Nickel-catalyzed intermolecular insertion of aryl iodides to nitriles: A novel method to synthesize arylketones

Article abstract of DOI:10.1021/ol300153f

A novel procedure for the NiCl₂(DME)/dppp/Zn system catalyzed intermolecular insertion of aryl iodides to nitriles was developed, which afforded variously substituted arylketone derivatives in moderate to good yields with tolerance of a wide variety of functional groups.

Full text of DOI:10.1021/ol300153f

Supplementary Information
Nickel-Catalyzed Intermolecular Insertion of Aryl Iodides to
Nitriles: A Novel Method to Synthesize Arylketones
Jen-Chieh Hsieh*, Yen-Chung Chen, An-Yi Cheng and Hsiao-Chun Tseng
Department of Chemistry, Tamkang University, New Taipei City, 25137, Taiwan (R.O.C.)
jchsieh@mail.tku.edu.tw
Table of Contents
I. General Information and procedure
Page S2
Page S2–S16
Page S17
II. Experimental Details for all compounds
Ⅲ
Ⅳ
. References
1
13
. H and C NMR spectra
Page S18–S60
S1

General information: All reagents were purchased from Sigma-Aldrich, Fisher-
Acros, TCI, or Alfa-Aesar, and were used without further purification unless
2 3
otherwise noted. THF and Et O were distilled from sodium, and CH CN was distilled from
CaH . All manipulations of oxygen- and moisture-sensitive materials were conducted
2
with a standard Schlenk technique. Flash column chromatography was performed
using silica gel (230-400 mesh). Analytical thin layer chromatography (TLC) was
performed on 60 F254 (0.25 mm) plates and visualization was accomplished with UV
light (254 and 354 nm) and/or an aqueous alkaline KMnO
4
solution followed by
1
13
heating. Proton and carbon nuclear magnetic resonance spectra ( H NMR and C
NMR) were recorded on a Bruck 600 spectrometer with Me
4
Si or solvent resonance
1
13
as the internal standard ( H NMR, Me
4
Si at 0 ppm, CHCl
3
at 7.26 ppm; C NMR,
1
Me
4
Si at 0 ppm, CDCl
3
at 77.0 ppm). H NMR data are reported as follows: chemical
shift, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, quint = quintet, sext
sextet, sept = septet, br = broad, m = multiplet), coupling constants (Hz), and
=
integration. IR spectral data were recorded on a Brucker TENSOR 37 spectrometer.
Melting points (mp) were determined using a Fargo MP-1D. High Resolution Mass
spectral data were obtained from the MAT-95XL HRMS by using EI method.
General procedure for the intermolecular insertion of iodoarenes with nitriles:
To a screw-capped vial (4-mL) were added NiBr
2
(DME) (0.1 mmol, 16 mg), dppp
(
0.1 mmol, 21 mg) zinc powder (1.0 mmol, 65 mg) in DME (1,2-dimethoxyethane,
0
.3 mL). The vial was sealed with septum and allowed to stir at r.t. for a while; the
O (1.2 mmol) were then injected
aryl iodides (0.5 mmol), nitriles (1.0 mmol) and H
2
into the reaction mixture via a syringe. The septum was removed, and the vial was
sealed with a screw cap. The reaction mixture was stirred at 100 °C for 36 h. The
2 2
crude reaction mixture was diluted with CH Cl , filtered through a thin Celite pad,
and concentrated in vacuo. The residue was isolated through a column
chromatography by using hexane and ethyl acetate as eluent to give the pure product.
Products 3 were obtained according to this procedure. The known structures were
1
13
characterized by the HRMS and the H NMR and C NMR spectra of reported
1
-11
1
literatures. Spectral data, melting point, HRMS data and the copies of H NMR and
1
3
C NMR spectra for all compounds are listed below.
S2

1
1
1
2
7
1
1
,2-Diphenylethanone (3aa): White solid, mp: 53–55 °C; IR (KBr): 2966, 2964,
-1 1
658, 1632, 1469, 750, 690 cm ; H NMR (600 MHz, CDCl
3
): δ 8.02 (d, J = 7.2 Hz,
H), 7.56 (t, J = 7.2 Hz, 1 H), 7.46 (t, J = 7.8 Hz, 2 H), 7.33 (t, J = 7.8 Hz, 2 H),
13
.24–7.28 (m, 3 H), 4.29 (s, 2 H); C NMR (150 MHz, CDCl
3
): δ 197.6, 136.6, 134.5,
33.1, 129.5, 128.7, 128.6, 126.9, 45.5; HRMS: C14
96.0885; Registry Number: [451-40-1].
H12O calculated 196.0888, found
2
2
-(4-Chlorophenyl)-1-phenylethanone (3ab): White solid, mp: 129–130 °C; IR
-1
(
KBr): 3059, 2938, 2912, 1684, 1448, 1412, 1334, 1104, 868, 753, 689, 571, 500 cm ;
1
H NMR (600 MHz, CDCl
3
): δ 8.00 (dd, J
1
= 8.4 Hz, J
2
= 1.2 Hz, 2 H), 7.58 (t, J = 7.2
= 1.8 Hz, 2 H), 7.20 (dd,
= 1.8 Hz, 2 H), 4.26 (s, 2 H); C NMR (150 MHz, CDCl ): δ 197.1,
36.4, 133.4, 133.0, 132.9, 130.9, 128.8, 128.7, 128.5, 44.7; HRMS: C14
Hz, 1 H), 7.47 (t, J = 7.8 Hz, 2 H), 7.30 (dd, J
1
= 6.6 Hz, J
2
1
3
J
1
= 6.6 Hz, J
2
3
1
H11ClO
calculated 230.0498, found 230.0499; Registry Number: [6332-83-8].
3
2
-(4-Fluorophenyl)-1-phenylethanone (3ac): White solid, mp: 125–127 °C; IR
(
KBr): 2919, 2850, 1683, 1653, 1559, 1541, 1508, 1449, 1420, 1336, 1093, 867, 847,
-1 1
8
30, 797, 753, 690, 652, 571, 523, 420 cm ; H NMR (600 MHz, CDCl ): δ 8.01 (d, J
3
=
7.8 Hz, 2 H), 7.58 (t, J = 7.8 Hz, 1 H), 7.47 (t, J = 7.8 Hz, 2 H), 7.23 (dd, J
1
= 7.8
= 5.4 Hz, 2 H), 4.27 (s, 2 H); C NMR
): δ 197.4, 161.9 (d, J = 244.5 Hz), 136.5, 133.3, 131.0 (d, J = 7.5
Hz), 130.1, 128.7, 128.5, 115.5 (d, J = 21 Hz), 44.5; HRMS: C14 11FO calculated
13
2 1 2
Hz, J = 5.4 Hz, 2 H), 7.02 (dd, J = 7.8 Hz, J
(150 MHz, CDCl
3
H
2
14.0794, found 214.0799; Registry Number: [347-91-1].
S3

