Iodine(III)-mediated α-acetoxylation of aromatic ketones

Article abstract of DOI:10.3184/174751911X13081595869649

In the presence of iodobenzene diacetate with potassium iodide, aromatic α-phenoxy ketones underwent α-acetoxylation to afford corresponding α-acetoxy ketones smoothly at room temperature in moderate to good yields.

Full text of DOI:10.3184/174751911X13081595869649

346 RESEARCH PAPER
JUNE, 346–348
JOURNAL OF CHEMICAL RESEARCH 2011
Iodine(III)-mediated α-acetoxylation of aromatic ketones
Jiansheng Tanga,b*, Min Zhenga, Yao Chena and Cancheng Guob
aMathematics and Science Department, Hunan First Normal University, Changsha, 410205, P. R. China
bCollege of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China
In the presence of iodobenzene diacetate with potassium iodide, aromatic α-phenoxy ketones underwent
α-acetoxylation to afford corresponding α-acetoxy ketones smoothly at room temperature in moderate to good
yields.
Keywords: α-acetoxyaromatic ketones, iodobenzene diacetate, potassium iodide
α-Acetoxy aromatic ketones are versatile intermediates in
the synthesis of many biologically-active compounds.1,2 The
conventional synthetic methods for these compounds involve
the metal-induced α-acetoxylation of ketones such as
Mn(OAc)3,3–5 CF3SO3Tl(I)6 and Pb(OAc)4.7–8 However, these
methods require the use of hazardous chemicals. Hypervalent
iodine compounds have been used extensively in organic
synthesis as a result of their benign environmental character,
ready availability and versatility.9–24 An alternative approach
may involve iodine(III)-mediated α-acetoxylation reaction for
α-acetoxy ketones.21–24 For example, (1) the treatment of p-
substituted acetophenones with iodobenzene diacetate in acetic
acid / acetic anhydride in the presence of sulfuric acid,21–22 (2)
nosyloxylation of aromatic ketones and subsequent solvolysis
using acetic acid in the presence of silver carbonate,23 and (3)
tosyloxylation of ketones and subsequent solvolysis reaction
in DMA and addition of water.24 In these cases, the method is
limited to substrate specificity, low yields or a cumbersome
workup procedure. Recently an iodoxybenzene-catalysed
α-acetoxylation reaction has also been reported,25–27 the yield
is still undesirab-le. Thus, the development of a new iodine
(III)-mediated route to construct α-acetoxy aromatic ketones
efficiently and selectively is still significant. Herein we wish
to report a mild and general protocol for acetoxylation of
aromatic ketones by the combination of PhI(OAc)2 with KI
[Equation (1)].
and the results are summarised in Table 1. Initially, a series of
polyvalent iodine compounds combined with an iodine source
were investigated in CH3CN at room temperature in air. In the
absence of any iodine source, the reaction of ketone 1a with
PhI(OAc)2 did not occur (entry 1). Identical results were also
obtained using either I2 or NIS (entries 2 and 3). Gratifyingly,
the reaction of ketone 1a with PhI(OAc)2 and KI in CH3CN
gave the corresponding product 1-acetoxy-2-phenyl-1-(p-
tolyloxy)ethan-2-one (2a) in 83 % yield for 8 h (entry 4).
Changing the iodine source for NaI or Bu4NI did not improve
the results (entries 5 and 6). Subsequently, other solvents,
including THF, DCE, were investigated but were less effective
(entries 7 and 8). Finally, two other hypervalent iodine were
also investigated. With iodomesitylene diacetate instead of
PhI(OAc)2, the reaction was less effective but still gave a good
yield but no reaction was observed when the PhI(OAc)2 was
replaced by PhI(O2CCF3)2 (entries 9 and 10).
These results led us to explore the scope of the α-acetoxyl-
ation reaction under these optimal conditions (Table 2). Firstly,
a set of 1-aryl-2-phenoxyethanones 1b–e, being electron-rich
or electron-deficient substituents were treated with PhI(OAc)2
and KI reacted smoothly to give products in moderate to good
yields (entries 1–4). Gratifyingly, a good yield was still iso-
lated from naphthyl substrate (entry 5). The screening results
showed that several functional groups such as methoxy, iodo,
cholo, allyl groups on the aryl ring of 2-phenoxy-1-phenyleth-
anone moiety were perfectly tolerated (entries 6–10). A mod-
erate electronic substrate effect was observed. For example,
reaction of 1-phenyl-2-(p-tolyloxy)ethanone (1a) gave rise to
the corresponding product (2a) in 83% yield, while reaction of
2-(4-chlorophenoxy)-1-phe-nylethanone (1j) reacted in 37%
yield, respectively. In the presence of PhI(OAc)2 and KI, 1l and
1m were also compatible with the reaction conditions and
1-Phenyl-2-(p-tolyloxy)ethanone (1a) was chosen as the
starting substrate to identify the optimal reaction conditions,
Table 1 Screening optimal conditionsa
Entry
Polyvalent iodine /equiv.
