"Hidden Gems" in Chemistry Letters
Baran Group Meeting
04/17/2010
Chemistry Letters (1972-2010):
Jun Shi
Cl
5. Chem. Lett., 1976, 47
• founded in 1972
• published by The Chemical Society of Japan monthly
• first Editor-in-Chief: Teruaki Mukaiyama (633 papers)*
• Tamejiro Hiyama: current editor-in-chief since 2003
• 39 volums, 461 issues, 22,143 papers
• covers all areas of chemistry
• highligh reviews since 2004
• 1.504-impact factor in 2008
Cl
O
tBuOK
PhNCO
Br
N
H
proposed mechanism
in this paper:
O
-50°C
O
78%
N
O
N
Ar
O
N
Ph
NHAr
6. Chem. Lett., 1977, 471
1. Chem. Lett. 1972, 373/1972, 401
NH2
HS-CH2-CO2Et
O
MeOH
N
H
CO,Se, Et3N, R.T.
Et2N
NEt2
CO, Se, heat
2. Chem. Lett., 1973, 91 first example of phenylation of nitro-olefin
H
Pd(OAc)2
Ph
H
Ph
CN Cl CCOOH
3
Me
CN
NNHTs
R
H
NO2
NaOH
N N
NNHTs
PhN2Cl
Ar
4. Chem. Lett., 1975, 1333
NH2
Bu3Sn
N NPh
Ph
THF, Et3N
reflux
Ar
Ph
NaCO2CF3
Me
DMF, 170°C
9. Chem. Lett. 1977, 569
CO2Me
O
MeOH
NPh
N
Me
Cl
isoamyl nitrite
tBuCO2H
60°C
CN
CN
Cl
Ph
Me
F F
O
O MeOH:AcOH
OH
5:1
hν
hν
O
O
10. Chem. Lett., 1980, 825
CH2
CH2
Me
then ClCO2Et
8. Chem. Lett., 2005, 1440, 34(10)
70%
Benzene
Ph
NO2
reflux
3. Chem. Lett., 1973, 1071 synthesis of 2,5-disubstituted tetrazole
H
CO2Et
7. Chem. Lett., 1977, 553
Et2NH
Ph
" S-CH-CO Et "
2
OMe
O
THF
O
2 eq LDA
Me
65%
OH
4-C6H4-Cl
MeHN
O
ArCH2NH2
*No Prof. Mukaiyama's chemsitry in Chem. Lett. is included here. Please see Yoshi's GM on Mukaiyama instead FIY.
N
air
O
cat.
ArCHO
1
Baran Group Meeting
04/17/2010
"Hidden Gems" in Chemistry Letters
11. Chem. Lett., 1982, 1933
NC
CN
MeS
H2 N
LDA, 60%
17. Chem. Lett. 1987, 1145
O
FCl2CCO2Me
CN
N
R1
NEt2
NC
S
NEt2
Me
O
NHCOPh
S
Me
Me
SnBu3
+
Me
SnBu3
Pd(OAc)2
R
EtO2C
Ph
R1
14. Chem. Lett., 1987, 809
CONHPh
PhS
15. Chem. Lett., 1987, 859
CONHPh
PhS
E+
Tol. reflux
84.3%
21. Chem. Lett., 1988, 589
NHBz
DBU
thenBzCl
RMgBr
OTf
3 eq BuLi
CO2Et
CO2Et
Me Me SPh
"Selenium Polonovski Reaction"
CO2Et
PhSeOTf
O-
20 Chem. Lett., 1987, 1575
tBuOOH
PhS
R2
Me
N+
+
R1
Rh2(OAc)4
N2
SPh
19. Chem. Lett., 1987, 1575
13. Chem. Lett., 1987, 5
R
Me
Ph
N
PPA
120°C
Zn(cat)-CuCl
CO2Me
18. Chem. Lett., 1987, 1569
NEt2
12.Chem. Lett., 1985, 291
O
R2
F
Jun Shi
Li2MnCl4 cat.