3
2
-([1,1'-Biphenyl]-4-yl)-1-phenylethanone (3ad): White solid, mp: 146–148 °C; IR
-1 1
(
KBr): 2922, 2851, 1655, 1561, 1384, 1117, 751, 688, 484 cm ; H NMR (600 MHz,
CDCl ): δ 8.05 (dd, J = 7.8 Hz, J = 1.2 Hz, 2 H), 7.56–7.59 (m, 5 H), 7.48 (t, J = 7.8
Hz, 2 H), 7.43 (t, J = 7.8 Hz, 2 H), 7.32–7.35 (m, 3 H), 4.34 (s, 2 H); C NMR (150
MHz, CDCl ): δ 197.6, 140.8, 139.9, 136.6, 133.5, 133.2, 129.9, 128.7, 128.7, 128.6,
27.4, 127.2, 127.0, 45.1; HRMS: C20
Registry Number: [27644-00-4].
3
1
2
1
3
3
1
H
16O calculated 272.1201, found 272.1206;
3
2
-(4-Methoxyphenyl)-1-phenylethanone (3ae): White solid, mp: 106–107 °C; IR
(
KBr): 3056, 2954, 2835, 1742, 1692, 1586, 1516, 1446, 1411, 1335, 1246, 1183,
-1 1
1
107, 1035, 862, 823, 793, 756, 691, 656, 570, 521 cm ; H NMR (600 MHz, CDCl
3
):
δ 8.02 (dt, J
1
= 8.4 Hz, J
= 1.8 Hz, 2 H), 7.20 (dt, J
= 2.4 Hz, 2 H), 4.23 (s, 2 H), 3.78 (s, 3 H); C NMR (150 MHz, CDCl
2
= 1.8 Hz, 2 H), 7.56 (td, J
1
= 7.8 Hz, J
2
= 1.8 Hz, 1 H), 7.46
(
td, J
1
= 7.8 Hz, J
2
1
= 8.4 Hz, J
2
= 1.8 Hz, 2 H), 6.88 (dt, J
1
1
3
=
9.6 Hz, J
2
3
):
δ 197.8, 158.5, 136.6, 133.0, 130.4, 128.5, 128.5, 126.4, 114.1, 55.2, 44.5; HRMS:
C
15
H
14
O
2
calculated 226.0994, found 226.0999; Registry Number: [24845-40-7].
3
2
-(Benzo[d][1,3]dioxol-5-yl)-1-phenylethanone (3af): Yellow solid, mp: 65–67 °C;
IR (KBr): 2921, 2852, 1677, 1638, 1490, 1446, 1384, 1248, 1190, 1101, 1039, 927,
-
1 1
6
2
6
2
1
2
92, 591, 498 cm ; H NMR (600 MHz, CDCl
H), 7.56 (td, J = 7.8 Hz, J = 1.8 Hz, 1 H), 7.46 (dt, J
.76 (d, J = 8.4 Hz, 2 H), 6.71 (dd, J = 7.8 Hz, J = 1.8 Hz, 1 H), 5.92 (s, 2 H), 4.20 (s,
): δ 197.6, 147.8, 146.5, 136.5, 133.1, 128.6, 128.5,
3
): δ 8.00 (dd, J
1
= 7.8 Hz, J
2
= 1.2 Hz,
1
2
1
= 7.8 Hz, J
2
= 1.8 Hz, 2 H),
1
2
1
3
H); C NMR (150 MHz, CDCl
3
28.0, 122.5, 109.9, 108.4, 101.0, 45.0; HRMS: C15
40.0789; Registry Number: [40804-81-7].
12 3
H O calculated 240.0786, found
S4

1
2
6
7
-Phenyl-2-(3,4,5-trimethoxyphenyl)ethanone (3ag): Colorless oil; IR (KBr): 2925,
842, 1685, 1655, 1637, 1591, 1508, 1458, 1422, 1385, 1324, 1241, 1211, 1125, 1006,
-1 1
91, 597 cm ; H NMR (600 MHz, CDCl
3 1 2
): δ 8.02 (dd, J = 7.8 Hz, J = 1.2 Hz, 2 H),
.57 (t, J = 7.2 Hz, 1 H), 7.47 (t, J = 7.8 Hz, 2 H), 6.48 (s, 2 H), 4.22 (s, 2 H), 3.83 (d,
1
3
J = 4.8 Hz, 9 H); C NMR (150 MHz, CDCl
30.0, 128.7, 128.6, 106.6, 60.8, 56.1, 45.7; HRMS: C17
found 286.1199; New compound.
3
): δ 197.6, 153.3, 137.0, 136.6, 133.2,
1
18 4
H O
calculated 286.1205,
4
2
-(2-Chlorophenyl)-1-phenylethanone (3ah): Yellow solid, mp: 75–77 °C; IR
(
KBr): 3058, 2908, 1692, 1595, 1579, 1475, 1448, 1406, 1333, 1220, 1201, 1179,
-1 1
1
161, 1075, 1050, 993, 953, 909, 764, 753, 688, 657, 568, 446 cm ; H NMR (600
3
MHz, CDCl ): δ 8.04 (d, J = 7.8 Hz, 2 H) 7.58 (t, J = 7.8 Hz, 1 H), 7.48 (t, J = 7.8 Hz,
13
2
H), 7.40–7.42 (m, 1 H), 7.22–7.25 (m, 3 H), 4.44 (s, 2 H); C NMR (150 MHz,
CDCl
3
): δ 196.3, 136.6, 134.4, 133.3, 133.1, 131.6, 129.5, 128.7, 128.5, 128.3, 126.9,
11ClO calculated 230.0498, found 230.0494; Registry Number:
4
3.2; HRMS: C14
H
[57479-60-4].
2
-(Benzo[d][1,3]dioxol-5-yl)-1-(p-tolyl)ethanone (3bf): Yellow solid, mp: 89–91 °C;
IR (KBr): 3026, 2093, 2780, 1685, 1604, 1505, 1448, 1406, 1385, 1358, 1327, 1258,
1
4
8
221, 1194, 1102, 1037, 987, 926, 871, 812, 778, 755, 691, 631, 605, 579, 563, 524,
-1 1
67, 423 cm ; H NMR (600 MHz, CDCl
3
): δ 7.91 (d, J = 8.4 Hz, 2 H), 7.25 (d, J =
= 8.4 Hz, J = 1.8
): δ
97.1, 147.7, 146.4, 143.8, 133.9, 129.2, 128.5, 128.2, 122.4, 109.8, 108.2, 100.8,
.4 Hz, 2 H), 6.75 (dd, J = 7.8 Hz, J = 1.8 Hz, 2 H), 6.71 (dd, J
1
2
1
2
1
3
Hz, 1 H), 5.90 (s, 2 H), 4.16 (s, 2 H), 2.40 (s, 3 H); C NMR (150 MHz, CDCl
3
1
4
4.9, 21.5; HRMS: C16
H
14
O
3
calculated 254.0943, found 254.0936; New compound.
S5

