A method for efficient and aldehyde-selective Wacker oxidation of aryl-substituted olefins using PdCl_2(MeCN)_2, 1,4-benzoquinone, and t-BuOH in air is described. Up to a 96% yield of aldehyde can be obtained, and up to 99% selectivity can be achieved with styrene-related substrates

Dong, Guangbin

Grubbs, Robert H.

Teo, Peili

Wickens, Zachary K.

English

Caltech Authors - Main

S1 
 
Efficient and Highly Aldehyde Selective Wacker Oxidation 
PEILI TEO
a,b
, ZACHARY K. WICKENS
a
, GUANGBIN DONG
c
 and ROBERT H. 
GRUBBS
a,c
* 
a
 Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, 
California Institute of Technology, Pasadena, CA 91125 
b
 Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, Singapore (627833) 
c
Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, 
TX78712 
 
 
Supporting Information 
 
 
Fig. 1 Phenylacetaldehyde yield as a function of reaction time for styrene Wacker on 0.6 mmol scale. 
S2 
 
 
General procedure: 
All olefin oxidation reactions were carried out under aerobic conditions. PdCl2(MeCN)2, 1, was 
prepared following literature procedures.
1
 Commercial p-benzoquinone from Aldrich was 
recrystallized from i-PrOH prior to usage. All liquid olefins were filtered through a plug of basic 
alumina prior to usage. Methyl-4-vinylbenzoate was filtered through a plug of neutral alumina. 2, 
4-dinitrophenylhydrazine solution was prepared following literature procedures.
2
 
     
1
H and 
13
C NMR spectra were recorded on a Varian 500 MHz spectrometer and High 
resolution mass spectra were provided by the California Institute of Technology Mass 
Spectrometry Facility using JEOL JMS-600H High Resolution Mass Spectrometer. 
     Gas chromatography data was obtained using an Agilent 6850 FID gas chromatography 
system equipped with a HP-5 (5%-phenyl)-methylpolysiloxane capillary column (Agilent). 
Instrument conditions-inlet temperature: 250 
o
C; detector temperature: 250 
o
C; hydrogen flow: 
30 ml/min; air flow: 400 ml/min.; constant col + makeup flow: 25 ml/min. Method: 50
o
C for 2 
min., followed by a temperature increase of 10 
o
C/min. to 115
o
C, hold for 0.5 min., another 
temperature increase of 1
o
C/min. to 125 
o
C, hold for 0.5 min., then a temperature increase of 5 
o
C/min. to 140 
o
C, hold 0.5 min. and a final temperature increase of 60 
o
C/min. to 300 
o
C and 
hold at 300 
o
C for 5 min. (total run time = 30.67 min.). Response factors were collected for 
styrene (1), 2-phenylacetaldehyde (1a) and acetophenone (1b) following literature procedures.
3
 
GC sample preparation: Tridecane (0.00123 mmol, 3 µl) was added to the reaction mixture as 
an internal standard. The mixture was then diluted with diethyl ether (2 ml) and ca. 0.5 ml of the 
resultant mixture was filtered through a plug of silica gel followed by flushing with ethyl acetate 
S3 
 
(ca. 1 ml). GC retention times (min) were as follows: styrene 1 (5.80), phenylacetaldehyde 1a 
(8.37), acetophenone 1b (8.75), 1-octene 12 (4.12) and tridecane (14.35).  
 
Typical procedure for substrates 1-11 
t-BuOH is preheated to 85
o
C before being added (4.8 ml) to 1 (3.9 mg, 15 μmol) and p-
benzoquinone (74.7 mg, 0.69 mmol) in a 20 ml glass vial. H2O (12.2 μL, 0.6 mmol) and olefin 
(0.6 mmol) are then added and the mixture stirred for 60 min at 85
o
C.    
 
