Reformatsky-type reaction of α-haloketones promoted by titanium tetraiodide

Article abstract of DOI:10.1016/S0040-4020(01)00982-6

Titanium(IV) tetraiodide induces a Reformatsky-type reaction of α-iodoketones with carbonyl compounds to give β-hydroxy ketones in good to high yields.

Full text of DOI:10.1016/S0040-4020(01)00982-6

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TETRAHEDRON
Pergamon
Tetrahedron 57 %2001) 9591±9595
Reformatsky-type reaction of a-haloketones promoted by
titanium tetraiodide
Makoto Shimizu,p Fumiko Kobayashi and Ryuuichirou Hayakawa
Department of Chemistry for Materials, Mie University, Tsu, Mie 514-8507, Japan
Received 7 September 2001;accepted 5 October 2001
AbstractÐTitanium%IV) tetraiodide induces a Reformatsky-type reaction of a-iodoketones with carbonyl compounds to give b-hydroxy
ketones in good to high yields. q 2001 Elsevier Science Ltd. All rights reserved.
1. Introduction
facile reductions. In particular, the ability of the iodide
ion to displace the iodine a to the carbonyl appears to be
responsible for the facile aldol type reaction of methoxy-
allene oxide recently published,5c and therefore, we focus on
the applicability of titanium iodide to the formation of
enolates from a-iodoketones and subsequent aldol type
reactions. In this paper, we describe titanium tetraiodide
promoted reaction of a-haloketones with aldehydes to
give b-hydroxy ketones in good yields %Eq. %2)). Table 1
summarizes the results of the addition reaction of a-iodo-
acetophenone to benzaldehyde in the presence of titanium
tetraiodide under a variety of reaction conditions.
First discovered by Reformatsky in 1887, the reaction of
a-halocarbonyl compounds and aldehydes in the presence
of zinc is the ®rst example of a large member of now
commonly used carbon±carbon bond forming reactions.1
Reductive formation of enolate species %or their equiva-
lents) makes the reaction proceed under essentially neutral
conditions %Eq. %1)). However, the yields of this type of
reaction are not always satisfactory. This arises from the
low reactivity of zinc metal and of the resulting organo-
metallic reagent: the reaction usually has to be carried out
at a high temperature, which causes concurrent undesirable
side reactions and/or competitive reactions through several
alternate transition states. Recently, several improvements
have been made using activated Zn,2a Al,2b Sn,2c Co,2d Cr,2e
Sm,2f Ti%II)2g and so on. However, most of them use low
valent metals, which sometimes causes undesirable side
reactions involving dehydration and reduction of unsatu-
ration. It was reported that a,b-unsaturated ketones were
produced via aldol and successive dehydration reactions
of a-bromacetophenone with various aldehydes using
TiCl4 and KI,3a and also some improvements made possible
the isolation of aldols before dehydration.3b Very recently, a
combined use of TiCl4 and R4NI was reported to be a good
tool for aldol reaction of a-haloketones.4
ꢀ1†
ꢀ2†
As shown in Table 1, when the reaction was carried out with
a slight excess of TiI4, the desired aldol adduct 2 was
obtained in good yield %entry 4). In terms of product yield
and the amounts of reagents, the reaction conditions used
in entry 6 were employed to compare the effects of halogen
in Ti and a-haloacetophenone 1. When the iodine ligand in
TiX4 was replaced with chlorine or bromine, the reaction
did not give the desired product 2 or gave it in low yield,
respectively %entries 7 and 8). Replacement of the halogen
in 1 also did not give the adduct 2 in satisfactory yields
%entries 9 and 10). Thus, for the reductive formation of Ti
enolate, the use of TiI4 with a-iodocarbonyl compounds
proved to be necessary. Under the optimum conditions,
the addition reaction of a variety of a-haloketones with
aldehydes in the presence of titanium tetraiodide are
summarized in Table 2.
2. Results and discussion
We have recently found that TiI4 is an excellent reagent for
the reduction of a-diketones and/or sulfoxides, and that it
also induces ring-opening-aldol reaction of methoxyallene
oxide and pinacol coupling of aldehyhdes.5 In these
reactions, Ti%IV) was thought to be responsible for such
Keywords: Reformatsky-type reaction;titanium tetraiodide; a-haloketones.