I source /equiv.
Solvent
Time/h
Yield/%b
1
2
PhI(OAc)2 (2)
___
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
THF
24
24
24
8
0
0
PhI(OAc)2 (2)
I2 (3)
3
PhI(OAc)2 (2)
NIS (3)
KI (3)
NaI (3)
Bu4NI (3)
KI (3)
KI (3)
KI (3)
KI (3)
0
4
PhI(OAc)2 (2)
83
52
80
65
58
77
0
5
PhI(OAc)2 (2)
8
6
PhI(OAc)2 (2)
24
8
8
16
24
7
PhI(OAc)2 (2)
8
PhI(OAc)2 (2)
DCE
9
Iodomesitylene diacetate (2)
PhI(O2CCF3)2(2)
CH3CN
CH3CN
10
a Reaction conditions: substrate 1a (0.2 mmol), polyvalent iodine, I sourse and solvent (2 mL) at room temperature. b Isolated
yield.
* Correspondent. E-mail: yztjs@163.com

JOURNAL OF CHEMICAL RESEARCH 2011 347
Table 2 PhI(OAc)2-mediated α-acetoxylation of aromatic
A working mechanism as outlined in Scheme 1 is proposed
on the basis of the present results and the previously reported
mechanisms.15,23,28,29 Initially, an iodine(III) intermediate A is
generated by the interaction of PhI(OAc)2 with KI, and the
KOAc acts as a base to deprotonate ketones 1. The resulting
enolate anion of substrate B reacts with the iodine(III)
intermediate A via a ligand exchange reaction to yield an inter-
mediate C. Finally, intermediate C undergoes the reductive
elimination of PhI to the afford product 2.
ketonesa
Entry
Substrate 1
Yeild/%b
In summary, we have developed a mild and general protocol
for the acetoxylation of aromatic α-phenoxy ketones. In the
presence of PhI(OAc)2 and KI, a wide variety of α-acetoxy
α-phenoxy aromatic ketones obtained smoothly at room tem-
perature in air in moderate to good yields. Work to apply
the reaction in organic synthesis and develop more novel
acetoxylation processes is currently underway.
1
2
3
4
R1 = H (1b)
R1 = 4-Me (1c)
R1 = 4-MeO (1d)
R1 = 4-F (1e)
83(2b)
91(2c)
81(2d)
62(2e)
Experimental
NMR spectroscopy was performed on a Bruker-500 spectrometer
operating at 500 MHz (1H NMR) and 125 MHz (13C NMR). TMS
(tetramethylsilane) was used an internal standard and CDCl3 was
used as the solvent. Micro analyses were performed on a Perkin-
Elmer-2400 CHNS analyser in Changsha. Mass spectrometric analy-
sis was performed on Bruker APEX IV FTMS mass spectrometer
analysis. Melting points were determined on a digital melting-point
apparatus and were not corrected. Synthesis of substrates (1a–m,1o)
were accomplished via general routes from 2-bromo-1-arylethanone
5
77(2f)
6
7
8
9
R2 = 2-MeO (1g)
R2 = 3-MeO (1h)
R2 = 2-I (1i)
82(2g)
81(2h)
75(2i)
37(2j)
68(2k)
30
and arylphenol. Substrate (1n) was purchased from Aldrich and
used without further purification.
R2 = 4-Cl (1j)
10
R2 = 2-Allyl (1k)
Synthesis of α-acetoxy Aromatic Ketone (2); general procedure
The aromatic ketone 1 (0.2 mmol), PhI(OAc)2 (0.4 mmol), KI
(0.6 mmol) in CH3CN (2 mL) was stirred at room tempertature in air
for 8–12 h. and the reaction was monitored by TLC and GC-MS. The
reaction mixture was quenched with saturated Na2S2O3, and extracted
by ethyl ether (25 mL x 3). The organic layer was dried over anhy-
drous Na2SO4 and evaporated under vacuum. The residue was purified
by flash column chromatography on silica gel (hexane/ethyl acetate)
to afford the desired product 2.