Typical procedure for isolation of aldehydes 1a-11a and ketones 1b-11b 
All reaction mixtures were removed from heating and flash frozen at -78
o
C (dry ice/EtOH bath) 
immediately after reaction and warmed to 30
o
C after the mixture was completely frozen. A 
solution of 2, 4-dinitrophenylhydrazine (1.2 eq.) was added to the mixture at 30
o
C and the 
mixture stirred for 1 h at room temperature. H2O (ca. 10 ml) is added to the mixture, stirred for 1 
min. and filtered. The residue is washed with cold H2O (ca. 20 ml). The filtrate and aqueous 
washing is then combined and extracted with methylene chloride five times. The residue is re-
dissolved in the organic extract and the solution dried over Na2SO4, followed by removal of 
solvent under reduced pressure. A crude 
1
H NMR is taken with the solid product to determine 
the ratio of aldehyde to ketone. The material is purified using silica gel chromatography with 3% 
ethyl acetate in hexanes to obtain the aldehyde hydrazone (c) and ketone hydrazone (d) 
respectively. Aldehydes 1c-11c exists as a mixture of E and Z isomers and the isolated yield 
reported is for the combined yield of both isomers. The E and Z isomers of 9c have been isolated 
separately and the 
1
H NMR of each isomer has been taken (vide infra) to prove the presence of 
S4 
 
both isomers in the pure isolated c in each of 1c to 11c. Only NMR data for the major isomer is 
provided. 
         
NMR data for aldehyde hydrazones 1c, 2c, 4c, 9c and ketone hydrazone 1d matched that 
reported in literature
4-15
.  
 
2-methylphenylacetaldehyde-2, 4-dinitrophenylhydrazone, 3c, orange solid, yield: 90%. 
1
H 
NMR: δ 11.04 (s, 1H, NH), 9.12 (d, 1H, J 2.5 Hz), 8.32 (ddd, 1H, J 0.5, 2.5, 9.6 Hz), 7.94 (d, 1H, 
J 9.5 Hz), 7.55 (td, 1H, J 0.5, 5.5 Hz, HC=N), 7.23-2-7.19 (m, 4H), 3.76 (d, 2H, J 5.5 Hz, CH2), 
2.38 (s, 3H, CH3). 
13
C NMR: δ 150.0, 145.3, 138.2, 136.9, 133.9, 131.0, 130.3, 129.8, 129.2, 
127.8, 126.7, 123.7, 116.7, 37.0, 19.8. HR-MS (FAB): calc: 315.1093, found: 315.1108.    
  
4-nitrophenylacetaldehyde-2, 4-dinitrophenylhydrazone, 5c, orange solid, yield: 96%. 
1
H NMR: 
δ 11.13 (s, 1H), 9.13 (d, 1H, J 2.6 Hz), 8.34 (ddd, 1H, J 0.74, 2.6, 9.5 Hz), 8.24 (d, 2H, J 8.7 Hz), 
7.91 (d, 1H, J 9.5 Hz), 7.62 (td, 1H, J 0.8, 5.6 Hz), 7.45 (m, 2H), 3.88 (d, 2H, J 5.5 Hz). 
13
C 
NMR: δ 146.0, 143.9, 142.0, 129.1, 128.9, 126.9, 123.1, 122.4, 115.4, 115.1, 113.6, 37.7. HR-
MS (FAB): calc: 346.0788, found: 346.0781.    
 
3-nitrophenylacetaldehyde-2, 4-dinitrophenylhydrazone, 6c, yellow solid, yield: 96%. 
1
H NMR: 
δ 11.13 (s, 1H, NH), 9.13 (d, 1H, J 2.5 Hz), 8.34 (ddd, 1H, J 0.5, 2.5, 9.6 Hz), 8.19-8.15 (m, 2H), 
7.92 (d, 1H, J 9.5 Hz), 7.64-7.61 (m, 2H), 7.57 (td, 1H, J 0.5, 7.0 Hz, HC=N), 3.89 (d, 2H, J 5.5 
Hz, CH2). 
13
C NMR: δ 148.8, 148.0, 145.1, 138.6, 137.8, 135.4, 130.4, 130.1, 129.5, 124.2, 
123.6, 122.7, 116.7, 38.7. HR-MS (FAB): calc: 346.0788, found: 346.0793.    
S5 
 
