Efficient allylation of active ketones promoted by p-nitrobenzoic acid

Article abstract of DOI:10.1002/cjoc.201090210

A general and practical method of allylation of carbonyl compounds promoted by p-nitrobenzoic acid under mild reaction condition has been developed. p-Nitrobenzoic acid can be easily recovered after workup by aqueous HCl.

Full text of DOI:10.1002/cjoc.201090210

FULL PAPER
Efficient Allylation of Active Ketones Promoted by
Xie, Zhengfenga,c(解正p峰-)Nitrobenzoic Acid
Li, Guilongb(李桂龙)
Zhao, Gang*,b(赵刚)
Wang, Jide*,a,c(王吉德)
a School of Sciences, Xi'an Jiaotong University, Xi'an, Shaanxi 710049, China
b Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy
of Sciences, Shanghai 200032, China
c College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi, Xinjiang 830046, China
A general and practical method of allylation of carbonyl compounds promoted by p-nitrobenzoic acid under
mild reaction condition has been developed. p-Nitrobenzoic acid can be easily recovered after workup by aqueous
HCl.
Keywords allylic compounds, α-keton esters, trifluoro-phenylethanones, allylation, allyltributyltin, p-nitrobenzoic
acid
Introduction
tion of aldehydes due to its appropriate acidity and
solubility in acetonitrile. Therefore, we initially used
p-nitrobenzoic acid as a promoter to investigate the al-
lylation of α-keton esters. As shown in the Table 1,
when 1.0 equiv. of p-nitrobenzoic acid was used as a
promoter, the allylation of ethyl benzoylformate (1a)
could provide the corresponding homoallylic alcohol 3a
in 61% yield after 22 h at room temperature. The yields
were increasing along with the increase of the amount
of promoter and tin reagent. Excellent yield (93%, Table
1, Entry 3) was obtained when excess of p-nitrobenzoic
acid and tributylallyltin was used.
The allylation of carbonyl compounds, using allyltin
reagents, as a very important method to synthesize syn-
thetically useful homoallylic alcohols, has been a sub-
ject of extensive investigation during the past years.
Generally, this type of allylation with allyltin reagents
should be carried out in the presence of Lewis acids or
other catalysts.1,2 Recently, we have found that carbox-
ylic acids are efficient promoters for the allylation of
aldehydes and imines under mild reaction conditions.3
But under the same reaction conditions, it is difficult for
the carboxylic acids to promote the allylation of ketones
(Scheme 1).3a α-Keton esters and other active ketones
are important intermediates in organic synthesis.4 In
order to extend the scope of the allylation mediated by
carboxylic acids, herein, we would like to report an ef-
ficient allylation of some active ketones with tributylal-
lyltin by using p-nitrobenzoic acid as a promoter.
Table 1 The optimization of reaction conditions of allylation of
active ketones
Entry
1a/2/p-nitrobenzoic acid
1.0/1.1/1.0 (equiv.)
1.0/1.2/1.0 (equiv.)
1.0/1.4/1.4 (equiv.)
Time/h Yielda/%
Scheme 1
1
2
3
22
49
48
61
80
93b
(1)
a Determined by 1H NMR. b Isolated yield.
(2)
The scope of the p-nitrobenzoic acid-mediated ally-
lation of active ketones was evaluated. The results are
summarized in Table 2. It is clearly that the allylation of
most aromatic α-keton esters could proceed smoothly
and afforded moderate to excellent yields. For examples,
if the aromatic ring of α-keton ester was substituted with
Results and discussion
In the former studies, we have found that
p-nitrobenzoic acid is the best promoter for the allyla-
*
E-mail: awangjd@xju.edu.cn; zhaog@mail.sioc.ac.cn; Tel./ Fax: 0086-0991-8582807
Received October 14, 2009; revised March 31, 2010; accepted April 6, 2010.
Project supported by the National Natural Science Foundation of China (Nos. 20962018, 20862015, 20762009, 20562011).