2
-(Benzo[d][1,3]dioxol-5-yl)-1-(4-methoxyphenyl)ethanone (3cf): Pale yellow solid,
mp: 103–104 °C; IR (KBr): 2900, 2840, 1671, 1600, 1575, 1504, 1490, 1444, 1419,
375, 1313, 1251, 1219, 1171, 1119, 1037, 992, 928, 830, 805, 785, 605, 566, 419
1
-1 1
cm ; H NMR (600 MHz, CDCl
8.4 Hz, 2 H) 6.74 (dd, J = 7.8 Hz, J
Hz, 1 H), 5.90 (s, 2 H), 4.13 (s, 2 H), 3.85 (s, 3 H); C NMR (150 MHz, CDCl
3
) δ 7.98 (dd, J
1
= 7.2 Hz, J
2
= 1.8 Hz, 2 H) 6.92 (d, J
= 7.8 Hz, J = 1.2
): δ
96.2, 163.5, 147.7, 146.4, 130.8, 129.5, 128.4, 122.4, 113.7, 109.8, 108.3, 100.9,
5.4, 44.7; HRMS: C16 calculated 270.0892, found 270.0897; New compound.
=
1
2
= 2.4 Hz, 2 H), 6.70 (dd, J
1
2
1
3
3
1
5
14 4
H O
2
7
1
-(Benzo[d][1,3]dioxol-5-yl)-1-(4-chlorophenyl)ethanone (3df): Yellow solid, mp:
2–74 °C; IR (KBr): 2896, 1686, 1589, 1490, 1444, 1399, 1306, 1248, 1190, 1092,
-
1 1
3
039, 992, 928, 815, 767, 521 cm ; H NMR (600 MHz, CDCl ): δ 7.93 (d, J = 8.4
Hz, 2 H), 7.42 (d, J = 8.4 Hz, 2 H), 6.76 (d, J = 7.8 Hz, 1 H), 6.73 (s, 1 H), 6.69 (d, J
1
3
=
7.8 Hz, 1 H), 5.93 (s, 2 H), 4.15 (s, 2 H); C NMR (150 MHz, CDCl
47.9, 146.4, 139.6, 134.7, 130.0, 128.9, 127.6, 122.5, 109.7, 108.5, 101.0, 45.1;
calculated 274.0397, found 274.0395; New compound.
3
): δ 196.4,
1
HRMS: C15H11ClO
3
1
-(4-Acetylphenyl)-2-(4-chlorophenyl)ethanone (3eb): Yellow solid, mp: 128–130
-1 1
°
C; IR (KBr): 1682, 1404, 1332, 1307, 1267, 1096, 831, 597, 509 cm ; H NMR (600
MHz, CDCl ): δ 8.06 (d, J = 8.4 Hz, 2 H), 8.03 (d, J = 8.4 Hz, 2 H), 7.31 (d, J = 8.4
Hz, 2 H), 7.19 (d, J = 8.4 Hz, 2 H), 4.28 (s, 2 H), 2.64 (s, 3 H); C NMR (150 MHz,
CDCl ): δ 197.3, 196.5, 140.3, 139.5, 133.1, 132.3, 130.8, 128.9, 128.7, 128.6, 45.0,
6.9; HRMS: C16
3
1
3
3
2
H13ClO
2
calculated 272.0604, found 272.0595; New compound.
S6

2
2
7
7
5
1
1
-(Benzo[d][1,3]dioxol-5-yl)-1-(m-tolyl)ethanone (3ff): Brown oil; IR (KBr): 2898,
778, 1742, 1679, 1603, 1585, 1490, 1444, 1328, 1248, 1187, 1157, 1100, 1039, 928,
-
1
1
86, 736, 691, 614 cm ; H NMR (600 MHz, CDCl
3
): δ 7.79–7.81 (m, 2 H),
= 7.8 Hz, J = 1.8 Hz, 1 H),
.93 (s, 2 H), 4.18 (s, 2 H), 2.41 (s, 3 H); C NMR (150 MHz, CDCl ): δ 197.9,
47.8, 146.5, 138.5, 136.6, 133.9, 129.0, 128.5, 128.2, 125.8, 122.5, 109.9, 108.4,
01.0, 45.1, 21.4; HRMS: C16 calculated 254.0943, found 254.0944; New
.33–7.38 (m, 2 H), 6.76 (d, J = 7.8 Hz, 2 H), 6.71 (dd, J
1
2
13
3
14 3
H O
compound.
O
O
O
2
-(Benzo[d][1,3]dioxol-5-yl)-1-(3,5-dimethylphenyl)ethanone (3gf): Brown oil; IR
(
KBr): 2927, 2855, 1655, 1638, 1629, 1561, 1509, 1384, 1093, 670, 592, 504, 484,
-1
1
4
38, 428, 409 cm ; H NMR (600 MHz, CDCl
.75–6.77 (m, 2 H), 6.70 (dd, J = 8.4 Hz, J = 1.2 Hz, 1 H), 5.92 (s, 2 H), 4.17 (s, 2
): δ 198.0, 147.7, 146.4, 138.2, 136.6,
34.8, 128.2, 126.5, 126.3, 126.3, 122.5, 109.9, 108.3, 100.9, 45.0, 21.2 (2 C); HRMS:
calculated 268.1099, found 268.1100; New compound.
3
): δ 7.61 (s, 2 H), 7.20 (s, 1 H),
6
1
2
1
3
H), 2.37 (s, 6 H); C NMR (150 MHz, CDCl
3
1
17 16 3
C H O
2
-(Benzo[d][1,3]dioxol-5-yl)-1-(3,4-dimethoxyphenyl)ethanone (3hf): Yellow solid,
mp: 87–89 °C; IR (KBr): 2962, 2935, 2839, 1672, 1587, 1515, 1490, 1444, 1417,
-
1
1
1
384, 1268, 1247, 1151, 1130, 1036, 1023, 928, 872, 811, 785, 626, 588 cm ; H
NMR (600 MHz, CDCl ): δ 7.64 (dd, J = 8.4 Hz, J = 1.8 Hz, 1 H), 7.55 (d, J = 1.8
Hz, 1 H), 6.88 (d, J = 8.4 Hz, 1 H), 6.75–6.76 (m, 2 H), 6.71–6.73 (m, 1 H), 5.92 (s, 2
3
1
2
1
3
H), 4.15 (s, 2 H), 3.94 (s, 3 H), 3.92 (s, 3 H); C NMR (150 MHz, CDCl
3
): δ 196.3,
53.4, 149.1, 147.8, 146.5, 129.7, 128.6, 123.4, 122.4, 110.7, 110.0, 109.8, 108.4,
01.0, 56.1, 56.0, 44.8; HRMS: C17 calculated 300.0998, found 300.0987; New
1
1
16 5
H O
compound.
S7