R1
R
"synthesis of diamond by CO and H2"
E
RhCl(CO)(PMe3)2
R
R
CO, hν
16. Chem. Lett., 1987, 899
CO2Me
N
tBu
tBu
N
CO2Me
TsOH
Bezene, reflux
tBu
N
CO2Me
tBu
2
Baran Group Meeting
04/17/2010
"Hidden Gems" in Chemistry Letters
22. Chem. Lett., 1990, 1125
OH
Ar
27. Chem. Lett., 1997, 55
O
TsNCl2
R
R
Ar
MeCN, 35°C
23. Chem. Lett., 1992, 1161 "Transhydroxylation"
Ac
P(nBu)3-CCl4
N
R
NC
CN
R2OH
NC
H
HO
R
O
R
NC
OMe
CN
R2OH
O
R
SiMe2Ph
O
Me
Me
Me
OEt
Ph
25. Chem. Lett., 1995, 679
O
R
R = alkyl, SiR3
Me
Ph
Me
OMe
OMe
R
Ru(H)2(CO)(PPh3)3 R'
cat.
R
OMe
CoCl2(dpph) cat
TMSCH2MgCl
Ph
(3 eq)
O
26. Chem. Lett., 1995, 681
O
85%
R
O
TMS
ether, 20°C, 35h
OMe
Ru(H)2(CO)(PPh3)3
cat.
O
CoCl2(dpph) cat
TMSCH2MgCl
OMe (1.5 eq)
Ph
75%
SiMe2Ph
40%-99%
OR2
30. Chem. Lett., 2004, 832, 33(7)
Me
EtO2C
SnCl4, R.T.
O
O
99-54%
OR2
CN
cat.
O
24. Chem. Lett., 1994, 627
CN
OH
75.6%
N
MeCN, R.T
HO
NC
cat.
O
Cl
Ac
Jun Shi
ether, reflux, 48h
TMS
90%
TMS
31. Chem. Lett., 2005, 194, 34(2)
O
MnO2, CHCl3
reflux
X
R'
O
R, R = alkyl, SiR3
Me
O Ru(H)2(CO)(PPh3)3
cat.
S
Ph
O
SiMe3
90%
32. Chem. Lett., 2006, 714, 35(7)
Cu(hfa)2 cat
PhSiH3 + ROH
O
O
Me
S
SiMe3
Ph
F3C
hfa
PhSiH2OR
CF3
3
"Hidden Gems" in Chemistry Letters
Baran Group Meeting
04/17/2010
37. Chem. Lett., 2008, 1006
33. Chem. Lett., 2007, 1414, 36 (12)
OH
Ar
O
O2
Ar
Actived Carbon
Ar'
F
F3 C
Ar'
O
+
Ph
F3 C
N
1) TMSOTf
2) TiCl4,
O
F
F
Cl
O
O
Ar
60-79%
Ph
S+
O
S+
Me
H
Ph Si
Tf2O Ar
2,6-di-tBuPyr.
Ph
-O
S
ArH
S
N
35. Chem. Lett., 2007, 366, 36(3)
O
B
O
-O
O
Ar
F
[RhCl(cod)2]2
38. Chem. Lett., 2008, 786
34. Chem. Lett., 2007, 36(5), 636
O
Jun Shi
S
Ph
SMe
Me
S
Me
Me
SMe
2,6-di-tBuPyr.