11
12
13
14
78(2l)
76(2m)
80(2n)
trace
2-Oxo-2-phenyl-1-(p-tolyloxy)ethyl acetate (2a): Yellow oil; 1H
NMR (500 MHz, CDCl3) δ: 8.05 (d, J = 7.0 Hz, 2H), 7.62–7.59 (m,
1H), 7.47 (t, J = 7.5 Hz, 2H), 7.13 (d, J = 2.5 Hz, 1H), 7.11 (d, J =
3.5 Hz, 2H), 6.97 (d, J = 8.5 Hz, 2H), 2.31 (s, 3H), 2.19 (s, 3H);
13C NMR (125 MHz, CDCl3) δ: 189.4, 169.7, 153.5, 134.0, 133.2,
130.3, 129.4, 128.7, 116.6, 93.8, 20.8, 20.6; IR (KBr, cm−1): 1752,
1701; MS (EI): 284 (M+), 241, 105, 43. Anal. Calcd for C17H16O4:
C, 71.82; H, 5.67. Found: C, 71.80; H, 5.64%.
2-Oxo-1-phenoxy-2-phenylethyl acetate (2b): Yellow solid, m.p.
1
50.1–51.9 °C (uncorrected); H NMR (500 MHz, CDCl3) δ: 8.05 (d,
J = 7.5 Hz, 2H), 7.61 (t, J = 7.5 Hz, 1H), 7.48 (t, J = 8.0 Hz, 2H),
a Reaction conditions: substrate 1 (0.2 mmol), PhI(OAc)2 (2
equiv.) and KI (3 equiv.) in MeCN (2 mL) at room temperature
for 8-12 h. b Isolated yield.
7.35–7.32 (m, 2H), 7.16 (s, 1H), 7.13–7.07 (m, 3H), 2.20 (s, 3H); 13
C
NMR (125 MHz, CDCl3) δ: 189.3, 169.6, 155.6, 134.1, 133.2, 129.8,
129.4, 128.7, 123.7, 116.6, 93.4, 20.8; IR (KBr, cm−1): 1752, 1701;
MS (EI): 270 (M+), 227, 105, 43. Anal. Calcd for C16H16O4: C, 71.10;
H, 5.22. Found: C, 71.05; H, 5.19%.
transformed into the desired product 2l and 2m in 78% and
76% yields, respectively. However, the reaction of substrate
2-phenoxy-1-phenylpropan-1-one (1o) was unsucceseful
under the optimal conditions (entries 14).
1
2-Oxo-1-phenoxy-2-p-tolylethyl acetate (2c): Yellow oil; H NMR
(500 MHz, CDCl3) δ: 7.95 (d, J = 8.5 Hz, 2H), 7.35–7.32 (m, 2H),
7.27 (d, J = 8.0 Hz, 2H), 7.15 (s, 1H), 7.12–7.06 (m, 3H), 2.41 (s, 3H),
Scheme 1 A working mechanism.

348 JOURNAL OF CHEMICAL RESEARCH 2011
2.20 (s, 3H); 13C NMR (125 MHz, CDCl3) δ: 188.9, 169.7, 155.6,
145.2, 130.7, 129.8, 129.5, 129.4, 123.6, 116.6, 93.3, 21.8, 20.8; IR
(KBr, cm−1): 1752, 1700; MS (EI): 284 (M+), 241, 119, 43. Anal.
Calcd for C17H16O4: C, 71.82; H, 5.67. Found: C, 71.76; H, 5.60%.
2-(4-Methoxyphenyl)-2-oxo-1-phenoxyethyl acetate (2d): Yellow
oil; 1H NMR (500 MHz, CDCl3) δ: 8.04 (d, J = 9.0 Hz, 2H), 7.34–7.31
(m, 2H), 7.13 (s, 1H), 7.11–7.06 (m, 3H), 6.94 (d, J =8.5 Hz, 2H), 3.85
(s, 3H), 2.19 (s, 3H); 13C NMR (125 MHz, CDCl3) δ: 187.7, 169.6,
164.2, 155.6, 131.8, 129.8, 126.0, 123.5, 116.5, 113.9, 93.4, 55.4,
20.8; IR (KBr, cm−1): 1752, 1700; MS (EI): 300 (M+), 257, 135, 43.
Anal. Calcd for C17H16O5: C, 67.99; H, 5.37. Found: C, 67.87; H,
5.28%.