2
-(Benzo[d][1,3]dioxol-5-yl)-1-(2-fluorophenyl)ethanone (3if): Brown oil; IR
(
KBr): 3079, 2899, 2779, 1686, 1609, 1577, 1504, 1491, 1450, 1332, 1269, 1249,
-1
1
1
212, 1189, 1152, 1100, 1039, 995, 929, 822, 788, 764, 606, 538, 513, 495, 421 cm ;
H NMR (600 MHz, CDCl
3
): δ 7.84 (td, J
= 7.8 Hz, J = 1.8 Hz, 1 H), 7.13 (dd, J
.74 (t, J = 1.8 Hz, 2 H), 6.69 (dd, J = 7.8 Hz, J = 1.8 Hz, 1 H), 5.93 (s, 2 H), 4.20 (d,
): δ 196.2 (d, J = 3.0 Hz), 161.7 (d, J =
52 Hz), 147.7, 146.6, 134.6 (d, J = 9.0 Hz), 131.0, 127.5, 125.5 (d, J = 13.5 Hz),
24.5 (d, J = 3.0 Hz), 122.8, 116.6 (d, J = 24.0 Hz), 110.1, 108.3, 100.9, 49.5 (d, J =
.5 Hz); HRMS: C15 calculated 258.0692, found 258.0696; New compound.
1
= 7.8 Hz, J
2
= 1.8 Hz, 1 H), 7.50–7.52 (m,
1
6
H), 7.21 (td, J
1
2
1
= 7.8 Hz, J = 1.8 Hz, 1 H),
2
1
2
1
3
J = 2.4 Hz, 2 H); C NMR (150 MHz, CDCl
3
2
1
7
H11FO
3
2
1
7
7
-(Naphthalen-1-yl)-1-(o-tolyl)ethanone (3ji): Yellow oil; IR (KBr): 2927, 1678,
-1 1
598, 1562, 1482, 1384, 784 cm ; H NMR (600 MHz, CDCl
.83 (dd, J = 7.8 Hz, J = 1.2 Hz, 1 H), 7.79 (d, J = 8.4 Hz, 1 H), 7.47–7.51 (m, 2 H),
.42 (t, J = 7.8 Hz, 1 H), 7.38 (td, J = 7.2 Hz, J = 1.8 Hz, 1 H), 7.35 (d, J = 6.6 Hz, 1
3
): δ 7.86–7.89 (m, 2 H),
1
2
1
2
1
3
H), 7.28 (t, J = 7.8 Hz, 1 H), 7.24 (d, J = 7.2 Hz, 1 H), 4.67 (s, 2 H), 2.42 (s, 3 H); C
NMR (150 MHz, CDCl ): δ 201.5, 138.6, 137.6, 133.9, 132.3, 132.1, 131.4, 131.3,
28.8, 128.5, 128.3, 127.9, 126.3, 125.7, 125.6, 125.5, 123.9, 46.2, 21.2; HRMS:
16O calculated 260.1201, found 260.1206; New compound.
3
1
19
C H
2
3
1
-(4-Chlorophenyl)-1-(2-methoxyphenyl)ethanone (3kb): Yellow oil; IR (KBr):
073, 2967, 2943, 2839, 1676, 1598, 1486, 1465, 1436, 1331, 1283, 1246, 1163, 1092,
-
1 1
017, 993, 804, 756, 628, 495 cm ; H NMR (600 MHz, CDCl
= 1.8 Hz, 1 H), 7.47 (td, J = 7.8 Hz, J = 1.8 Hz, 1 H), 7.27 (d, J = 8.4 Hz, 2
H), 7.16 (d, J = 8.4 Hz, 2 H), 7.00 (td, J = 7.8 Hz, J = 1.2 Hz, 1 H), 6.97 (d, J = 8.4
Hz, 1 H), 4.27 (s, 2 H), 3.92 (s, 3 H); C NMR (150 MHz, CDCl ): δ 199.4, 158.4,
33.7, 133.7, 132.4, 131.0, 130.6, 128.4, 127.8, 120.7, 111.5, 55.4, 49.4; HRMS:
3 1
): δ 7.68 (dd, J = 7.8
Hz, J
2
1
2
1
2
1
3
3
1
S8

C
15
2
H13ClO calculated 260.0604, found 260.0595; New compound.
O
O
1
3
7
1
7
-(2-(Methoxymethyl)phenyl)-2-phenylethanone (3la): Yellow oil; IR (KBr): 3064,
030, 2925, 2822, 1685, 1601, 1573, 1496, 1453, 1375, 1320, 1262, 1195, 1100, 970,
-1 1
58, 730, 698, 667, 594, 476 cm ; H NMR (600 MHz, CDCl
3
): δ 7.78 (d, J = 7.8 Hz,
H), 7.67 (d, J = 7.2 Hz, 1 H), 7.51 (t, J = 7.8 Hz, 1 H), 7.34–7.38 (m, 3 H),
1
3
.27–7.30 (m, 3 H), 4.74 (s, 2 H), 4.25 (s, 2 H), 3.40 (s, 3 H); C NMR (150 MHz,
): δ 201.0, 139.4, 136.2, 134.2, 131.5, 129.5, 128.5, 128.4, 127.7, 126.8, 126.7,
2.4, 58.4, 47.8; HRMS: C16 calculated 240.1150, found 240.1145; New
compound.
CDCl
3
7
16 2
H O
2
-(Benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxyphenyl)ethanone (3’f): Yellow oil; IR
(
KBr): 3459, 2899, 1638, 1612, 1579, 1489, 1445, 1357, 1339, 1308, 1245, 1188,
-1 1
1
156, 1038, 993, 928, 789, 754, 715, 622 cm ; H NMR (600 MHz, CDCl
s, 1 H), 7.84 (dd, J = 7.8 Hz, J = 1.2 Hz, 1 H), 7.47 (td, J = 8.4 Hz, J = 1.2 Hz, 1
H), 6.99 (d, J = 8.4 Hz, 1 H), 6.91 (td, J = 7.8 Hz, J = 1.2 Hz, 1 H), 6.79 (d, J = 8.4
Hz, 1 H), 6.76 (d, J = 1.8 Hz, 1 H), 6.72 (dd, J = 7.8 Hz, J = 1.8 Hz, 1 H), 5.95 (s, 2
): δ 203.9, 162.9, 148.0, 146.8, 136.6,
30.3, 127.4, 127.4, 122.6, 119.0, 118.7, 109.8, 108.5, 101.1, 44.7; HRMS: C15
calculated 256.0736, found 256.0738; New compound.
3
): δ 12.20
(
1
2
1
2
1
2
1
2
1
3
H), 4.21 (s, 2 H); C NMR (150 MHz, CDCl
3
1
12 4
H O
2
-(Benzo[d][1,3]dioxol-5-yl)-1-(naphthalen-1-yl)ethanone (3nf): Brown oil; IR
(
KBr): 2920, 2852, 1684, 1489, 1443, 1385, 1246, 1172, 1090, 1038, 927, 773, 739,
-1 1
6
13, 483 cm ; H NMR (600 MHz, CDCl
.4 Hz, 1 H), 7.93 (dd, J = 7.2 Hz, J = 1.2 Hz, 1 H), 7.86 (d, J = 7.8 Hz, 1 H), 7.57
= 8.4 Hz, J = 1.2 Hz, 1 H), 7.53 (td, J = 8.4 Hz, J = 1.2 Hz, 1 H), 7.49 (t, J =
3
): δ 8.58 (d, J = 8.4 Hz, 1 H), 7.98 (d, J =
8
1
2
(
td, J
1
2
1
2
1
7.8 Hz, 1 H), 6.81 (d, J = 1.2 Hz, 1 H), 6.76 (d, J = 7.8 Hz, 1 H), 6.74 (dd, J = 8.4 Hz,
S9

