide as the limiting reagent at room temperature in DCM, diethyl zinc was used at 2 equiv.
6 h 77 (83)
reaction time yield (%)b
11 h
11 h
12 h
12 h
73 (88)
76 (84)
61 (95)
74 (100)
3 h 94 (100)
12 h 57 (91) 4 h 63
PMPHN
NH
OOEt
OPh
PMPHN
NH
OOEt
OPMP
PMPHN
NH
OOEt
OPMP
PMPHN
NH
OOEt
O
PMPHN
NH
OOEt
O
PMPHN
NH
OOEt
OS
PMPHN
NH
OOEt
OO
PMPHN
NH
OOEt
O
product
Cl
10 h 71 (72)
PMPHN
NH
OOEt
O
R1
Table 3a α-Functionalization of dipeptides and tripeptides
PMPHN
O
NH
HN
OOEt
O
6 h 57 (100)
reaction time yield (%)b
11 h
24 h
36 h
54
47 (54)
57 (62)
10 h 59 (88)
12h 84 (100)
12 h 65PMPHN
NH
O HN
OOEt
O
Ph
PMPHN
NH
O HN
OOEt
O
PMP
PMPHN
NH
O HN
OOEt
O
PMPHN
NH
O HN
OOEt
O
S
PMPHN
NH
O HN
OOEt
O
O
PMPHN
NH
O HN
OOEt
O
Ph
PMPHN
NH
O HN
OOEt
O
Ph
1 h 52PMP
HN
NH
O HN
OOEt
O
12 h 89PMP
HN
NH
O HN
OOEt
O
NH
Ph
product
12 h 68 (71)
PMPHN
NH
O HN
OOEt
O
R2
1
entry
4
5
7
8
3
2c 9d
6
10e
11f
entry
13
15
16
17c
12
18c
19d
20e
14
or
Ph
12 h 73PMP
HN
NH
OOEt
O
NH
reaction time yield (%)bproductentry
12 h 61PMPHN
NH
OOEt
O
21
Zhao, Basle, Li, PNAS, 2009, 4106,.
Chemistry Beyond Functional Group TransformationsChemistry Beyond Functional Group Transformations
C-H + C-H C-CCross-Dehydrogenative-Coupling (CDC)
Acc. Chem. Res., 2009, 42, 335-344.Proc. Natl. Acad. Sci. (USA), 2009, 4106Org. Lett, 2009, 11, 1171.Chem. Eur. J.. 2009, 15, 333.Angew. Chem. Int. Ed. Engl. 2008, 47, 7075Angew. Chem. Int. Ed. Engl. 2008, 47, 62780Angew. Chem. Int. Ed. Engl. 2007, 46, 6505Eur. J. Org. Chem. 2007, 4654Green Chemistry 2007, 9, 1047Proc. Natl. Acad. Sci. (USA), 2006, 103, 8928J. Am. Chem. Soc. 2006, 128, 4242Pure & Appl. Chem. 2006, 78, 935Tetrahedron: Asymmetry, 2006, 17, 590Angew. Chem. Int. Ed. Engl. 2006, 45, 1949J. Am. Chem. Soc. 2006, 128, 56Adv. Cat. Syn. 2006, 348, 229Eur. J. Org. Chem. 2006, 869J. Am. Chem. Soc. 2005, 127, 6968J. Am. Chem. Soc. 2005, 127, 3672Eur. J. Org. Chem. 2005, 3173Org. Lett. 2004, 6, 4997J. Am. Chem. Soc. 2004, 126, 11810
“We shall escape the absurdity of growing a whole chickenin order to eat the breast or wing
[within the next 50 years] by growing these parts separately
under a suitable medium.”
---- Winston Churchill Fifty Years Hence (1930)
artisticportraits.com/ churchill.jpg
© 1996-2005 Scientific American
Copyright© Buffalowings.com
Maybe we can apply the same statement to Chemical Synthesis?
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••NSF (CAREER Award)NSF (CAREER Award)••NSFNSF--EPA STAR ProgramEPA STAR Program••ACSACS--PRFPRF••LEQSFLEQSF••NASANASA••Louisiana Center of Excellence (NSFLouisiana Center of Excellence (NSF--EPSCoR)EPSCoR)••DODDOD••NSFCNSFC••JSPS JSPS ••EPAEPA
Prof. Kurt BirdswhitsleProf. Kurt BirdswhitsleProf. Dong WangProf. Dong WangProf. Wenming TangProf. Wenming TangProf. Zhiyong WangProf. Zhiyong WangProf. Wei WuProf. Wei WuProf. Christopher CostellioProf. Christopher CostellioDr. Wenchun ZhangDr. Wenchun ZhangDr. Wensheng XiaDr. Wensheng XiaDr. Jung YangDr. Jung YangDr. Taisheng HuangDr. Taisheng HuangDr. Jianheng ZhangDr. Jianheng ZhangDr. Chunmei WeiDr. Chunmei WeiDr. Mingwen WangDr. Mingwen WangDr. Nan JiangDr. Nan JiangDr. John X. HabermanDr. John X. HabermanDr. William T. Slaven IVDr. William T. Slaven IVDr. Sam YiDr. Sam YiDr. Yue MengDr. Yue MengDr. Xiaogang HuaDr. Xiaogang HuaDr. Charlene KehDr. Charlene KehDr. Ganapathy ViswanathanDr. Ganapathy ViswanathanDr. Sripathy VenkatramanDr. Sripathy VenkatramanDr. Yumei LuoDr. Yumei LuoDr. Dongli ChenDr. Dongli ChenDr. Xiaofan YangDr. Xiaofan YangDr. Xianyong WangDr. Xianyong WangDr. Liang ChenDr. Liang ChenDr. Yuhua ZhangDr. Yuhua ZhangDr. Guojun DengDr. Guojun DengDr. Carolyn ReidDr. Carolyn Reid