1212
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 1212— 1216

Efficient Allylation of Active Ketones Promoted by p-Nitrobenzoic Acids
electron-withdrawing groups, the allylations resulted in
high yields of the corresponding homoallylic alcohols
(Table 2, Entries 4 and 5). The low yield provided by
α-keton ester 1b may be due to the steric hindrance of
the 2-methyl group. In addition, only trace amount of
allylation products was detected when aromatic α-keton
ester, which was substituted with strong electron-do-
nating group, such as methoxyl, was used as a substrate
(Table 2, Entry 7). The allylation of aliphatic α-keton
ester also gave only trace amount product even after 48
h (Table 2, Entry 10). Finally, another kind of active
ketone, trifluoromethyl ketone, was examined. As
shown in Table 2, the allylation of various trifluoro-
methyl ketones promoted by p-nitrobenzoic acid pro-
vided very high yields of the desired products (Table 2,
Entries 11— 14).
At this time, the exact process of the allylation of ac-
tive ketone compounds promoted by p-nitrobenzoic acid
is not very clear. Based on the results of our experi-
ments,3b a possible mechanism is proposed. The active
ketone compounds (1) were activated by p-nitrobenzoic
acid through hydrogen bonding, the resulting electro-
phile intermediate I could attack 2 on C1 (adjoining tin
atom) involving a six-centered cyclic transition state II,
the products 3 are obtained.
α-keton esters and trifluoromethyl ketones promoted by
p-nitrobenzoic acid proceeded smoothly under mild re-
action conditions and gave the corresponding homoally-
lic alcohols in good to excellent yields. A possible
mechanism for the allylation was discussed.
Experimental
General information
All solvents were distilled prior to use except where
noted. Reactions were monitored by thin-layer chroma-
tography (TLC) carried out on 0.25 mm silica gel plates
visualized with UV light and/or by staining with I2.
Flash column chromatography was performed on silica
gel H (10— 40 mesh). NMR spectra were recorded on
Varian Mercury 300 and/or Unity 400 MHz instruments.
Chemical shifts (δ) are relative to TMS. IR spectra were
recorded on a Nicolet 320 Avatar FT-IR spectrometer.
Mass spectra (MS) were measured with an HP-5989A
spectrometer. High resolution mass spectra (HRMS)
were recorded on a Finnigan MAT-95 mass spectrome-
ter.
Typical procedure for the allylation of carbonyl
compounds
In summary, we have successfully extended the car-
boxylic acids-mediated allylation to active ketones.
After extensively studies, we found that the allylation of
To a suspension of p-nitrobenzoic acid (46.8 mg,
0.28 mmol) in acetonitrile (0.5 mL) were added
Scheme 2 Proposed mechanism for the allylation promoted by p-nitrobenzoic acid
Table 2 The scope of the allylation of active ketones mediated by p-nitrobenzoic acid
Entry
1
Active ketone
Product
Yield/%
93
Ref.
5a
O
CO2Me
HO
OMe
O
3a
CO2Et
1a
O
HO
OEt
OEt
2
68
—
—
O
CH3
3b
CH3
1b
O
CO2Et
HO
3
90
O
CH3
CH3
3c
1c
Chin. J. Chem. 2010, 28, 1212— 1216
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1213

Xie et al.
FULL PAPER
Continued
Ref.