1
3
J
2
= 1.2 Hz, 1 H), 5.92 (s, 2 H), 4.28 (s, 2 H); C NMR (150 MHz, CDCl
3
): δ 201.5,
1
1
2
47.8, 146.5, 135.4, 133.9, 132.7, 130.4, 128.3, 127.9, 127.8, 126.4, 125.8, 124.2,
22.6, 109.9, 108.9, 108.4, 100.9, 48.4; HRMS: C19
90.0938; New compound.
14 3
H O calculated 290.0943, found
Cl
O
2
-(4-Chlorophenyl)-1-(naphthalen-1-yl)ethanone (3nb): Brown solid, mp: 105–106
°
C; IR (KBr): 2922, 2852, 1679, 1595, 1505, 1399, 1318, 1174, 1092, 1014, 970, 946,
-1 1
9
27, 906, 863, 838, 807, 789, 773, 756, 669, 646, 618, 562, 516, 498, 447 cm ; H
): δ 8.58 (d, J = 8.4 Hz, 1 H), 8.00 (d, J = 8.4 Hz, 1 H), 7.94
d, J = 7.2 Hz, 1 H), 7.88 (d, J = 8.4 Hz, 1 H), 7.58 (td, J = 7.2 Hz, J = 1.8 Hz, 1 H),
.54 (t, J = 7.2 Hz, 1 H), 7.50 (t, J = 7.8 Hz, 1 H), 7.30 (dd, J = 8.4 Hz, J = 1.8 Hz, 2
): δ 200.9,
35.2, 134.0, 133.0, 132.9, 130.9, 130.3, 128.8, 128.4, 128.1, 127.9, 126.6, 125.7,
24.2, 48.0; HRMS (ESI): C18 13ClO calculated 280.0655, found 280.0649; New
NMR (600 MHz, CDCl
3
(
1
2
7
1
2
1
3
H), 7.23 (d, J = 8.4 Hz, 2 H), 4.34 (s, 2 H); C NMR (150 MHz, CDCl
3
1
1
H
compound.
5
-1 1
Acetophenone (3aj): Colorless oil; IR (KBr): 2922, 2852, 1629, 1385, 1113 cm ; H
NMR (600 MHz, CDCl ): δ 7.96 (d, J = 7.2 Hz, 2 H), 7.56 (t, J = 7.2 Hz, 1 H), 7.46 (t,
J = 7.8 Hz, 2 H), 2.61 (s, 3 H); C NMR (150 MHz, CDCl
28.6, 128.3, 26.6; HRMS: C O calculated 120.0575, found 120.0577; Registry
3
1
3
3
): δ 198.1, 137.2, 133.1,
1
8 8
H
Number: [98-86-2].
O
1
1
-Phenylbutan-1-one (3ak): Colorless oil; IR (KBr): 2923, 2853, 1648, 1559, 1541,
-1 1
1
508, 1449, 1385, 1111, 804, 738, 443 cm ; H NMR (600 MHz, CDCl
= 8.4 Hz, J = 1.2 Hz, 2 H), 7.52–7.54 (m, 1 H), 7.44 (t, J = 7.2 Hz, 2 H), 2.93 (t, J
7.2 Hz, 2 H), 1.76 (sext, J = 7.2 Hz, 2 H), 1.00 (t, J = 7.2 Hz, 3 H); C NMR (150
): δ 200.3, 137.1, 132.8, 128.5, 127.9, 40.4, 17.7, 13.8; HRMS: C10
3
): δ 7.95 (dd,
J
1
2
1
3
=
MHz, CDCl
3
12
H O
calculated 148.0888, found 148.0883; Registry Number: [495-40-9].
S10

6
1
-Phenylheptan-1-one (3am): Colorless oil; IR (KBr): 2959, 2928, 2856, 1686,
-1 1
1
638, 1384, 1103, 733, 696, 592, 506 cm ; H NMR (600 MHz, CDCl
3
): δ 7.96 (d, J
=
2
7.8 Hz, 2 H), 7.55 (t, J = 7.2 Hz, 1 H), 7.46 (t, J = 7.8 Hz, 2 H), 2.96 (t, J = 7.2 Hz,
1
3
H), 1.74 (quint, J = 7.2 Hz, 2 H), 1.26–1.42 (m, 6 H), 0.88–0.90 (m, 3 H); C NMR
(150 MHz, CDCl
3
): δ 200.6, 137.1, 132.8, 128.5, 128.1, 38.6, 31.7, 29.1, 24.4, 22.5,
1
4.0; HRMS: C13
H18O calculated 190.1358, found 190.1354; Registry Number:
[1671-75-6].
O
7
1
3
5
,4-Diphenylbutan-1-one (3an): White solid, mp: 59–61 °C; IR (KBr): 3085, 3061,
026, 2924, 2854, 1685, 1598, 1496, 1449, 1368, 1264, 1226, 1120, 1001, 743, 691,
-1 1
3
62, 488 cm ; H NMR (600 MHz, CDCl ): δ 7.93 (d, J = 7.2, 2 H), 7.55 (t, J = 7.8, 1
H), 7.45 (t, J = 7.8 Hz, 2 H), 7.30 (t, J = 7.2 Hz, 2 H), 7.20–7.23 (m, 3 H), 2.99 (t, J =
1
3
7
.2 Hz, 2 H), 2.74 (t, J =7.8 Hz, 2 H), 2.10 (quint, J = 7.8 Hz, 2 H); C NMR (150
MHz, CDCl ): δ 200.1, 141.7, 137.0, 132.9, 128.5, 128.5, 128.4, 128.0, 125.9, 37.7,
5.2, 25.7; HRMS: C16 16O calculated 224.1201, found 224.1204; Registry Number:
5407-91-0].
3
3
H
[
6
-Oxo-6-phenylhexanenitrile (3ao): Pale yellow solid, mp: 68–70 °C; IR (KBr):
-1
2
958, 2872, 2248, 1676, 1541, 1458, 1385, 1111, 1075, 755, 729, 692, 569, 419 cm ;
1
H NMR (600 MHz, CDCl
3
): δ 7.94 (d, J = 7.2 Hz, 2 H), 7.56 (t, J = 7.8 Hz , 1 H),
7
.46 (t, J = 7.8 Hz, 2 H), 3.03 (t, J = 7.2 Hz, 2 H), 2.39 (t, J = 7.2 Hz, 2 H), 1.87–1.92
1
3
(
m, 2 H), 1.73–1.78 (m, 2 H); C NMR (150 MHz, CDCl
28.6, 127.9, 119.4, 37.3, 24.9, 23.0, 17.1; HRMS: C12 13NO calculated 187.0997,
found 187.0994; New compound.
3
): δ 199.0, 136.6, 133.1,
1
H
1
2
-Methyl-1-phenylpropan-1-one (3ap): Colorless oil; IR (KBr): 2922, 2851, 1655,
-1 1
1
3
638, 1560, 1499, 1459, 1385, 1114, 744, 479 cm ; H NMR (600 MHz, CDCl ): δ
S11