Corresponding author. Tel./fax: 181-59-231-9413;
e-mail: mshimizu@chem.mie-u.ac.jp
p
0040±4020/01/$ - see front matter q 2001 Elsevier Science Ltd. All rights reserved.
PII: S0040-4020%01)00982-6

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M. Shimizu et al. / Tetrahedron 57 &2001) 9591±9595
Table 1. Reaction of a-haloacetophenone 1 with benzaldehyde
Entry
X
TiX4 %equiv.)
PhCHO %equiv.)
Temperature %8C)
Time %h)
Yield %%)a
1
2
3
4
5
6
7
8
9
10
I
I
I
I
I
I
I
I
TiI4 %1.2)
TiI4 %1.5)
TiI4 %2.0)
TiI4 %1.2)
TiI4 %1.2)
TiI4 %1.2)
TiCl4 %1.5)
TiBr4 %1.5)
TiI4 %1.5)
TiI4 %1.5)
1.1
1.1
1.1
1.5
2.0
1.5
1.5
1.5
1.5
1.5
295 to 210
295 to 210
295 to 210
278 to 220
278 to 220
278 to 260
278 to 260
278 to 260
278 to 260
278 to 260
5.5
5.0
5.0
3.0
3.0
1.0
1.0
1.0
1.0
1.0
76
65
56
85
84
83
0
13
0
38
Cl
Br
a
Isolated yield.
Table 2. Reaction of a-iodoketone with aldehyde in the presence of TiI4
Entry
R1
Ph
R2
R3
p-ClC6H4
p-MeOC6H4
p-HOC6H4
PhCH2CH2
trans-CH3CHvCH
n-Bu
c-Hex
i-Pr
t-Bu
Ph
PhCH2CH2
Ph
PhCH2CH2
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Additive %equiv.)
Yield %%)a
anti/synb
1
2
3
4
5
6
7
8
H
H
H
H
H
H
H
H
H
H
H
H
None
None
None
None
None
None
None
None
None
None
None
None
None
94
90
77
69
56
64
73
49
34
58
57
52
50
87
91
76
90
88
81
80
±
±
±
±
±
±
±
±
±
±
±
±
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Et
9
10
11
12
13
14
15
16
17
18c
19
20
Et
t-Bu
t-Bu
Ph
Ph
Ph
Ph
Ph
H
±
Me
Me
Me
Me
Me
None
53:47
47:53
73:27
71:29
9:91
48:52
75:25
Ti%OiPr)4 %1.1)
BF3´Et2O %1.1)
iPr2EtN %0.6)
2-Methyl-2-butene %3.0)
None
±%CH2)4±
±%CH2)4±
BF3´Et2O %1.5)
a
Isolated yield.
Determined by H NMR.
Carried our in 1,4-dioxane at room temperarture.
b
c
1
As shown in Table 2, a-iodoacetophenone smoothly reacted
with aromatic, aliphatic, and a,b-unsaturated aldehydes to
give aldol products in good to excellent yields %entries 1±9).
Hydroxy group on the aromatic ring did not affect addition
reaction, and the aldol adduct was obtained in good yield
%entry 3). The present reaction is sensitive to the steric
congestion around the aldehyde carbon, and as the bulkiness
of the a-substituent increased, the product yield became low
%entries 6±9). Aliphatic iodomethyl ketones also partici-
pated in the present reaction, and the b-hydroxy ketones
were obtained in moderated yield %entries 10±13). Dia-
stereoselectivity was examined using a-iodopropiophenone
and a-iodocyclohexanone. While in the absence of additives
no selectivity was observed %entries 14 and 19), addition of
i
BF3´Et2O and/or Pr2NEt promoted the formation of anti
adducts %entries 16, 17, and 20). Interestingly, the reaction
in the presence of 2-methyl-2-butene in 1,4-dioxane which
is known to form a complex with halogen completely
altered the diastereoselectivity, and the syn-adduct was
obtained as a major product %entry 18). This may be due
Scheme 1.

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M. Shimizu et al. / Tetrahedron 57 &2001) 9591±9595
9593
Puri®cation by preparative TLC on silica gel %n-hexane/
ethyl acetateˆ8:1) gave the title compound %38.3 mg, 83%).
