the career of chao-jun li guochang 2010.7.. b.s. zhengzhou university 1979 m.s. chinese academy of...
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The Career of Chao-Jun Li
Guochang
2010.7.
B.S. Zhengzhou University 1979 M.S. Chinese Academy of Science 1985 Tak-Hang Chan
Ph.D. McGill University 1989 Tak-Hang Chan and David N. Harpp
Post-Doctoral, Stanford University 1992 B. M. Trost
Tulane University, USA
Assistant Professor 1994Professor of Chemistry 2000
McGill University, Canada
Professor of Chemistry 2003
Research Interests
various copper, silver, and gold-catalyzed aldehyde-alkyne-amine (A3)coupling and asymmetric aldehyde-alkyne-amine (AA3) coupling reactions
Acc. Chem. Res. 2010, 43, 581
various Grignard-type reactions in aqueous media Tetrahedron,1996, 52, 5643
Cross-Dehydrogenative Coupling
Acc. Chem. Res.2009, 42, 335
Cross-Dehydrogenative Coupling
PhN
Ph
74% yield
PhN
CH2OH
40% yield
PhN
12% yield
NPh
Ph
36% yield
NOMe
Ph
74% yield
Jacs, 2004, 126, 11810-11811
N+ Ph
CuOTf+ ligand
TBHP50oC, 2 days
N
Ph
Y 67%, ee 63%
ligand
O
N N
O
Ph Ph
N
TMS
N
hex
N
hex
Y 11%, ee 30% Y 65%, ee 26% Y 48%, ee 5%
OMe
OL, 2004, 6, 4997
sp3-sp2 Coupling
NPh
+NH
5 mol% CuBr1.3 eq, TBHP
50oC
NPh
NHY 85%
NPh
NH
Y 57%
MeO
NPh
NH
Y 61%
NPh
NH
Y 63%
MeOOC
NPh
Y 77%
NH
NPh
N
Y 44%
Jacs. 2005, 127, 6968-6969
PNAS. 2006, 103, 8928–8933.
sp3-sp3
Jacs. 2005, 127, 3672-3673
Eur. J. Org. Chem. 2005, 3173–3176
Green Chem., 2007, 9, 1047–1050
NPh
+B(OH)2 CuOTf(20 mol %)
T-HYDRO, DME, 50oC
NPh
Ph
Y 50% ee 44%
NO
N N
O
Ph Ph
OL, 2008, 10, 3661
NPh
+
CuBr(5 mol %)
O2, MeOH, 60oCN
Ph
P(OMe)2
Y 79%
P(OMe)2
O
H
O
Chem. Commun., 2009, 4124–4126
NH
O
O
O+
COOEt
COOEt
cat, Cs2CO3
toluene, 150oC NH
O
O
O
CH(COOEt)2N N
CuOAcAcO
O
NH
O
O
O
CH(COOEt)2
NH
O
O
O
C(COOEt)2
NH
O
O
O
C(COOEt)2
Y 84%
Y 73% Y 48% NR
Angew. Chem. Int. Ed. 2008, 47, 7075 –7078
NH
HN
O
MeO
+B(OH)2
10 mol% CuBr1.0 equiv TBHP
DCE, 100oC NH
HN
O
MeOPh
Y 81%
NH
PMPHN
O
PMP
Y 71%
NH
PMPHN
O
S
Y 84%
NH
PMP O
O
Ph
ND
NH
PMP N
O
PMP
ND
PNAS, 2009, 106, 4106-4111
O+
O
DDQ
100oCO
O
Ph
Y 71%
O
O
Ph
Y 75%
O
O
76%
O
O
Ph
59%
Jacs, 2006, 128, 4242-4243
O+
InCl3/Cu(OTf)2
rt, DDQ
COOMe
COOMeO
CH(COOMe)2
Y 77%
O
C(COOMe)2
Y 53%
OO
CH(COOMe)2NO2
O
Ph
Y 72% Y 17%
Angew. Chem. Int. Ed. 2006, 45, 1949 –1952
+
OO CuBr/ CoCl2TBHP
80oC
OO
Y 71%OO
OO OO
31% 41% 41%
DD
D
D +OO standard conditons
55%
OO
D
DD
D
DD
DD O
O
+
1:1
J. AM. CHEM. SOC. 2006, 128, 56-57
Ph Ph + Ph
O O FeCl2tBuOOtBu
80oC Ph Ph
O
Ph
O
Y 66%O
Ph
O
Ph
MeO
Y 64%
O
PhO
Ph
Y 67%
Ph
OO
Y 85%
Angew. Chem. Int. Ed. 2007, 46, 6505 –6507
O
OPh
O
Y 82%
O
OO
Ph
Y 38%
O
O
Ph
O
O
O
Ph
O
1:2
Y 46%
Eur. J. Org. Chem. 2007, 4654–4657
Ph
OO
Ph
Y 27%
OMe
Ph
O
Ph
O
Y 71%
Ph
O
Ph
O
Y 83%
OMe
N
O
O
OH
NHPI
Tetrahedron Letters, 51 (2010) 1172–1175
Chem. Eur. J. 2009, 15, 333 – 337
N+
O-
+tBuOOtBu
135oC
N+
O-N+
O-
Y 70% 3.5:1
N+
O-
N+
O-
Ph
Y 65% Y 75%
N+
O-
O
OO
ON+
O-
O
OO
O
O
O
Y 61%2.2 : 1
Ph
NPh
+tBuOOtBu
135oCPh
HNPh
Y 96%
HNPh
O
Y 84%
Ph
HNPh
Ph
HNPh
Y 60% Y 37%
Tetrahedron Letters, 2008, 49, 5601–5604
Jacs, 2008, 130, 2900-2901
NN
Y 42%
trace1:1
Y 80%
NN
Y 48%
traceOMe
OMe
Angew. Chem. Int. Ed. 2008, 47, 6278 –6282
Adv. Synth. Catal. 2009, 351, 2071 – 2074
Ph O+ EtOOC NH2 HCl
CuI,AgIO3
Cs2CO3, T-HYDRO 80oC
Ph NH
O
COOEt
Y 93%
Ph NH
O
NH
O
COOEtPh NH
O
Ph
Y 91% Y 71% Y 39%
Jacs, 2006, 128, 13064-13065TL, 2007, 48, 1033–1035
Y = 57%- 91%
OO+
AuBr3 / AgSbF6
CH2Cl2
OO
74%
OO
O O
OPh
Ph
O
Y 44% Y 70% Y 81%
Jacs, 2004, 126, 6884-6885
Jacs, 2005, 127, 17184-17185
NCOOH
Ph
+ Ph
NN
CuBr,tBuOOtBu 110oC
N
Ph
Ph
Y 90%
N
Ph
Ph Ph
Y 56%
NPh
Y 74%
NBn
Bn
Y 20%
N
Ph
NH
Y 74%
NH
N
PhY 63%
N
Ph
NO2
Y 86%
NPh
NO2
Y 81%
Ph N
Ph
Ph
Y 78%
NPh
COOEt
Y 67%
NPh
COOEt
Y 64% (dr 1.5:1)
J. Org. Chem. 2010, 75, 783–788
Chem. Commun., 2010, 46, 4184–4186