7
.94 (d, J = 7.8 Hz, 2 H), 7.53 (t, J = 7.8 Hz, 1 H), 7.45 (t, J = 7.8 Hz, 2 H), 3.53–3.57
1
3
(
m, 1 H), 1.21 (d, J = 7.2 Hz, 6 H); C NMR (150 MHz, CDCl
3
): δ 204.4, 136.2,
1
1
32.7, 128.5, 128.2, 35.3, 19.1; HRMS: C10
48.0886; Registry Number: [611-70-1].
H12O calculated 148.0888, found
1
Cyclohexyl(phenyl)methanone (3aq): White solid, mp: 60–62 °C; IR (KBr): 3061,
-
1 1
2
932, 2854, 1681, 1597, 1448, 1373, 1252, 1207, 974, 765, 698 cm ; H NMR (600
MHz, CDCl ): δ 7.94 (dd, J = 7.8 Hz, J = 1.8 Hz, 2 H), 7.54 (tt, J = 7.8 Hz, J = 1.8
Hz, 1 H), 7.45 (td, J = 7.2 Hz, J = 1.8 Hz, 2 H), 3.26 (tt, J = 11.4 Hz, J = 3.6 Hz, 1
H), 1.83–1.91 (m, 4 H), 1.72–1.76 (m, 1 H), 1.47–1.53 (m, 2 H), 1.36–1.43 (m, 2 H),
3
1
2
1
2
1
2
1
2
1
3
1
4
.24–1.31 (m, 1 H); C NMR (150 MHz, CDCl
3
): δ 203.9, 136.4, 132.7, 128.6, 128.2,
5.6, 29.4, 26.0, 25.9; HRMS: C13
H
16O calculated 188.1201, found 188.1204;
Registry Number: [712-50-5].
O
O
8
1
-(4-Methoxyphenyl)ethanone (3cj): Colorless oil; IR (KBr): 2923, 2842, 1675,
-1 1
1
3
601, 1510, 1358, 1258, 1172, 1028, 957, 835, 564 cm ; H NMR (600 MHz, CDCl ):
13
δ 7.92 (d, J = 9.0 Hz, 2 H), 6.92 (d, J = 9.0 Hz, 2 H), 3.85 (s, 3 H), 2.54 (s. 3 H); C
NMR (150 MHz, CDCl ): δ 196.7, 163.4, 130.5, 130.3, 113.6, 55.4, 26.3; HRMS:
3
C
9
H
10
O
2
calculated 150.0681, found 150.0677; Registry Number: [100-06-1].
9
1
2
8
,1'-(1,4-Phenylene)diethanone (3ej): Yellow solid, mp: 120–121 °C; IR (KBr):
-1 1
922, 2852, 1677, 1384, 1312, 1119, 835, 604 cm ; H NMR (600 MHz, CDCl
3
): δ
1
3
.03 (s, 4 H), 2.65 (s, 6 H); C NMR (150 MHz, CDCl
3
): δ 197.5, 140.2, 128.5, 26.9;
HRMS: C10
H
10
O
2
calculated 162.0681, found 162.0684; Registry Number:
[1009-61-6].
S12

O
4
1
8
2
-Phenyl-1-(p-tolyl)butan-1-one (3bn): Colorless oil; IR (KBr): 2925, 1679, 1655,
-1 1
3
638, 1384, 815, 700, 590, 502, 435 cm ; H NMR (600 MHz, CDCl ): δ 7.83 (d, J =
.4 Hz, 2 H), 7.29 (t, J = 7.8 Hz, 2 H), 7.25 (t, J = 6.6 Hz, 2 H), 7.19–7.22 (m, 3 H),
.96 (t, J = 7.2 Hz, 2 H), 2.72 (t, J = 7.2 Hz, 2 H), 2.41 (s, 3 H), 2.08 (quint, J = 7.8
1
3
Hz, 2 H); C NMR (150 MHz, CDCl
3
): δ 199.8, 143.7, 141.7, 134.5, 129.2, 128.5,
18O calculated 238.1358,
1
28.4, 128.1, 125.9, 37.6, 35.2, 25.8, 21.6; HRMS: C17
H
found 238.1361; New compound.
O
1
-(3,5-Dimethylphenyl)butan-1-one (3gk): Yellow oil; IR (KBr): 2964, 2931, 1685,
-1 1
1
637, 1607, 1560, 1458, 1383, 1316, 1183, 1055, 847, 789, 687 cm ; H NMR (600
MHz, CDCl
3
): δ 7.56 (s, 2 H), 7.19 (s, 1 H), 2.92 (t, J = 7.2 Hz, 2 H), 2.37 (s, 6 H),
1
3
1
2
1
.76 (sext, J = 7.2 Hz, 2 H), 1.00 (t, J = 7.2 Hz, 3 H); C NMR (150 MHz, CDCl
3
): δ
00.9, 138.1, 137.3, 134.5, 125.8, 40.6, 21.2, 17.9, 13.9; HRMS: C12
76.1201, found 176.1199; New compound.
H16O calculated
1
-(2-Methoxyphenyl)pentan-1-one (3kl): Yellow oil; IR (KBr): 2961, 2934, 2873,
-1
1
1
677, 1599, 1486, 1466, 1438, 1384, 1287, 1246, 1163, 1026, 757 cm ; H NMR
): δ 7.64 (dd, J = 7.2 Hz, J = 1.8 Hz, 1 H), 7.44 (td, J = 7.2 Hz, J
1.8 Hz, 1 H), 6.99 (td, J = 7.2 Hz, J = 1.8 Hz, 1 H), 6.95 (d, J = 8.4 Hz, 1 H), 3.89
(600 MHz, CDCl
3
1
2
1
2
=
1
2
(
s, 3 H), 2.96 (t, J = 7.8 Hz, 2 H), 1.66 (quint, J = 7.8 Hz, 2 H), 1.37 (sext, J = 7.8 Hz,
1
3
2
1
1
H), 0.93 (t, J = 7.8 Hz, 3 H); C NMR (150 MHz, CDCl
3
): δ 203.3, 158.3, 133.0,
calculated
30.1, 129.1, 120.7, 111.6, 55.5, 43.5, 26.6, 22.5, 13.9; HRMS: C12
92.1150, found 192.1147; New compound.
16 2
H O
S13