1H NMR %CDCl3) d 3.37 %d, Jˆ6.1 Hz, 2H), 3.59 %brs, 1H),
5.34 %t, Jˆ6.1 Hz, 1H), 7.26±7.61 %m, 8H), 7.93±7.97 %m,
2H). IR %neat) 3440, 3050, 1690, 1460, 1220, 755, 705,
690 cm21. The spectral data are in accordance with those
in the literature.8
4.1.2. 3-'4-Chlorophenyl)-3-hydroxy-1-phenylpropanan-
1-one. 1H NMR %CDCl3) d 3.32 %d, Jˆ1.3 Hz, 1H), 3.34 %s,
1H), 3.67 %d, Jˆ3.0 Hz, 1H), 5.29±5.34 %m, 1H), 7.31±7.50
%m, 7H), 7.92±7.96 %m, 2H). IR %neat) 3440, 3070, 1685,
1500, 1460, 1225, 1025, 840, 760, 690 cm21. The spectral
data are in accordance with those in the literature.3b
Scheme 2.
to the ability of 2-methyl-2-butene to trap the iodine and/or
hydrogen iodide formed concomitantly, and to suppress the
isomerization of the initially formed %Z)-enolate and/or syn-
aldol.6 Furtheremore, acetals also participated in the present
reaction to give the b-alkoxy ketone 5 in good yield
%Scheme 1).
4.1.3. 3-Hydroxy-3-'4-methoxyphenyl)-1-phenylpropan-
1-one. 1H NMR %CDCl3) d 3.34 %s, 1H), 3.36 %d, Jˆ3.3 Hz,
1H), 3.53 %br, 1H), 3.80 %s, 3H), 5.36±5.31 %m, 1H), 6.88±
6.92 %m, 2H), 7.34±7.37 %m, 2H), 7.42±7.48 %m, 2H), 7.54±
7.60 %m, 1H), 7.93±7.96 %m, 2H). IR %neat) 3440, 1690,
1525, 1260, 1185, 1040, 840, 765, 695 cm21. MS m/z
241.20 [M2CH3], 213.24 [M2CH3±CO].
The present reaction most probably proceeds as follows:
TiI4 reduces a-iodoketone to form Ti-enolate 6 via the
attack of some nucleophile involving iodide anion to the
iodine. The formation of the metal enolate via attack of
iodide anion has been well precedented.7 Subsequent
reaction with aldehyde gives the aldol adduct %Scheme 2).
4.1.4. 3-Hydroxy-3-'4-hydroxyphenyl)-1-phenylpropan-
1
1-one. H NMR %CDCl3) d 3.35 %d, Jˆ4.3 Hz, 1H), 3.37
%d, Jˆ7.9 Hz, 1H), 3.81 %brs, 1H), 5.26 %dd, Jˆ4.3, 7.9 Hz,
1H), 6.31 %brs, 1H), 6.73±6.78 %m, 2H). 7.22±7.26 %m, 2H),
7.42±7.61 %m, 3H), 7.92±7.95 %m, 2H). IR %CHCl3) 3320,
1680, 1605, 1520, 1460, 1220, 840, 760, 695 cm21. MS m/z
225.27 [M2H2O].
3. Conclusion
In conclusion, TiI4 promotes the reaction of a-iodoketones
with aldehydes to give aldol products in good to excellent
yields, where the reductive formation of Ti enolate without
the use of low valent metal species is noteworthy.
