Apr 17, 2010 - OTf. RMgBr. Li2MnCl4 cat. R1. R. +. "Hidden Gems" in Chemistry Letters .... The Tishchenko Reaction: A Cl
"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