1
-(Naphthalen-1-yl)-4-phenylbutan-1-one (3nn): Colorless oil; IR (KBr): 2962,
-1 1
2
3
926, 2854, 1638, 1384, 700, 663, 594, 505 cm ; H NMR (600 MHz, CDCl ): δ 8.55
(
d, J = 8.4 Hz, 1 H), 7.97 (d, J = 7.8 Hz, 1 H), 7.88 (d, J = 7.8 Hz, 1 H), 7.79 (d, J =
7
1
=
.2 Hz, 1 H), 7.58 (td, J
1
= 7.2 Hz, J
2 1 2
= 1.2 Hz, 1 H), 7.53 (td, J = 7.2 Hz, J = 1.2 Hz,
H), 7.48 (t, J = 7.2 Hz, 1 H), 7.29 (t, J = 7.8 Hz, 2 H), 7.19–7.22 (m, 3 H), 3.07 (t, J
1
3
7.2 Hz, 2 H), 2.76 (t, J = 7.8 Hz, 2 H), 2.15 (quint, J = 7.8 Hz, 2 H); C NMR (150
): δ 204.6, 141.6, 136.3, 134.0, 132.4, 130.1, 128.5, 128.4, 127.8, 127.2,
26.4, 126.0, 125.7, 124.3, 41.4, 35.2, 26.1; HRMS: C20 18O calculated 274.1358,
MHz, CDCl
3
1
H
found 274.1357; New compound.
O
1
0
Benzophenone (3ar): White solid, mp: 48–50 °C; IR (KBr): 2924, 2853, 1656,
-
1 1
1
447, 1431, 1384, 1277, 1114, 941, 919, 809, 763, 699, 638 cm ; H NMR (600 MHz,
CDCl ): δ 7.79 (d, J = 7.2 Hz, 4 H), 7.56 (t, J = 7.8 Hz, 2 H), 7.46 (t, J = 7.8 Hz, 4 H);
C NMR (150 MHz, CDCl ): δ 196.5, 137.4, 132.2, 129.8, 128.1; HRMS: C13
calculated 182.0732, found 182.0734; Registry Number: [119-61-9].
3
1
3
3
10
H O
(
2-(Methoxymethyl)phenyl)(phenyl)methanone (3lr): Colorless oil; IR (KBr):,
3
9
7
7
1
064, 2985, 2926, 2891, 2824, 1666, 1598, 1448, 1384, 1315, 1271, 1195, 1154, 1094,
-1 1
27, 766, 736, 701, 641 cm ; H NMR (600 MHz, CDCl ): δ 7.80 (d, J = 7.2 Hz, 2 H),
3
.55–7.59 (m, 2 H), 7.50 (td, J
.34–7.38 (m, 2 H), 4.54 (s, 2 H), 3.25 (s, 3 H); C NMR (150 MHz, CDCl
38.0, 137.7, 133.0, 130.4, 130.0, 128.8, 128.3, 128.3 (3 C), 126.9, 72.1, 58.3; HRMS:
1 2
= 7.8 Hz, J = 1.8 Hz, 1 H), 7.45 (t, J = 7.8 Hz, 2 H),
1
3
3
): δ 197.8,
C
15
H
14
O
2
calculated 226.0994, found 226.0996; New compound.
S14

O
O
F
(
4-Fluorophenyl)(2-(methoxymethyl)phenyl)methanone (3ls): Yellow oil; IR
(
KBr): 3070, 2986, 2927, 2824, 1666, 1598, 1504, 1448, 1149, 1094, 1013, 957, 929,
-1
1
853, 781, 749, 683, 632, 602, 573, 505 cm ; H NMR (600 MHz, CDCl
7.81–7.84 (m, 2 H), 7.54 (d, J =7.8 Hz, 1 H), 7.49 (td, J = 7.8 Hz, J = 2.4 Hz, 1 H),
7.33–7.37 (m, 2 H), 710–7.14 (m, 2 H), 4.52 (s, 2 H), 3.23 (s, 3 H); C NMR (150
): δ 196.3, 165.7 (d, J = 253 Hz), 137.8, 137.5, 134.0, 132.6 (d, J = 9.0
Hz), 130.5, 128.5 (d, J = 6.0 Hz), 127.0, 115.5 (d, J = 21.0 Hz), 115.0, 72.1, 58.4;
3
): δ
1
2
13
MHz, CDCl
3
2
HRMS: C15H13FO calculated 244.0900, found 244.0904; New compound.
O
F
11
(
4-Fluorophenyl)(o-tolyl)methanone (3js): Pale yellow oil; IR (KBr): 3069, 2927,
1
920, 1665, 1598, 1504, 1455, 1410, 1294, 1268, 1230, 1149, 927, 853, 793, 748, 606
-1 1
cm ; H NMR (600 MHz, CDCl
3
): δ 7.82–7.84 (m, 2 H), 7.39 (td, J
1 2
= 7.2 Hz, J =
1
2
1
1
.2 Hz, 1 H), 7.29 (d, J = 8.4 Hz, 2 H), 7.25 (t, J = 8.4 Hz, 1 H), 7.10–7.14 (m, 2 H),
1
3
.32 (s, 3 H); C NMR (150 MHz, CDCl
36.6, 134.1, 132.7 (d, J = 9.9 Hz), 131.0, 130.3, 128.2, 125.3, 115.6 (t, J = 22.5 Hz),
9.9; HRMS: C14 11FO calculated 214.0794, found 214.0802; Registry Number:
3
): δ 197.0, 165.8 (d, J = 253.5 Hz), 138.4,
H
[68295-42-1]
1
-(4-(2-Methylbenzoyl)phenyl)ethanone (3jt): Yellow solid, mp: 86–87 °C; IR
(
KBr): 3064, 2961, 2925, 1686, 1668, 1559, 1457, 1403, 1292, 1261, 959, 927, 856,
-1 1
782, 752, 729, 692, 664, 591, 419 cm ; H NMR (600 MHz, CDCl
7.8 Hz, 2 H), 7.86 (d, J = 8.4 Hz, 2 H), 7.42 (td, J = 7.8 Hz, J
7.30–7.32 (m, 2 H), 7.25–7.27 (m, 1 H), 2.65 (s, 3 H), 2.35 (s, 3 H); C NMR (150
): δ 197.8, 197.5, 141.2, 140.0, 137.8, 137.2, 131.2, 130.8, 130.2, 128.9,
28.3, 125.3, 26.9, 20.1; HRMS: C16 calculated 238.0994, found 238.0997;
New compound.
3
): δ 8.02 (d, J =
1
2
= 1.8 Hz, 1 H),
13
MHz, CDCl
3
1
14 2
H O
S15