4.1.5. 3-Hydroxy-1,5-diphenylpentan-1-one. 1H NMR
%CDCl3) d 1.74±2.02 %m, 2H), 2.70±2.94 %m, 2H), 3.01±
3.20 %m, 2H), 3.38 %d, Jˆ2.6 Hz, 1H), 4.19±4.29 %m, 1H),
7.15±7.61 %m, 8H), 7.91±7.95 %m, 2H). IR %neat) 3450,
3000, 1690, 1605, 1590, 1505, 1460, 1300, 1220, 750,
700, 595 cm21. The spectral data are in accordance with
those in the literature.3b
4. Experimental
4.1. General
4.1.6. 3-Hydroxy-1-phenyl-4-hexen-1-one. 1H NMR
%CDCl3) d 1.72 %d, Jˆ6.4 Hz, 3H), 3.13 %brs, 1H), 3.17 %d,
Jˆ2.3 Hz, 1H), 3.19 %s, 1H), 4.70 %dd, Jˆ6.3, 12.2 Hz, 1H),
5.55±5.64 %m, 1H), 5.73±5.86 %m, 1H), 7.44±7.62 %m, 3H),
7.94±7.97 %m, 2H). IR %neat) 3440, 1690, 1605, 1455, 1270,
1025, 1010, 975, 770, 750, 700 cm21. The spectral data are
in accordance with those in the literature.9
Infrared spectra were determined on a JASCO IR-810
spectrometer. H NMR spectra were recorded with JNM
1
EX-270 spectrometers using tetramethylsilane as an internal
standard. Exact mass spectra were taken on a Waters micro-
mass ZQ. Propionitrile and 1,4-dioxane were distilled from
calcium hydride. Puri®cation of products was performed by
column chromatography on silica gel Merck Silica Gel-60,
and/or preparative TLC on silica gel Merck Kisel Gel
PF254.
4.1.7. 3-Hydroxy-1-phenylheptan-1-one. 1H NMR
%CDCl3) d 0.93 %t, Jˆ7.1 Hz, 3H), 1.31±1.68 %m, 6H),
2.99 %brs, 1H), 3.04 %dd, Jˆ8.8, 17.5 Hz, 1H), 3.18 %dd, Jˆ
2.8, 17.5 Hz, 1H), 4.18±4.26 %m, 1H), 7.44±7.62 %m, 3H),
7.94±7.98 %m, 2H). IR %neat) 3440, 1690, 1605, 1460, 1220,
760, 695 cm21. MS [M1]: 206.13, found: 206.00.
4.1.1. 3-Hydroxy-1,3-diphenylpropan-1-one. General
procedure for the Reformatsky-type reaction. To a solu-
tion of titanium tetraiodide %135.5 mg, 0.244 mmol) in
propionitrile %1.0 mL) was added a solution of benzalde-
hyde %32.4 mg, 0.305 mmol) in propionitrile %1.0 mL) at rt
under an argon atmosphere. To the reaction mixture was
added a solution of iodoacetophenone %50.0 mg, 0.203
mmol) in propionitrile %1.0 mL) at 2788C. After being
stirred at 278 to 2608C, the reaction was quenched with
sat. aqueous NaHCO3, and 10% NaHSO3. The mixture was
®ltered through a Celite pad and extracted with ethyl acetate
%10 mL£3). The combined organic extracts were dried
over anhydrous sodium sulfate and concentrated in vacuo.
4.1.8. 3-Cyclohexyl-3-hydroxy-1-phenylpropan-1-one.
1H NMR %CDCl3) d 1.01±1.36 %m, 5H), 1.41±1.55 %m,
1H), 1.61±1.82 %m, 4H), 1.93 %brd, Jˆ12.9 Hz, 1H), 3.05
%dd, Jˆ9.1, 17.4 Hz, 1H), 3.16 %s, 1H), 3.19 %dd, Jˆ2.6,
17.4 Hz, 1H), 3.96±4.03 %m, 1H), 7.44±7.50 %m, 2H),
7.55±7.62 %m, 1H), 7.95±7.99 %m, 2H). IR %neat) 3470,
1690, 1605, 1590, 1460, 1220, 755, 690, 590 cm21. MS
[M1]: 232.15, found: 232.00.

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M. Shimizu et al. / Tetrahedron 57 &2001) 9591±9595
4.1.9. 3-Hydroxy-4-methyl-1-phenylpentan-1-one. 1H
NMR %CDCl3) d 0.99 %d, Jˆ6.6 Hz, 3H), 1.02 %d,
Jˆ6.3 Hz, 3H), 1.72±1.90 %m, 1H), 3.03 %dd, Jˆ9.4,
17.2 Hz, 1H), 3.18 %dd, Jˆ2.5, 17.2 Hz, 1H), 3.18 %d,
Jˆ3.0 Hz, 1H), 3.97±4.03 %m, 1H), 7.45±7.61 %m, 3H),
7.95±7.98 %m, 2H). IR %neat) 3475, 1690, 1610, 1220,
1010, 695 cm21. The spectral data are in accordance with
those in the literature.10
1,4-dioxane %1.0 mL) was added a solution of benzaldehyde
%32.4 mg, 0.305 mmol) in 1,4-dioxane %1.0 mL) at rt under
an argon atmosphere. To the reaction mixture was added a
solution of 2-iodopropiophenone %52.8 mg, 0.203 mmol) in
1,4-dioxane %1.0 mL) at rt. After being stirred at rt for 1 h,
the reaction was quenched with sat. aqueous NaHCO3, and
10% NaHSO3. The mixture was ®ltered through a Celite pad
and extracted with ethyl acetate %10 mL£3). The combined
organic extracts were dried over anhydrous sodium sulfate
and concentrated in vacuo. Puri®cation by preparative TLC
on silica gel %n-hexane/ethyl acetateˆ10:1) gave the title
compound %43.9 mg, 90%).