Prof. Kurt BirdswhitsleProf. Kurt BirdswhitsleProf. Dong WangProf. Dong WangProf. Wenming TangProf. Wenming TangProf. Zhiyong WangProf. Zhiyong WangProf. Wei WuProf. Wei WuProf. Christopher CostellioProf. Christopher CostellioDr. Wenchun ZhangDr. Wenchun ZhangDr. Wensheng XiaDr. Wensheng XiaDr. Jung YangDr. Jung YangDr. Taisheng HuangDr. Taisheng HuangDr. Jianheng ZhangDr. Jianheng ZhangDr. Chunmei WeiDr. Chunmei WeiDr. Mingwen WangDr. Mingwen WangDr. Nan JiangDr. Nan JiangDr. John X. HabermanDr. John X. HabermanDr. William T. Slaven IVDr. William T. Slaven IVDr. Sam YiDr. Sam YiDr. Yue MengDr. Yue MengDr. Xiaogang HuaDr. Xiaogang HuaDr. Charlene KehDr. Charlene KehDr. Ganapathy ViswanathanDr. Ganapathy ViswanathanDr. Sripathy VenkatramanDr. Sripathy VenkatramanDr. Yumei LuoDr. Yumei LuoDr. Dongli ChenDr. Dongli ChenDr. Xiaofan YangDr. Xiaofan YangDr. Xianyong WangDr. Xianyong WangDr. Liang ChenDr. Liang ChenDr. Yuhua ZhangDr. Yuhua ZhangDr. Guojun DengDr. Guojun DengDr. Carolyn ReidDr. Carolyn Reid
Frank LuFrank LuJianke LiJianke LiTian NguyenTian NguyenZigang LiZigang LiMarcie SolonodzMarcie SolonodzSeema WadhwaSeema WadhwaDat TranDat TranSusannah MarshallSusannah MarshallRoman RajuRoman RajuJay LafleurJay LafleurDaniel KortDaniel KortJunice LeeJunice Lee
Prof. Seung Han LeeProf. Seung Han LeeProf. X. YaoProf. X. YaoProf. Z.P. LiProf. Z.P. LiProf. Clara HerreriasProf. Clara HerreriasProf. Guojun DengProf. Guojun DengDr. Sarim DastgirDr. Sarim DastgirDr. L. FengDr. L. FengDr. Nicolas EghbaliDr. Nicolas EghbaliDr. Rene NguyenDr. Rene NguyenDr.Wenwen ChenDr.Wenwen ChenDr.Rachid SkoutDr.Rachid SkoutPatricia MacleodPatricia MacleodRichard GunnRichard GunnCatherine PerronCatherine PerronL. ZhaoL. ZhaoOlivier BasleOlivier BasleRyan BonfieldRyan BonfieldZdanovich Evguenia Zdanovich Evguenia Heather LanmanHeather LanmanTara YacovotchTara YacovotchVéra Devic GuihoVéra Devic GuihoNadine Borduas Nadine Borduas Lei ZhouLei ZhouHaipeng BiHaipeng Bi
Tulane University McGill University
CollaboratorsCollaborators••Prof. T. H. Chan, McGillProf. T. H. Chan, McGill••Prof. J. Lessard, SherbrookeProf. J. Lessard, Sherbrooke••Prof. Y. Matsumura, JapanProf. Y. Matsumura, Japan••Prof. D. Wang, BeijingProf. D. Wang, Beijing••Dr. R. Varma, US EPADr. R. Varma, US EPA••Prof. M. Tremblay, McGill (Cancer)Prof. M. Tremblay, McGill (Cancer)••Prof. B. JeanProf. B. Jean--Claude McGill (Cancer)Claude McGill (Cancer)••Prof. Ken Itami (Nagoya)Prof. Ken Itami (Nagoya)••Prof. A. Moores, McGillProf. A. Moores, McGill
CollaboratorsCollaborators••Prof. T. H. Chan, McGillProf. T. H. Chan, McGill••Prof. J. Lessard, SherbrookeProf. J. Lessard, Sherbrooke••Prof. Y. Matsumura, JapanProf. Y. Matsumura, Japan••Prof. D. Wang, BeijingProf. D. Wang, Beijing••Dr. R. Varma, US EPADr. R. Varma, US EPA••Prof. M. Tremblay, McGill (Cancer)Prof. M. Tremblay, McGill (Cancer)••Prof. B. JeanProf. B. Jean--Claude McGill (Cancer)Claude McGill (Cancer)••Prof. Ken Itami (Nagoya)Prof. Ken Itami (Nagoya)••Prof. A. Moores, McGillProf. A. Moores, McGill
AcknowledgementsAcknowledgementsAcknowledgementsAcknowledgementsMallory Downie Mallory Downie Pauline Dubois Pauline Dubois Xiaohong LiaoXiaohong LiaoMaxime GiguèreMaxime Giguère--BissonBissonLion Xiaotong SunLion Xiaotong SunSteven Qi Shuai Steven Qi Shuai Camille Correia Camille Correia Xiangyu GuoXiangyu GuoAmy EplingAmy EplingJohan BigenJohan BigenDr. Jun wangDr. Jun wangPeng AiPeng AiTieqiang ZengTieqiang ZengDong JiangDong Jiang
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