Entry
4
Active ketone
Product
Yield/%
96
O
CO2Et
HO
OEt
—
O
F3C
F3C
3d
CO2Et
1d
O
HO
HO
OEt
OEt
5
6
7
8
95
92
—
—
—
—
O
O
Cl
Br
Cl
Br
3e
1e
O
CO2Et
3f
1f
O
CO2Et
HO
OEt
trace
83
O
O
MeO
MeO
3g
1g
CO2Et
HO
OEt
O
MeO
MeO
3h
1h
O
CO2Pr-i
HO
O
9
92
trace
97
—
O
3i
1i
O
HO
CO2Pr-i
O
10
11
12
—
3j
O
1j
O
HO CF3
CF3
5d
3k
1k
O
O
HO CF3
CF3
CF3
CF3
99
—
—
—
Cl
Br
F
Cl
Br
F
3l
1l
HO CF3
13
14
95
89
3m
1m
O
HO CF3
3n
1n
successively carbonyl compound (1a) (32.8 mg, 0.2
mmol) and allyltributyltin (92.7 mg, 0.28 mmol) at
room temperature. After being stirred for 48 h, the reac-
tion was quenched with NaOH (1 mol/L, 2 mL), then
extracted with CH2Cl2 (5 mL× 3). The combined or-
ganic layer was dried over Na2SO4 and concentrated
under reduced pressure to furnish the crude product,
which was purified by silica gel chromatography (typi-
cal eluent: petroleum ether/EtOAc, V∶ V＝ 14∶ 1) to
afford product 3a (38 mg, 93%). The aqueous layer was
acidified with 1 mol/L HCl. The white precipitate was
filtered and washed with ice water to afford the
p-nitrobenzoic acid.
Methyl 2-hydroxy-2-phenylpent-4-enoate (3a)4a
1
Colorless oil . H NMR (CDCl3, 300 MHz) δ: 2.73—
3.01 (m, 2H), 3.71 (s, 1H), 3.77 (s, 3H), 5.11— 5.20 (m,
2H), 5.72— 5.83 (m, 1H), 7.29— 7.38 (m, 2H), 7.58—
7.61 (m, 2H); IR (KBr, film) ν: 3512, 3076, 2954, 2924,
1736, 1641, 1494, 1448, 1438, 1232, 1145, 1071, 922,
－
1
733 cm .
1214
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© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 1212— 1216

Efficient Allylation of Active Ketones Promoted by p-Nitrobenzoic Acids
Ethyl
2-hydroxy-2-o-tolylpent-4-enoate
(3b)
2981, 2936, 1728, 1641, 1589, 1486, 1396, 1279, 1228,
1
－1
Colorless oil. H NMR (CDCl3, 300 MHz) δ: 1.18—
1.25 (m, 3H), 2.35 (s, 3H), 2.98—3.03 (m, 2H), 3.62 (s,
1H), 4.11—4.29 (m, 2H), 5.18—5.23 (m, 2H), 5.80—
5.89 (m, 1H), 7.13—7.24 (m, 3H), 7.45—7.48 (m, 1H);
13C NMR (CDCl3, 75 MHz) δ: 14.01, 20.65, 43.13,
62.18, 77.92, 119.60, 125.62, 126.25, 128.06, 132.16,
132.24, 137.31, 138.67, 175.17; IR (KBr, film) ν: 3512,
3077, 2980, 2936, 1728, 1641, 1459, 1263, 1227, 1178,
1146, 1076, 1＋010, 921, 828 cm ; HRMS calcd for
C13H15O3BrNa 321.0112, found 321.0096.
Ethyl 2-hydroxy-2-(6-methoxynaphthalen-2-yl)-
1
pent-4-enoate (3h) Colorless oil. H NMR (CDCl3,
300 MHz) δ: 1.24 (t, J＝6.9 Hz, 3H), 2.83 (dd, J＝6.5,
6.7 Hz, 1H), 3.03 (dd, J＝7.7, 6.2 Hz, 1H), 3.90 (s, 3H),
4.14—4.33 (m, 2H), 5.13—5.23 (m, 2H), 5.78—5.91
(m, 1H), 7.12—7.25 (m, 2H), 7.66—7.76 (m, 3H), 8.02
(s, 1H); 13C NMR (CDCl3, 75 MHz) δ: 14.17, 44.10,
55.35, 62.54, 78.01, 105.44, 119.07, 119.36, 124.21,
124.49, 126.68, 128.53, 129.90, 132.48, 134.02, 136.55,
158.01, 174.73; IR (KBr, film) ν: 3501, 3075, 2980,
2937, 2907, 2840, 1727, 1634, 16－05, 1484, 1390, 1267,
－1
1139, 1080, 1033, 920, 742 cm ; LRMS (ESI) m/z:
257.1 [M ＋ Na ＋ ]; HRMS calcd for C14H18O3Na
257.1148, found 257.1148.