 
4-fluorophenylacetaldehyde-2, 4-dinitrophenylhydrazone, 7c, light orange solid, yield: 74%. 
1
H 
NMR: δ 11.06 (s, 1H, NH), 9.13 (d, 1H, J 2.5 Hz), 8.33 (ddd, 1H, J 1.0, 2.5, 9.6 Hz), 7.65 (d, 1H, 
J 9.5 Hz), 7.57 (td, 1H, J 0.5, 6.0 Hz, HC=N), 7.25-7.21 (m, 2H), 7.08-7.03 (m, 2H), 3.74 (d, 2H, 
J 6.0 Hz, CH2). 
13
C NMR: δ 163.3, 150.0, 145.3, 138.3, 131.2, 130.8, 130.3, 123.7, 116.7, 116.2, 
116.0, 38.4. HR-MS (FAB): calc: 319.0842, found: 319.0851.    
 
4-chlorophenylacetaldehyde-2, 4-dinitrophenylhydrazone, 8c, light orange solid, yield: 92%. 
1
H 
NMR: δ 11.07 (s, 1H, NH), 9.13 (d, 1H, J 2.5 Hz), 8.33 (dd, 1H, J 2.5, 9.5 Hz), 7.95 (d, 1H, J 9.5 
Hz), 7.57 (td, 1H, J 0.5, 6.0 Hz, HC=N), 7.35-2-7.32 (m, 2H), 7.21-7.19 (m, 2H), 3.74 (d, 2H, J 
6.0 Hz, CH2). 
13
C NMR: δ 149.6, 145.2, 134.0, 133.5, 130.5, 130.3, 129.6, 129.3, 128.9, 123.7, 
116.7, 38.6. HR-MS (FAB): calc: 335.0547, found: 335.0541.    
 
4-bromophenylacetaldehyde-2, 4-dinitrophenylhydrazone, 9c, light orange solid, yield: 90%. 
1
H 
NMR: major isomer: δ 11.07 (s, 1H), 9.12 (d, 1H, J 3 Hz), 8.33 (ddd, 1H, J 0.5, 2.5, 9.5 Hz), 
7.94 (d, 1H, J 9.5 Hz), 7.57 (td, 1H, J 0.5, 5.8 Hz), 7.50-7.48 (m, 2H), 7.15-7.13 (m, 2H), 3.72 (d, 
2H, J 6 Hz), 2.38 (s, 3H); minor isomer: δ 11.34 (s), 9.16 (d, J 2.5 Hz), 8.38 (ddd, J 0.5, 2.5, 8.4 
Hz), 8.09 (d, J 9.5 Hz), 7.62 (dt, J 1.5, 12.5 Hz), 7.44-2-7.41 (m), 7.14-7.08 (m), 3.67 (d, J 2 Hz). 
  
Methyl 4-(2-oxoethyl)benzoate-2, 4-dinitrophenylhydrazone, 10c, orange solid, yield: 59%. 
1
H 
NMR: δ 11.09 (s, 1H, NH), 9.12 (d, 1H, J 2.5 Hz), 8.33 (ddd, 1H, J 0.5, 2.5, 9.6 Hz), 8.05-8.02 
(m, 2H), 7.94 (d, 1H, J 9.5 Hz), 7.61 (td, 1H, J 0.5, 5.5 Hz, HC=N), 7.36-7.33 (m, 2H), 3.92 (s, 
3H, CH3), 3.82 (d, 2H, J 5.5 Hz, CH2). 
13
C NMR: δ 166.9, 149.2, 145.2, 140.9, 138.4, 130.7, 
S6 
 
130.4, 130.3, 129.5, 129.3, 123.6, 116.8, 52.4, 39.2. HR-MS (FAB): calc: 359.0992, found: 
359.0980.    
 