2-(4-Fluorophenyl)-2-oxo-1-phenoxyethyl acetate (2e): Yellow oil;
1H NMR (500 MHz, CDCl3) δ: 8.12–8.09 (m, 2H), 7.36–7.33 (m, 2H),
7.17–7.14 (m, 3H), 7.12 (s, 1H), 7.11–7.05 (m, 2H), 2.21 (s, 3H);
13C NMR (125 MHz, CDCl3) δ: 188.0, 169.6, 155.4, 138.3, 132.3,
132.3, 129.9, 129.5, 123.8, 116.6, 93.6, 20.8; IR (KBr, cm−1): 1752,
1700; MS (EI): 288 (M+), 245, 123, 43. Anal. Calcd for C16H13FO4:
C, 66.66; H, 4.55. Found: C, 66.58; H, 4.47%.
2-(Naphthalen-2-yl)-2-oxo-1-phenoxyethyl acetate (2f): Yellow
solid, m.p. 79.1–81.1 °C (uncorrected);1H NMR (500 MHz, CDCl3)
δ: 8.53 (s, 1H), 7.98 (d, J = 7.5 Hz, 1H), 7.84–7.77 (m, 3H), 7.54–7.51
(m, 1H), 7.47–7.44 (m, 1H), 7.27 (d, J = 2.5 Hz, 2H), 7.20 (d, J =
2.5 Hz, 1H), 7.05–7.02 (m, 3H), 2.14 (s, 3H); 13C NMR (125 MHz,
CDCl3) δ: 189.4, 169.8, 155.7, 136.0, 132.4, 131.8, 130.6, 130.0,
129.2, 128.7, 127.9, 127.0, 124.5, 123.8, 116.8, 93.7, 21.0; IR (KBr,
cm−1): 1753, 1702; MS (EI): 320 (M+), 277, 155, 43. Anal. Calcd for
C20H16O4: C, 74.99; H, 5.03. Found: C, 74.90; H, 4.97%.
δ: 8.02–8.00 (m, 3H), 7.72 (d, J = 8.0 Hz, 1H), 7.52–7.49 (m, 2H),
7.41–7.31 (m, 5H), 7.27 (s, 1H), 7.05 (d, J = 8.0 Hz, 1H), 2.12 (s, 3H);
13C NMR (125 MHz, CDCl3) δ: 189.3, 169.7, 151.5, 134.6, 134.1,
133.2, 129.4, 128.7, 127.5, 126.7, 125.9, 125.7, 125.5, 123.3, 121.8,
108.1, 93.5, 20.8; IR (KBr, cm−1): 1754, 1702; MS (EI): 320 (M+),
277, 105. Anal. Calcd for C20H16O4: C, 74.99; H, 5.03. Found:
C, 74.89; H, 4.95%.
2-Oxo-2-phenyl-1-(quinolin-8-yloxy)ethyl acetate (2m):Yellow oil;
1H NMR (500 MHz, CDCl3) δ: 8.79–8.78 (m, 1H), 8.35 (d, J = 8.5 Hz,
2H), 8.16–8.14 (m, 1H), 7.71 (s, 1H), 7.60–7.57 (m, 2H), 7.50–7.39
(m, 5H), 2.15 (s, 3H); 13C NMR (125 MHz, CDCl3) δ: 169.6, 151.3,
149.2, 140.4, 136.2, 133.8, 133.7, 129.7, 129.6, 128.6, 126.5, 123.6,
121.6, 117.5, 94.0, 20.8; IR (KBr, cm−1): 1758, 1709; MS (EI):
321 (M+), 278, 105, 43. Anal. Calcd for C19H15NO4: C, 71.02; H, 4.71;
N, 4.36. Found: C, 70.92; H, 4.63; N, 4.32%.
2-Oxo-2-phenylethyl acetate (2n) 26: White solid; M.p. 48–50 °C
(uncorrected); 1H NMR (500 MHz, CDCl3) δ: 7.95 (d, J = 7.0 Hz, 2H),
7.60 (t, J = 4.5 Hz, 1H), 7.47 (t, J = 8.0Hz, 2H), 5.36 (s, 2H), 2.24
(s, 3H); 13C NMR (125 MHz, CDCl3) δ: 190.2, 169.5, 134.2, 133.9,
128.7, 125.7, 65.8, 20.8; IR (KBr, cm−1): 1751, 1701; MS (EI):
178(M+), 105.
We thank the Scientific Research Fund of Hunan Provincial
Education Department (No. 09C229) and National Natural
Science Foundation of China (No. 20872112) for financial
support.