Ethyl 2-hydroxy-2-m-tolylpent-4-enoate (3c)
1
Colorless oil. H NMR (CDCl3, 300 MHz) δ: 1.06 (t,
1
J＝7.1 Hz, 3H), 2.28 (s, 3H), 2.63 (dd, J＝1.5, 5.5 Hz,
1H), 2.85 (dd, J＝7.7, 6.4 Hz, 1H), 3.66 (s, 1H), 4.07—
4.21 (m, 2H), 5.03—5.13 (m, 2H), 5.66—5.79 (m, 1H),
7.00 (d, J＝7.5 Hz, 2H), 7.13—7.18 (m, 1H), 7.29 (m,
J＝7.9, 6.8 Hz, 2H); 13C NMR (CDCl3, 75 MHz) δ:
14.07, 21.54, 44.13, 62.34, 77.93, 119.11, 122.61,
126.14, 128.11, 128.50, 132.52, 137.86, 141.49, 174.62;
IR (KBr, film) ν: 3512, 3076, 2981, 2924, 1726, 1641,
1221, 1169, 1092＋, 1032, 854 cm ; LRMS (ESI) m/z:
318.0 (M ＋ NH4 ); HRMS calcd for C18H20O4Na
323.1267, found 323.1253.
Isopropyl 2-hydroxy-2-phenylpent-4-enoate (3i)
1
Colorless oil. H NMR (CDCl3, 300 MHz) δ: 1.18 (d,
J＝5.8 Hz, 3H), 1.25 (d, J＝6.7 Hz, 3H), 2.70 (dd, J＝
6.4, 5.7 Hz, 1H), 2.91 (dd, J＝6.8, 6.5 Hz, 1H), 3.81 (s,
1H), 5.00—5.20 (m, 3H), 5.74—5.85 (m, 1H), 7.25—
7.37 (m, 3H), 7.59—7.63 (m, 2H); 13C NMR (CDCl3,
75 MHz) δ: 21.49, 21.71, 44.16, 70.43, 77.75, 119.08,
125.51, 127.67, 128.16, 132.44, 141.69, 174.13; IR
(KBr, film) ν: 3511, 3076, 2982, 2934, 1724, 1641,
1449, 1376, 1266, 1232, 1105, 1070, 916, 733, 698
－1
1606, 1223, 1085, 1036, 920, 698 cm ; LRMS (ESI)
m/z: 252.1 (M＋ NH＋4 ); HRMS calcd for C14H18O3Na
257.1148, found 257.1148.
Ethyl 2-hydroxy-2-(4-(trifluoromethyl)phenyl)-
1
pent-4-enoate (3d) Colorless oil. H NMR (CDCl3,
－1
300 MHz) δ: 1.26 (t, J＝7.1 Hz, 3H), 2.71 (dd, J＝6.4,
7.7 Hz, 1H), 2.93 (dd, J＝7.6, 6.5 Hz, 1H), 3.88 (s, 1H),
4.17—4.32 (m, 2H), 5.13—5.20 (m, 2H), 5.73—5.79
(m, 1H), 7.60 (d, J＝8.4 Hz, 2H), 7.75 (d, J＝8.5 Hz,
2H); 13C NMR (CDCl3, 75 MHz) δ: 14.03, 44.39, 62.83,
77.79, 119.68, 125.08, 125.12, 125.18, 125.22, 126.17,
131.76, 145.32, 145.34, 173.93; IR (KBr, film) ν: 3507,
3081, 2984, 2939, 1729, 1642, 1618, 1412, 1328, 1265,
cm ; LRMS (ESI) m/z: 252.2 (M＋ NH＋4 ); HRMS
calcd for C14H18O3Na＋ 257.1159, found 257.1148.