2-(3, 5-bis(trifluoromethyl)phenyl)acetaldehyde-2, 4-dinitrophenylhydrazone, 11c, yellow solid, 
72%. %. 
1
H NMR: δ 11.15 (s, 1H, NH), 9.13 (d, 1H, J 2.5 Hz), 8.34 (dd, 1H, J 2.5, 9.5 Hz), 7.89 
(d, 1H, J 9.5 Hz), 7.84 (s, 1H), 7.75 (s, 2H), 7.64 (t, 1H, J 5.5 Hz, HC=N), 3.92 (d, J 5.5 Hz, 
CH2). 
13
C NMR: δ 147.3, 145.1, 138.2, 132.6, 132.3, 130.4, 129.6, 124.4, 123.6, 122.3, 121.6, 
116.7, 38.7. HR-MS (FAB): calc: 437.0684, found: 437.0706.    
 
4-methylacetophenone-2, 4-dinitrophenylhydrazone, 2d, red solid. 
1
H NMR: δ 11.36 (s, 1H, 
NH), 9.17 (d, 1H, J 2.5 Hz), 8.36 (ddd, 1H, J 0.5, 2.5, 9.75 Hz), 8.13 (d, 1H, J 9.5 Hz), 7.77-7.75 
(m, 2H), 7.27-7.26 (m, 2H), 2.45 (s, 3H, CH3), 2.42 (s, 3H, CH3). 
13
C NMR: δ 152.7, 145.2, 
140.7, 138.3, 134.7, 130.3, 129.8, 129.6, 126.7, 123.8, 117.0, 21.6, 13.9. HR-MS (FAB): calc: 
315.1093, found: 315.1087.    
 
2-methylacetophenone-2, 4-dinitrophenylhydrazone, 3d, light orange solid. 
1
H NMR: δ 11.29 (s, 
1H, NH), 9.17 (d, 1H, J 3.0 Hz), 8.32 (ddd, 1H, J 0.5, 2.5, 9.5 Hz), 8.01 (d, 1H, J 9.5 Hz), 7.37-
7.28 (m, 4H), 2.48 (s, 3H, CH3), 2.46 (s, 3H, CH3). 
13
C NMR: δ 157.7, 155.2, 148.6, 145.3, 
144.9, 138.7, 138.4, 137.8, 135.9, 134.2, 131.6, 131.5, 130.38, 130.35, 130.2, 130.1, 129.8, 
129.4, 129.1, 128.5, 127.5, 126.3, 126.2, 123.7, 116.9, 116.7, 116.5, 24.9, 21.2, 19.2, 17.8. HR-
MS (FAB): calc: 315.1093, found: 315.1104. cis and trans isomers for 3d exists in 3:1 mixture 
resulting in complicated 
13
C NMR.     
 
S7 
 
4-tert-butylacetophenone-2, 4-dinitrophenylhydrazone, 4d, light orange solid. 
1
H NMR: δ 11.36 
(s, 1H, NH), 9.17 (d, 1H, J 2.5 Hz), 8.36 (ddd, 1H, J 0.5, 2.5, 9.5 Hz), 8.13 (d, 1H, 9.5 Hz), 7.82-
7.79 (m, 2H), 7.50-7.47 (m, 2H), 2.46 (s, 3H, CH3), 1.36 (s, 9H, C(CH3)3). 
13
C NMR: δ 153.9, 
152.7, 145.2, 138.3, 134.7, 130.3, 129.8, 126.5, 125.9, 123.8, 117.0, 35.1, 31.4, 13.9. HR-MS 
(FAB): calc: 357.1563, found: 357.1565.    
 
4-nitroacetophenone-2, 4-dinitrophenylhydrazone, 5d, intense orange solid. 
1
H NMR: δ 11.45 (s, 
1H, NH), 9.20 (d, 1H, J 2.5 Hz), 8.43 (dd, 1H, J 2.5, 9.5 Hz), 8.33-8.30 (m, 2H), 8.14 (d, 1H, J 
9.5 Hz), 8.04-8.01 (m, 2H), 2.52 (s, 3H, CH3). 
13
C NMR: δ 149.5, 148.6, 144.8, 143.3, 139.3, 
130.6, 130.5, 127.4, 124.2, 123.6, 117.0, 13.9. HR-MS (FAB): calc: 346.0788, found: 346.0793.    
 
