Direct Electrochemical Cross-Coupling
J . Org. Chem., Vol. 61, No. 5, 1996 1755
(3H, s), 3.77 (2H, s), 3.89 (3H, s), 7.27 and 8 (2H each, AA′-
BB′ system J ) 8.2 Hz); 13C NMR (CDCl3, 50.3 MHz) 29.2 (1C,
CH3), 50.2 (1C, CH2), 51.7 (1C, CH3), 128.6 (1C, arom), 129.2
(2C, arom), 129.6 (2C, arom), 139.1 (1C, arom), 166.4 (1C, CO2),
204.8 (1C, CO); MS 192 (M), 161 (M - 31), 149 (M - 43, base),
135 (M - 57), 118 (M - (31 + 43)), 90.
(22);39 benzeneacetic acid, R-methyl-3-(trifluoromethyl)-methyl
ester (23);40 benzeneacetic acid, R-methyl-4-(trifluoromethyl)-
methyl ester (24);40 benzeneacetic acid, 4-cyano-methyl ester
(25);8 benzeneacetic acid, 4-cyano-R-methyl-methyl ester (26);41
benzeneacetic acid, 4-(dimethylamino)-methyl ester (27);42
benzeneacetic acid, R-methyl-4-methyl-methyl ester (28);39
4-methoxybenzeneacetic acid, R-methyl-methyl ester (29);39
1-naphthylacetic acid, R-methyl-methyl ester (30);43 [2-(6-
methoxynaphthyl)]acetic acid, R-methyl-methyl ester (31);44
3-butenoic acid, 4-phenyl-methyl ester (32);45 3-butenoic acid,
2-methyl-4-phenyl-methyl ester (33);8 1-(2-propenyl)-3-(tri-
fluoromethyl)benzene (34);46 1-(2-propenyl)-4-(trifluorometh-
yl)benzene (35);47 1-(2-butenyl)-4-methoxybenzene (37a );3a
1-methoxy-4-(1-methyl-2-propenyl)benzene (37b);48 benzene,
1-fluoro-4-(phenylmethyl) (39);49 thiophene, 2-(phenylmethyl)
(40);50 benzenepropanoic acid, methyl ester (41);51 benzene,
1-(1-propenyl)-3-(trifluoromethyl) (42);46 benzonitrile, 4-(1-
propenyl) (43).52
3-(3-Acetylp h en yl)-2-bu ta n on e (14): 1H NMR (CDCl3, 200
MHz) δ 1.43 (3H, d, J ) 6.99 Hz), 2.09 (3H, s), 2.62 (3H, s),
3.89 (1H, q, J ) 6.99 Hz), 7.45-7.51 and 7.86-7.91(4H, m);
13C NMR (CDCl3, 50.3 MHz) δ 17.0 (1C, CH3), 26.3 (1C, CH3),
28.2 (1C, CH3), 53.0 (1C, CH), 127.1 (1C, arom), 127.4 (1C,
arom), 129 (1C, arom), 132.1 (1C, arom), 137.5 (1C, arom), 141
(1C, arom), 197.4 (1C, CO), 207.7 (1C, CO); high resolution
MS 190.1 (M), 175.1 (M - 15), 148.1 (M - 43), 105.1, 43.0
(base).
Ben zen ea cetic a cid , 4-flu or o-m eth yl ester (21): 1H
NMR (CDCl3, 200 MHz) δ 3.59 (2H, s), 3.69 (3H, s), 6.96-
7.04 (2H, m), 7.20-7.27 (2H, m); 19F NMR (CDCl3, 188.3 MHz):
δ -115.52 (1F, m)/CFCl3; MS 168 (M), 109 (M - 59, base).