OSi
Tf2O
H
62%
RhCl(PPh3)4
1,2-reduction
40. Chem. Lett., 2009, 38(1), 46
H
O
CO2Me
PdCl2, CuCl, CO/O2
Ph Si
OSi
H
CO2Me
MeOH
O
75%
RhCl(PPh3)4
41. Chem. Lett., 2009, 38(2), 116
1,4-reduction
36. Chem. Lett. 2007, 52, 36(1)
R1
Rh2(OOCCF3)4 cat
R2
N
60°C
R1
R2
N
H
Ts
N
NiCl2dppe
CH2(ZnI)2
I
Acetone
SiMe3
Ts
N
Me
H2C
Me
Si O
Me Me
86%
4
Baran Group Meeting
04/17/2010
"Hidden Gems" in Chemistry Letters
Selected Total Syntheses:
42. Chem. Lett. 2009, 38(3), 204
O
1. Chem. Lett., 1990, 1230
R
RNC, Pd(PPh3)4
O
OMe
N
CO2Me
CO2Me
Ar
75-96%
Ar
Me
43. Chem. Lett. 2009, 38(7), 710
OMe Ni(cod)2/L
NaOtBu
R
Jun Shi
MeO
OBn
OBn
O
O
O
NR1R2
R
NHR1R2
MeO
OMe
250°C
O
NBn
OBn
OMe
42-89%
OMe
OMe
OMe
44. Chem. Lett. 2009, 38(5), 430
OBn
H2O2
R
CHO
R
CO2H
Pd(TFA)2
N
Bn H
45. Chem. Lett. 2009, 38(5), 484
Het-CO2R
Thiamine hydrochloride
Het: pyridines, quinolines, quinoxaline
46. Chem. Lett. 2009, 488
O
2. Chem. Lett., 2004, 942
Thiamine hydrochloride
OH
MeO2C
O
O
O
H
OTHP
H
X=F
Si
Me
H
nBuSnH
88%
OH
47. Chem. Lett. 2009, 38(6), 352
Ar
OH
O
EtO2C
O
TEMPO
NaOCl, KBr
OH
H
H
H
THPO
93 ee%, 71%
N2
Me
O
Mn(pic)3
O
O
MeO2C
N
Bn H
O
(-)-Mesembrine
Et3N, ROH
Het-CHO
O
H
OCO2Et
Pd(PPh3)4
NaH
H
Me
Ar
Si
Me
OH
74-99%
H
OHC
CO2H
Sordarincin
H
CO2Et O
5
"Hidden Gems" in Chemistry Letters
Baran Group Meeting
04/17/2010
Selected Reviews:
1. Carotenoid Radicals: Cryptochemistry of Natural Colorants
3. Chem. Lett., 2007, 10
MeO
HO
CHO
Jun Shi
MeO
O
MeO
MeO
2. Formation of C–C Bonds via Ruthenium-catalyzed Transfer Hydrogenation:
Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level 2008, 1102
O
Me
MeO
Br
O
MeO2C
2010,148
O
O
3. Synthesis of Biologically Active Carbazole Alkaloids Using Selective
Transition-metal-catalyzed Coupling Reactions 2009, 8
4. Participation of Geminal Bonds in Organic Reactions 820, 2007
DTBMP
200°C
MeO
O
O
O
O
200, 2007
6. Alkyl Phosphinites: Versatile Synthetic Intermediates for Dehydration
Condensation Reactions 2, 2007
7. Transition Metal-catalyzed Carbochalcogenation of Alkynes 1320, 2006
OMe
O
AlCl3
100°C
O
CO2Me
824, 2006
Me
OH
O
Me
OH
O
8. Cycloaddition Reactions of Transition Metal-containing Benzopyrylium and
Related Zwitterionic Intermediates 1082, 2006
9. The Tishchenko Reaction: A Classic and Practical Tool for Ester Synthesis
74%
O
HO
HO2C
OMe
O
Me
O
HO
5. Catalytic Direct Arylation of Heteroaromatic Compounds
Me
MeO
MeO2C
40%
O
CO2H
vinaxathone
10. Ruthenium-catalyzed Reconstructive Synthesis of Functional Organic
Molecules via Cleavage of Carbon–Carbon Bonds 1462, 2005
11. Azide Compounds: Nitrogen Sources for Atom-efficient and Ecologically
Benign Nitrogen-atom-transfer Reactions 1304, 2005
12. Transition Metal-catalyzed Reactions Using Alkynes as Precursors of
Carbene and Vinylidene Complexes 1068, 2005
13. Advances in Iron Catalyzed Cross Coupling Reactions 624, 2005
14. Iminium Alkaloids from Marine Invertebrates: Structure, Biological Activity,
and Biogenesis 454, 2005
15. !Sulfoximines: Synthesis and Catalytic Applications 482, 2004
16. Palladium Catalyzed Aerobic Dehydrogenation: From Alcohols to Indoles
and Asymmetric Catalysis 362, 2004
6