3-nitroacetophenone-2, 4-dinitrophenylhydrazone, 6d, intense orange solid. 
1
H NMR: δ 11.45 (s, 
1H, NH), 9.20 (d, 1H, J 2.5 Hz), 8.43 (dd, 1H, J 2.5, 9.5 Hz), 8.33-8.30 (m, 2H), 8.14 (d, 1H, J 
9.5 Hz), 8.04-8.01 (m, 2H), 2.52 (s, 3H, CH3). 
13
C NMR: δ 149.5, 148.9, 144.9, 139.2, 139.1, 
132.2, 130.6, 130.4, 130.0, 124.6, 123.7, 121.6, 117.0, 13.9. HR-MS (FAB): calc: 346.0788, 
found: 346.0777. 
 
4-fluoroacetophenone-2, 4-dinitrophenylhydrazone, 7d, intense orange solid. 
1
H NMR: δ 11.43 
(s, 1H, NH), 9.19 (d, 1H, J 2.5 Hz), 8.70 (t, J 2 Hz), 8.44 (ddd, 1H, J 0.5, 2.5, 9.25 Hz), 8.31 
(ddd, 1H, J 1.0, 2.5, 8.25 Hz), 8.21 (ddd, 1H, J 1.0, 2.0, 7.75), 8.15 (d, 1H, J 9.5 Hz), 7.66 (t, 1H, 
J 8.0 Hz), 2.53 (s, 3H, CH3). 
13
C NMR: δ165.2, 151.4, 145.2, 138.5, 133.6, 130.4, 128.7, 123.8, 
116.9, 116.1, 115.9, 14.0. HR-MS (FAB): calc: 319.0842, found: 319.0843.    
 
S8 
 
4-chloroacetophenone-2, 4-dinitrophenylhydrazone, 8d, intense orange solid. 
1
H NMR: δ 11.37 
(s, 1H, NH), 9.18 (d, 1H, J 2.5 Hz), 8.38 (dd, 1H, J 2.0, 9.5 Hz), 8.11 (d, 1H, J 9.5 Hz), 7.88-7.85 
(m, 2H), 7.17-7.13 (m, 2H), 2.46 (s, 3H, CH3). 
13
C NMR: δ 151.2, 145.1, 138.6, 136.5, 135.9, 
130.4, 130.0, 129.2, 128.0, 123.7, 116.9, 13.8. HR-MS (FAB): calc: 335.0547, found: 335.0560.    
 
4-bromoacetophenone-2, 4-dinitrophenylhydrazone, 9d, intense orange solid. 
1
H NMR: δ 11.36 
(s, 1H, NH), 9.18 (d, 1H, J 2.5 Hz), 8.38 (dd, 1H, J 2.5, 9.5 Hz), 8.11 (d, 1H, J 9.5 Hz), 7.75-7.72 
(m, 2H), 7.61-7.57 (m, 2H), 2.45 (s, 3H, CH3). 
13
C NMR: δ 151.2, 145.1, 138.6, 136.4, 132.1, 
130.4, 130.1, 128.2, 124.8, 123.7, 116.9, 13.8. HR-MS (FAB): calc: 379.0042, found: 379.0056.    
 
Methyl 4-acetylbenzoate-2, 4-dinitrophenylhydrazone, 10d, orange solid. 
1
H NMR: δ 11.40 (s, 
1H, NH), 9.18 (d, 1H, J 2.5 Hz), 8.40 (dd, 1H, J 2.0, 9.5 Hz), 8.16-8.10 (m, 3H), 7.94-7.92 (m, 
2H), 3.96 (s, 3H, CH3), 2.49 (s, 3H, CH3). 
13
C NMR: δ 166.7, 151.1, 145.0, 141.5, 138.8, 131.4, 
130.4, 130.1, 126.6, 123.7, 117.0, 115.5, 52.6, 13.9. HR-MS (FAB): calc: 359.0992, found: 
359.1005.    
 