(
2-Methoxyphenyl)(m-tolyl)methanone (3kv): Yellow oil; IR (KBr): 3025, 2923,
2
7
1
7
838, 1667, 1599, 1489, 1462, 1436, 1301, 1247, 1207, 1110, 1048, 1024, 958, 830,
-1 1
56, 723, 640 cm ; H NMR (600 MHz, CDCl
3
): δ 7.68 (s, 1 H), 7.58 (d, J = 7.2 Hz,
H), 7.44–7.46 (m, 1 H), 7.33–7.36 (m, 2 H), 7.29 (t, J = 7.8 Hz, 1 H), 7.03 (td, J
1
=
13
.8 Hz, J
2
= 1.2 Hz, 1 H), 6.99 (d, J = 8.4 Hz, 1 H), 3.70 (s, 3 H), 2.37 (s, 3 H); C
): δ 196.4, 157.1, 137.8, 137.6, 133.6, 131.6, 129.8, 129.2,
28.8, 127.9, 127.1, 120.2, 111.3, 55.4, 21.1; HRMS: C15 calculated 226.0994,
NMR (150 MHz, CDCl
3
1
14 2
H O
found 226.0991; New compound.
O
O
Cl
(
2-(Benzyloxy)phenyl)(4-chlorophenyl)methanone (3mu): Colorless oil; IR (KBr):
066, 3033, 2924, 2852, 1656, 1598, 1485, 1448, 1400, 1384, 1307, 1260, 1239, 1109,
3
1
6
7
2
1
-
1 1
090, 1014, 926, 844, 753, 696 cm ; H NMR (600 MHz, CDCl
.6 Hz, J = 1.8 Hz, 2 H), 7.44–7.48 (m, 2 H), 7.38 (dd, J = 6.6 Hz, J
.23–7.24 (m, 3 H), 7.08 (t, J = 7.8 Hz, 1 H), 7.03 (d, J = 8.4 Hz, 1 H), 6.98–7.00 (m,
3
): δ 7.73 (dd, J
1
=
2
1
2
= 1.8 Hz, 2 H),
1
3
H), 5.00 (s, 2 H); C NMR (150 MHz, CDCl
32.4, 131.0, 130.0, 128.9, 128.5, 128.3, 127.8, 126.7, 121.1, 112.8, 70.2; HRMS:
calculated 322.0761, found 322.0766; New compound.
3
): δ 195.5, 156.4, 139.1, 136.8, 136.2,
20 2
C H15ClO
1
2
1
-(2-Hydroxyphenyl)ethanone (3’j): Yellow oil; IR (KBr): 3051, 2923, 1642, 1488,
-1 1
1
448, 1368, 1303, 1245, 1221, 962, 754, 621, 522 cm ; H NMR (600 MHz, CDCl
= 7.8 Hz, J = 1.8 Hz, 1 H), 7.47 (td, J = 8.4 Hz, J = 1.8
Hz, 1 H), 6.98 (d, J = 7.8 Hz, 1 H), 6.90 (td, J = 7.8 Hz, J = 1.2 Hz, 1 H), 2.63 (s, 3
): δ 204.5, 162.4, 136.5, 130.7, 119.7, 118.9, 118.4,
3
):
δ 12.26 (s, 1 H), 7.73 (dd, J
1
2
1
2
1
2
1
3
H); C NMR (150 MHz, CDCl
3
2
6.6; HRMS: C
8
H
8
O
2
calculated 136.0524, found 136.0528; Registry Number:
[118-93-4].
S16

References
(
(
(
1) Wong, Y.-C.; Parthasarathy, K.; Cheng, C.-H. Org. Lett. 2010, 12, 1736.
2) Angle, S. R.; Neitzel, M. L. J. Org. Chem. 2000, 65, 6458.
3) Huang, K.; Li, G.; Huang, W.-P.; Yu, D.-G.; Shi, Z.-J. Chem. Commun. 2011, 47,
7
224.
(
(
(
(
(
(
4) Peng, Z.; Knochel, P. Org. Lett. 2011, 12, 3198.
5) Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321.
6) Lebel, H.; Ladjel, C. J. Org. Chem. 2005, 70, 10159.
7) Miao, T.; Wang, G.-W. Chem. Commun. 2011, 47, 9501.
8) Denmark, S. E.; Neuville, L. Org. Lett. 2000, 2, 3221.
9) Liu, S.; Berry, N.; Thomson, N.; Pettman, A.; Hyder, Z.; Mo, J.; Xiao, J. J. Org.
Chem. 2006, 71, 7467.
(
10) Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 14800.
11) Chen, J.-Y.; Chen, S.-C.; Tang, Y.-J.; Mou, C.-Y.; Tsai, F.-Y. J. Mol. Catal. A:
Chem. 2009, 307, 88.
(
(
12) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48,
8
725.
S17

1
13
H and C NMR Spectra (600 MHz, CDCl ) for all compounds
3
1
,2-Diphenylethanone (3aa)
S18

2
-(4-Chlorophenyl)-1-phenylethanone (3ab)
S19

2
-(4-fluorophenyl)-1-phenylethanone (3ac)
S20

2
-([1,1'-Biphenyl]-4-yl)-1-phenylethanone (3ad)
S21

2-(4-Methoxyphenyl)-1-phenylethanone (3ae)
S22

2
-(Benzo[d][1,3]dioxol-5-yl)-1-phenylethanone (3af)
S23

1
-Phenyl-2-(3,4,5-trimethoxyphenyl)ethanone (3ag)
S24

2
-(2-Chlorophenyl)-1-phenylethanone (3ah)
S25

2
-(Benzo[d][1,3]dioxol-5-yl)-1-(p-tolyl)ethanone (3bf)
S26

2
-(Benzo[d][1,3]dioxol-5-yl)-1-(4-methoxyphenyl)ethanone (3cf)
S27

2
-(Benzo[d][1,3]dioxol-5-yl)-1-(4-chlorophenyl)ethanone (3df)
S28

1
-(4-Acetylphenyl)-2-(4-chlorophenyl)ethanone (3eb)
S29

2
-(Benzo[d][1,3]dioxol-5-yl)-1-(m-tolyl)ethanone (3ff)
S30