1,1,1-Trifluoro-2-phenylpent-4-en-2-ol
(3k)4d
1
Colorless oil. H NMR (CDCl3, 300 MHz) δ: 2.65 (s,
1H), 2.80—2.88 (m, 1H), 2.94—3.02 (m, 1H), 5.18—
5.27 (m, 2H), 5.51—5.57 (m, 1H), 7.34—7.43 (m, 3H),
7.55—7.58 (m, 2H); 19F NMR (CDCl3, 300 MHz) δ:
－79.16 (s, CF3); IR (KBr, film) ν: 3551, 3067, 3033,
2984, 2929, 1643, 1498, 1450, 1271, 1163, 1073, 996,
－1
1231, 1167, 1127, 1070, 1018, 846 cm ; LRMS (ESI)
m/z: 311.2 (M＋Na＋); HRMS calcd for C15H15F O＋3
929, 767, 714 cm .
－1
3
289.1043, found 289.1046
2-(4-Chlorophenyl)-1,1,1-trifluorpent-4-en-2-ol
(3l) Colorless oil. 1H NMR (CDCl3, 300 MHz) δ: 2.70
(s, 1H), 2.78—2.97 (m, 2H), 5.20—5.27 (m, 2H), 5.46
—5.61 (m, 1H), 7.34—7.38 (m, 2H), 7.49—7.52 (m,
2H); 19F NMR (CDCl3, 300 MHz) δ: －79.28 (s, CF3);
13C NMR (CDCl3, 75 MHz) δ: 40.24, 75.78 (sCH1, qCF,
2JCF＝28.2 Hz, COH), 122.21, 125.13 (sCH, qCF, JCF＝
283.8 Hz, CF3), 128.03, 128.55, 129.96, 134.72, 135.41;
IR (KBr, film) ν: 3545, 3083, 2927, 1643, 1599, 1495,
Ethyl 2-(4-chlorophenyl)-2-hydroxypent-4-enoate
(3e) Colorless oil. 1H NMR (CDCl3, 300 MHz) δ: 1.24
(t, J＝7.4 Hz, 3H), 2.68 (dd, J＝6.8, 7.5 Hz, 1H), 2.88
(dd, J＝7.8, 6.2 Hz, 1H), 3.80 (s, 1H), 4.15—4.30 (m,
2H), 5.12—5.19 (m, 2H), 5.72—5.83 (m, 1H), 7.29—
7.33 (m, 2H), 7.53—7.56 (m, 2H); 13C NMR (CDCl3,
75 MHz) δ: 14.06, 29.68, 44.27, 62.63, 77.59, 119.46,
127.16, 128.34, 132.00, 133.79, 139.98, 174.22; IR
(KBr, film) ν: 3510, 3078, 2982, 2926, 2854, 1727,
1641, 1491, 1228, 1189, 1146, 1093, 1014, 921, 831
－1
1269, 1231, 1164, 1097, 1014, 942, 824, 735 cm ;
LRMS (EI) m/z: 211, 209, 141, 139, 111, 77, 69, 51, 41.
Anal. calcd for C11H10ClF3O: C 52.71, H 4.02; found C
52.66, H 4.08.
－1
cm ; LRMS (ESI) m/z: 272.1 (M＋ NH＋4 ); HRMS
calcd for C13H15O3Na＋ 277.0605, found 277.0601.
Ethyl 2-(4-bromophenyl)-2-hydroxypent-4-enoate
(3f) Colorless oil. 1H NMR (CDCl3, 300 MHz) δ: 1.26
(t, J＝7.7 Hz, 3H), 2.70 (dd, J＝6.5, 7.7 Hz, 1H), 2.90
(dd, J＝7.2, 6.9 Hz, 1H), 3.84 (s, 1H), 4.17—4.31 (m,
2H), 5.14—5.21 (m, 2H), 5.72—5.86 (m, 1H), 7.47—
7.53 (m, 4H); 13C NMR (CDCl3, 75 MHz) δ: 14.13,
44.24, 62.76, 77.62, 119.62, 122.00, 127.53, 131.34,
131.98, 140.45, 174.20; IR (KBr, film) ν: 3504, 3078,
2-(4-Bromophenyl)-1,1,1-trifluorpent-4-en-2-ol
1
(3m) Colorless oil. H NMR (CDCl3, 300 MHz) δ:
2.68 (s, 1H), 2.78—2.97 (m, 2H), 5.21—5.27 (m, 2H),
5.47—5.61 (m, 1H), 7.42—7.46 (m, 2H), 7.51—7.56
(m, 2 H); 19F NMR (CDCl3, 300 MHz) δ: －79.25 (s,
CF3); 13C NMR (CDCl3, 75 MHz) δ: 40.22, 75.65 (sCH
,
,
qCF, 2JCF＝28.2 Hz, COH), 122.30, 122.97, 125.04 (sCH
1
qCF, JCF＝283.8 Hz, CF3), 128.33, 129.93, 131.53,
Chin. J. Chem. 2010, 28, 1212— 1216
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1215

Xie et al.