2-[3-(Tr iflu or om eth yl)p h en yl]p r op ion on itr ile (38): 1H
NMR (CDCl3, 200 MHz) δ 1.64 (3H, d, J ) 7.3 Hz), 4.02 (1H,
q, J ) 7.3 Hz), 7.47-7.66 (4H, m); 13C NMR (CDCl3, 50.3 MHz)
δ 20.9 (1C, CH3), 30.9 (1C, CH), 120.9 (1C, CN), 123.5 (1C,
arom, q, J CCCF ) 3.78 Hz), 123.8 (1C, CF3, q, J CF ) 272.33 Hz),
124.9 (1C, arom, q, J CCCF ) 3.72 Hz), 129.7 (1C, arom), 130.2
(1C, arom), 131.3 (1C, arom, q, J CCF ) 32.48 Hz), 138.3 (1C,
arom); 19F NMR (CDCl3, 188.3 MHz) δ -62.66 (3F, s)/CFCl3;
high resolution MS 199.1 (M), 184.1 (M - 15, base), 145.1,
130.1 (M - 69).
The following products were characterized by comparison
of their GC and spectral data with those for commercially
available samples: 1-phenyl-2-propanone (1); 1-(4-fluorophen-
yl)-2-propanone (2); 1-[3-(Trifluoromethyl)phenyl]-2-propanone
(3); 1-(4-methoxyphenyl)-2-propanone (6); methyl phenylac-
etate (19); 1-methoxy-4-(2-propenyl)benzene (36); benzene,
1-methoxy-4-(1-propenyl) (44).
The following compounds were identified by comparison of
their physical and spectral data with those given in the cited
references: Benzoic acid, 2-(2-oxopropyl)-methyl ester (4a );30
3-methylisocoumarin (4b);31 1-(3-methoxyphenyl)-2-propanone
(7);18a 1-(1,3-benzodioxol-5-yl)-2-propanone (8);32 1-(2,5-Di-
methoxyphenyl)-2-propanone (9);33 2-(4-Fluorophenyl)-1-phen-
ylethanone (10);34 3-(4-Fluorophenyl)-2-butanone (11);35 2-[3-
(Trifluoromethyl)phenyl]-1-phenylethanone (12);34 3-[3-(Tri-
fluoromethyl)phenyl]-2-butanone (13);20 3-(4-cyanophenyl)-2-
butanone (15);36 2-(4-methoxyphenyl)-1-phenylethanone (16);37
3-(4-methoxyphenyl)-2-butanone (17);35 3-(3-pyridyl)-2-bu-
tanone (18);38 Benzeneacetic acid, R-methyl-methyl ester
(20);39 Benzeneacetic acid, 4-fluoro-R-methyl-methyl ester
Ack n ow led gm en t. We gratefully acknowledge the
CNRS (UMR 28) for financial support, and the Minis-
te`re de l’Enseignement Supe´rieur et de la Recherche for
a fellowship to M.D.
Registr y Nu m ber s (p r ovid ed by th e a u th or ). (1), 103-
79-7; (2), 459-03-0; (3), 21906-39-8; (4a ), 7115-18-6; (4b),
25539-21-7; (5), 22744-50-9; (6), 122-89-9; (7), 3027-13-2; (8),
4676-39-5; (9), 14293-24-4; (10), 347-91-1; (11), 79341-86-9;
(12), 30934-66-8; (13), 21906-07-0; (15), 79341-85-8; (16),
24845-40-7; (17), 7074-12-6; (18), 66702-67-8; (19), 101-41-7;
(20), 31508-44-8; (21), 34837-84-8; (22), 50415-71-9; (23) (-),
145983-12-6; (24), 125670-61-3; (25), 52798-01-3; (26), 125670-
62-4; (27), 6767-29-9; (28), 79443-97-3; (29), 50415-73-1; (30),
72221-62-6; (31), 30012-51-2; (32), 29891-75-5; (33), 94041-
87-9; (34), 1813-96-3; (35), 1813-97-4; (36), 140-67-0; (37a ),
18322-84-4; (37b), 18272-83-8; (39), 587-79-1; (40), 13132-15-
5; (41), 103-25-3; (42) (E), 588879-30-4; (42) (Z), 154309-36-
1; (43), 140675-27-0; (43) (E), 74254-13-0; (44), 4180-23-8.
J O9518314
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