4.1.10. 4,4-Dimethyl-3-hydroxy-1-phenylpentan-1-one.
1H NMR %CDCl3) d 1.00 %s, 9H), 2.98 %dd, Jˆ10.1,
17.2 Hz, 1H), 3.13 %brs, 1H), 3.21 %dd, Jˆ1.8, 17.2 Hz,
1H), 3.90 %brd, Jˆ8.6 Hz, 1H), 7.45±7.48 %m, 2H), 7.56±
7.62 %m, 1H), 7.95±7.99 %m, 2H). IR %neat) 3480, 1690,
1605, 1590, 1370, 1310, 1220, 1080, 1020, 760, 690,
605 cm21. MS [M1]: 206.13, found: 206.00.
1
syn Isomer; H NMR %CDCl3) d 1.19 %d, Jˆ7.3 Hz, 3H),
3.66 %brs, 1H), 3.70 %dq, Jˆ3.0, 7.3 Hz, 1H), 5.25 %d, Jˆ
3.0 Hz, 1H), 7.23±7.63 %m, 8H), 7.92±7.96 %m, 2H). IR
%neat) 3440, 3035, 1690, 1605, 1585, 1505, 1460, 1225,
980, 755, 710 cm21. The spectral data are in accordance
with those in the literature.12
4.1.11. 3-Hydroxy-3-methyl-1-phenylbutan-1-one. 1H
NMR %CDCl3) d 1.35 %s, 6H), 3.16 %s, 2H), 4.13 %brs, 1H),
7.45±7.51 %m, 2H), 7.57±7.62 %m, 1H), 7.95 %d, Jˆ7.3 Hz,
2H). IR %neat) 3470, 3410, 1680, 1605, 1460, 1390, 1230,
760, 690 cm21. The spectral data are in accordance with
those in the literature.10
1
anti Isomer; H NMR %CDCl3) d 1.07 %d, Jˆ6.9 Hz, 3H),
2.96 %brs, 1H), 3.81±3.89 %m, 1H), 4.99 %d, Jˆ8.3 Hz, 1H),
7.25±7.60 %m, 8H), 7.92±7.99 %m, 2H). IR %neat) 3440,
3035, 1690, 1605, 1585, 1505, 1460, 1225, 980, 755,
710 cm21. The spectral data are in accordance with those
in the literature.12
4.1.12. 3-Methoxy-1,3-diphenylpropan-1-one. 1H NMR
%CDCl3) d 3.08 %dd, Jˆ4.5, 16.5 Hz, 1H), 3.23 %s, 3H),
3.59 %dd, Jˆ8.3, 16.5 Hz, 1H), 4.88 %dd, Jˆ4.5, 8.3 Hz,
1H), 7.29±7.57 %m, 8H), 7.92±7.96 %m, 2H). IR %neat)
3040, 1700, 1610, 1590, 1500, 1460, 1365, 1280, 1220,
1120, 1000, 760, 700, 580 cm21. MS [M1]: 240.12,
found: 240.00.
4.1.18. 2-'1-Hydroxybenzyl)cyclohexanone. To a solution
of titanium tetraiodide %135.5 mg, 0.244 mmol) in propio-
nitrile %1.0 mL) was added a solution %1.0 M in CH2Cl2) of
borontri¯uoride etherate %0.31 mL, 0.31 mmol) at 2788C
under argon atmosphere. To the mixture was added a
solution of benzaldehyde %32.4 mg, 0.305 mmol) in propio-
nitrile %1.0 mL). To the reaction mixture was added a
solution of iodoacetophenone %50.0 mg, 0.203 mmol) in
propionitrile %1.0 mL) at 2788C. After being stirred at
278 to 2608C, the reaction was quenched with sat. aqueous
NaHCO3, and 10% NaHSO3. The mixture was ®ltered
through a Celite pad and extracted with ethyl acetate
%10 mL£3). The combined organic extracts were dried
over anhydrous sodium sulfate and concentrated in vacuo.