FULL PAPER
135.95; IR (KBr, film) ν: 3544, 3083, 2923, 2850, 1643,
Organometallics 2005, 24, 2617.
1593, 1491,－1399, 1269, 1231, 1163, 1076, 1010, 942,
155, 77, 69, 51, 41; LRMS (ESI) m/z: 318 [M＋Na ],
279, 277. Anal. calcd for C11H10BrF3O: C 44.77, H 3.42;
found C 44.85, H, 3.39.
(q) Teo, Y.-C.; Tan, K.-T.; Loh, T.-P. Chem. Commun.
2005, 1318.
(r) Lu, J.; Hong, M.-L.; Ji, S.-J.; Loh, T.-P. Chem. Commun.
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(s) Kwiatkowski, P.; Jurczak, J. Synlett 2005, 227.
(t) Krishnaveni, N. S.; Surendra, K.; Kumar, V. P.; Srinivas,
B.; Reddy, C. S.; Rao, K. R. Tetrahedron Lett. 2005, 46,
4299.
(a) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem.
Soc. 2003, 125, 1708.
(b) Hanawa, H.; Uraguchi, D.; Konishi, S.; Hashimoto, T.;
Maruoka, K. Chem. Eur. J. 2003, 9, 4405.
(c) Xia, G.-Y.; Shibatomi, K.; Yamamoto, H. Synlett 2004,
2437.
(d) Choudary, B. M.; Jyothi, K.; Madhi, S.; Kantam, M. L.
Synlett 2004, 231.
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S. Tetrahedron 2005, 61, 879.
(f) Kulkarni, N. A.; Chen, K. Tetrahedron Lett. 2006, 47,
611.
1
820, 734 cm ; LRMS (EI) m/z: 255, 253, 185, 183, 1＋57,
1,1,1-Trifluoro-2-(4-fluorophenyl)pent-4-en-2-ol
(3n) 1H NMR (CDCl3, 300 MHz) δ: 2.66 (s, 1H), 2.79
—2.94 (m, 2H), 5.22—5.28 (m, 2H), 5.50—5.57 (m,
1H), 7.05—7.11 (m, 2H), 7.52—7.57 (m, 2H); 19F NMR
(CDCl3, 300 MHz) δ: －79.44 (s, CF3), －113.71 (s);
13C NMR (CDCl3, 75 MHz) δ: 40.35, 75.56 (sCH, qCF,
2
2
2JCF＝28.2 Hz, COH), 115.27 (dCF, JCF＝21.4 Hz),
122.18, 125.04 (qCF, 1JCF＝283.8 Hz, CF3), 128.48 (dCF,
4
3JCF＝8.2 Hz), 130.11, 132.65 (dCF, JCF＝3.1 Hz),
1
162.84 (dCF, JCF＝245.9 Hz); IR (KBr, film) ν: 3565,
2919, 2849, 1606, 151－3, 1271, 1237, 1163, 1093, 1015,
1
996, 940, 834, 738 cm ; LRMS (EI) m/z: 193, 123, 95,
69, 57, 41. Anal. calcd for C11H10F4O: C 56.41, H 4.30;
found C 56.46, H 4.25.
(g) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D.
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Tetrahedron Lett. 2002, 43, 323.
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