Received 22 February 2011; accepted 27 May 2011
Paper 1100587 doi: 10.3184/174751911X13081595869649
Published online: 11 July 2011
1-(2-Methoxyphenoxy)-2-oxo-2-phenylethyl acetate (2g): Yellow
solid, m.p. 80.1–82.3 °C (uncorrected); 1H NMR (500 MHz, CDCl3)
δ: 8.22–8.20 (m, 2H), 7.62–7.58 (m, 1H), 7.50–7.47 (m, 2H), 7.14–
7.09 (m, 3H), 6.93–6.88 (m, 2H), 3.80 (s, 3H), 2.16 (s, 3H); 13C NMR
(125 MHz, CDCl3) δ: 189.9, 169.5, 150.9, 144.3, 133.8, 133.5, 129.5,
128.5, 125.3, 121.0, 120.8, 112.5, 94.1, 55.6, 20.8; IR (KBr, cm−1):
1752, 1700; MS (EI): 300 (M+), 257, 105, 43.Anal. Calcd for C17H16O5:
C, 67.99; H, 5.37. Found: C, 67.89; H, 5.30%.
1-(3-Methoxyphenoxy)-2-oxo-2-phenylethyl acetate (2h): Yellow
solid, m.p. 79.1–81.6 °C (uncorrected); 1H NMR (500 MHz, CDCl3)
δ: 8.05–8.03 (m, 2H), 7.62–7.59 (m, 1H), 7.49–7.46 (m, 2H), 7.25–
7.22 (m, 1H), 7.15 (s, 1H),6.68–6.65 (m, 2H), 6.63 (t, J =2.5 Hz, 1H),
3.780 (s, 3H), 2.20 (s, 3H); 13C NMR (125 MHz, CDCl3) δ: 189.2,
169.6, 160.9, 156.7, 134.1, 133.1, 130.3, 129.4, 128.7, 109.3, 108.1,
103.0, 93.2, 55.3, 20.8; IR (KBr, cm−1): 1752, 1700; MS (EI): 300
(M+), 257, 105, 43. Anal. Calcd for C17H16O4: C, 67.99; H, 5.37.
Found: C, 67.88; H, 5.29%.
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9.0 Hz, 1H), 7.64–7.61 (m, 1H), 7.52–7.49 (m, 2H), 7.35–7.32 (m,
1H), 7.15 (s, 1H), 7.09 (d, J = 8.0 Hz, 2H), 6.87–6.84 (m, 1H), 2.21 (s,
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1-(4-Chlorophenoxy)-2-oxo-2-phenylethyl acetate (2j): Yellow oil;
1H NMR (500 MHz, CDCl3) δ: 7.95 (d, J = 7.5 Hz, 2H), 7.54 (t, J =
7.5 Hz, 1H), 7.42-7.40 (m, 2H), 7.28–7.20 (m, 2H), 7.02 (s, 1H),
6.95–6.92 (m, 2H), 2.14 (s, 3H); 13C NMR (125 MHz, CDCl3)
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93.4, 20.8; IR (KBr, cm−1): 1752, 1701; IR (KBr, cm−1): 1753, 1702;
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C, 63.06; H, 4.30. Found: C, 62.98; H, 4.23%.
1-(2-Allylphenoxy)-2-oxo-2-phenylethyl acetate (2k): Yellow oil;
1H NMR (500 MHz, CDCl3) δ: 8.05 (d, J = 7.5 Hz, 2H), 7.62–7.59
(m, 1H), 7.47 (t, J =8.0 Hz, 2H), 7.25–7.19 (m, 2H), 7.14 (s, 1H),
7.09–7.05 (m, 2H), 5.86–5.79 (m, 1H), 4.95–4.90 (m, 2H), 3.31 (d,
J = 6.5 Hz, 2H), 2.19 (s, 3H); 13C NMR (125 MHz, CDCl3) δ: 189.4,
169.6, 153.4, 136.2, 134.0, 133.2, 130.6, 130.0, 129.4, 128.6, 123.5,
115.9, 113.8, 93.7, 34.1, 20.8; IR (KBr, cm−1): 1752, 1700; MS (EI):
310 (M+), 267, 105, 43. Anal. Calcd for C19H18O4: C, 73.53; H, 5.85.
Found: C, 73.43; H, 5.77%.
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J. Org. Chem., 2008, 73, 6928.
1-(Naphthalen-1-yloxy)-2-oxo-2-phenylethyl acetate (2l): Yellow
solid, m.p. 72.2–74.6 °C (uncorrected); 1H NMR (500 MHz, CDCl3)

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