3, 5-bis(trifluoromethyl)acetophenone-2, 4-dinitrophenylhydrazone, 11d, light orange solid. 
1
H 
NMR: δ 11.44 (s, 1H, NH), 9.20 (d, 1H, J 2.5 Hz), 8.46 (ddd, 1H, J 0.5, 2.5, 9.6 Hz), 8.27 (s, 
2H), 8.12 (d, J 9.5 Hz), 7.95(s, 1H), 2.53 (s, 3H, CH3). 
13
C NMR: δ 148.7, 144.8, 139.6, 139.3, 
132.6, 132.4, 130.7, 126.5, 124.4, 123.6, 122.2, 117.0, 13.9. HR-MS (FAB): calc: 437.0684, 
found: 437.0684.    
 
S9 
 
               (1) Heck, R. F. Palladium Reagents in Organic Synthesis: Best Synthetic Methods; Academic 
Press: New York, 1985. 
 (2) McMurry, J. E. J. Am. Chem. Soc. 1968, 90, 6821. 
               (3) Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 
5740. 
 (4) Agrawal, M. K.; Ghosh, P. K. J. Org. Chem. 2009, 74, 7947. 
               (5) Yoshimura, A.; Banek, C. T.; Yusubov, M. S.; Nemykin, V. N.; Zhdankin, V. V. J. Org. Chem. 
2011, 76, 3812. 
 (6) Matsuo, J.-i.; Iida, D.; Tatani, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 223. 
 (7) Fox, R. J.; Lalic, G.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 14144. 
 (8) Miiller, S.; Schmidt, R. R. Helv. Chim. Acta 1993, 76, 616. 
 (9) Clyne, D. S.; Weiler, L. Tetrahedron 1999, 55, 13659. 
 (10) MacMillan, J. B.; Molinski, T. F. J. Am. Chem. Soc. 2004, 126, 9944. 
 (11) Jacob, P. J. Organomet. Chem. 1978, 156, 101. 
 (12) Critch, S. C.; Fallis, A. G. Can. J. Chem. 1977, 55, 2845. 
 (13) Chauvet, F.; Heumann, A.; Waegell, B. J. Org. Chem. 1987, 52, 1916. 
 (14) Mascal, M.; Nikitin, E. B. Angew. Chem. Intl. Ed. 2008, 47, 7924. 
               (15) Dydio, P.; Dzik, W. I.; De-Bruin, B.; Reek, J. N. H.; Lutz, M. Angew. Chem. Intl. Ed. 2011, 
50, 396. 
 
S10 
 
3c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N
N
H
NO2
NO2
S11 
 
3c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S12 
 
5c
N
N
H
NO2
NO2
O2N
S13 
 
5c
S14 
 
6c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH
O2N
NO2
O2N
S15 
 
6c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S16 
 
7c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH
O2N
NO2
F
S17 
 
7c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S18 
 
8c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH
O2N
NO2
Cl
S19 
 
8c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S20 
 
10c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH
O2N
NO2
MeO2C
S21 
 
10c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S22 
 
11c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH
O2N
NO2
F3C
F3C
S23 
 
11c 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S24 
 
2d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
S25 
 
2d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S26 
 
3d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
S27 
 
3d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S28 
 
4d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
S29 
 
4d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S30 
 
5d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
O2N
S31 
 
5d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S32 
 
6d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
O2N
S33 
 
6d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S34 
 
7d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
F
S35 
 
7d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S36 
 
8d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
Cl
S37 
 
8d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S38 
 
9d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
Br
S39 
 
9d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S40 
 
10d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
MeO2C
S41 
 
10d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
S42 
 
11d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
N NH NO2
NO2
F3C
F3C
S43 
 
11d 
 
 
 
 
 
 
 
 
 
 
 
 
 
 


Efficient and Highly Aldehyde Selective Wacker Oxidation

https://authors.library.caltech.edu/32960/2/ol301240g_si_001.pdf

Efficient and Highly Aldehyde Selective Wacker Oxidation

Abstract

Similar works

Full text

Available Versions

Caltech Authors - Main

Caltech Authors - Main