Puri®cation by preparative TLC on silica gel %n-hexane/
ethyl acetateˆ10:1) gave the title compound %33.0 mg,
80%).
4.1.13. 1-Hydroxy-1-phenylpentan-3-one. 1H NMR
%CDCl3) d 1.06 %t, Jˆ7.3 Hz, 3H), 2.45 %q, Jˆ7.3 Hz,
2H), 2.78 %dd, Jˆ4.0, 17.5 Hz, 1H), 2.88 %d, Jˆ17.5 Hz,
1H), 3.39 %s, 1H), 5.15 %dd, Jˆ4.0, 8.6 Hz, 1H), 7.25±7.37
%m, 5H). IR %neat) 3400, 1710, 1465, 1420, 1040, 765, 710,
555 cm21. The spectral data are in accordance with those in
the literature.11
4.1.14. 3-Hydroxy-1-phenylheptan-5-one. 1H NMR
%CDCl3) d 1.05 %t, Jˆ7.3 Hz, 3H), 1.65±1.89 %m, 2H),
2.44 %q, Jˆ7.3 Hz, 2H), 2.51±2.87 %m, 4H), 3.18 %d,
Jˆ3.3 Hz, 1H), 4.02±4.09 %m, 1H), 7.15±7.31 %m, 5H). IR
%neat) 3400, 1720, 1510, 1460, 1420, 1040, 750, 710 cm21
.
anti Isomer; 1H NMR %CDCl3) d 1.22±1.81 %m, 5H), 2.05±
2.13 %m, 1H), 2.30±2.67 %m, 3H), 3.96 %d, Jˆ3.0 Hz, 1H),
4.78 %dd, Jˆ2.6, 8.9 Hz, 1H), 7.27±7.39 %m, 5H). IR %neat)
3470, 1700, 1460, 1135, 700 cm21. The spectral data are in
accordance with those in the literature.10
4.1.15. 1-Hydroxy-4,4-dimethyl-1-phenylpentan-3-one.
1H NMR %CDCl3) d 1.13 %s, 9H), 2.88 %d, Jˆ5.9 Hz, 2H),
3.58 %brs, 1H), 5.13 %t, Jˆ5.9 Hz, 1H), 7.27±7.37 %m, 5H).
IR %neat) 3435, 1715, 1490, 1380, 1085, 765, 710, 580,
560 cm21. The spectral data are in accordance with those
in the literature.8
1
syn Isomer; H NMR %CDCl3) d 1.46±1.88 %m,5H), 2.05±
2.12 %m, 1H), 2.31±2.64 %m, 3H), 3.03 %d, Jˆ3.3 Hz, 1H),
5.38±5.40 %m, 1H), 7.22±7.38 %m, 5H). IR %neat) 3470,
1700, 1460, 1135, 700 cm21. The spectral data are in
accordance with those in the literature.10
4.1.16. 2,2-Dimethyl-5-hydroxy-7-phenylheptan-3-one.
1H NMR %CDCl3) d 1.13 %s, 9H), 1.67±1.88 %m, 2H), 2.56
%dd, Jˆ8.9, 17.8 Hz, 1H), 2.69 %dd, Jˆ3.0, 17.8 Hz, 1H),
2.75±2.89 %m, 2H), 3.36 %brs, 1H), 4.02 %br, 1H), 7.15±7.31
%m, 5H). IR %neat) 3450, 1710, 1480, 1460, 1380, 1080, 750,
700 cm21
.
Acknowledgements
4.1.17. 3-Hydroxy-1,3-diphenyl-2-methylpropan-1-one.
To a solution of titanium tetraiodide %135.5 mg, 0.244
mmol) and 2-methyl-2-butene %0.06 mL, 0.609 mmol) in
This research was supported by a Grant-in-Aid for Scienti®c
Research from the Ministry of Education, Culture, Sports,