Concise synthesis of 1-naphthols under mild conditions through a copper-catalyzed arylation of methyl ketones

Article abstract of DOI:10.1002/adsc.201300728

A concise synthesis of 1-naphthols via cyclization of o-iodoacetophenones and methyl ketones has been realized under very mild conditions. The cyclization process is initiated by a rare coppercatalyzed arylation of simple methyl ketones with ortho-iodoacetophenones.

Full text of DOI:10.1002/adsc.201300728

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DOI: 10.1002/adsc.201300728
Concise Synthesis of 1-Naphthols under Mild Conditions through
a Copper-Catalyzed Arylation of Methyl Ketones
Zhenbang Lou,a,b Shu Zhang,a,c Chao Chen,a,* Xinlong Pang,a,b Ming Li,b
and Lirong Wenb
a
Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of
Chemistry, Tsinghua University, Beijing 100084, Peopleꢀs Republic of China
Fax : (+86)-10-6277-31149; phone: (+86)-10-6277-3684; e-mail: chenchao01@mails.tsinghua.edu.cn
College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042,
b
Peopleꢀs Republic of China
c
Department of Applied Chemistry, China Agricultural University, Beijing 100193, Peopleꢀs Republic of China
Received: August 12, 2013; Revised: October 16, 2013; Published online: January 10, 2014
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201300728.
Abstract: A concise synthesis of 1-naphthols via
cyclization of o-iodoacetophenones and methyl ke-
tones has been realized under very mild conditions.
The cyclization process is initiated by a rare copper-
catalyzed arylation of simple methyl ketones with
ortho-iodoacetophenones.
derivatives, or diketones is well known and more re-
cently the Cu-catalyzed a-arylation of benzyl phenyl
ketones has also been realized.[4] One-pot strategies
for the synthesis of various useful cyclic compounds
based on the Cu-catalyzed a-arylation of activated ke-
tones have been investigated, but rarely applied to
simple methyl ketones.[5,6] Herein, we would like to
report a facile construction of 1-naphthols via cycliza-
tion from ortho-iodoacetophenones[7] and methyl ke-
tones catalyzed by CuI. The reaction was realized
under mild conditions initiated by a rare Cu-catalyzed
arylation of simple methyl ketones (Scheme 1).
Keywords: arylation; copper-catalyzed reaction;
ortho-iodoacetophenones; methyl ketones; 1-naph-
thols
During our study on synthesizing cyclic compounds
with copper catalysts,[8] we found the formation of
1-Naphthols are important classes of organic com- naphthol 3a in the reaction of ortho-iodoacetophen-
pounds that are not only applied in organic synthesis, one 1a with acetophenone 2a under simple Cu-cata-
AHCTUNGTRENNUNG
organic catalysts and as ligands for transition-metal lyzed conditions (Table 1). When 1.0 mmol of ortho-
catalysts, but they also occur in numerous natural iodoacetophenone 1a was treated with acetophenone
products and pharmaceuticals as privileged scaf- 2a (3 equiv.) in the presence of NaO-t-Bu (base,
folds.[1] Therefore, synthetic chemists have made great 4 equiv.), CuI (catalyst, 10 mol%) and 1,10-phen
efforts in the development of new and efficient meth- (1,10-phenanthroline, ligand, 20 mol%) in toluene at
odologies for the synthesis of polysubstituted 1-naph-
thol derivatives.[2] Meanwhile, the synthesis of naph-
thalene derivatives has made much progress, especial-
ly aided by transition metals[3] and some of the syn-
theses are also applicable to 1-naphthols. Neverthe-
less, the present synthetic methods to 1-naphthols
often require complicated starting materials (most of
them are not readily available),[2a–d,f–g,i,j] precious cata-
lysts,[2e,3i] high temperature and/or a prolonged reac-
tion time.[2h,3h–i] To date, the facile construction of mul-
tisubstituted 1-naphthols from readily available start-
ing materials under mild conditions still remains a big
challenge.
Scheme 1. Concise synthesis of 1-naphthols via cyclization of
ortho-iodoacetophenones and methyl ketones under mild
The Cu-catalyzed a-arylation of highly activated
carbonyl compounds such as keto esters, malonic acid conditions.
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Table 1. Optimization of reaction conditions for the formation of 3a.
Entry
CuI (equiv.)
1,10-phen (equiv.)
NaO-t-Bu (equiv.)
Ratio of 1a:2a
Temperature [oC]
Yield [%][a]
1
2
3
4
5
6
7
8
10%
10%
10%
10%
10%
10%
10%
10%
10%
5%
10%
0
10%
10%
10%
20%
20%
20%
20%
20%
20%
20%
20%
20%
10%
0
4
3
5
6
6
6
6
6
6
6
6
6
6
6
6
1:3
1:3
1:3
1:3
1:3
1:3
1:3
1:1
1:2
1:3
1:3
1:3
1:3
1:3
1:3
25
25
25
25
0
40
60
25
25
25
25
25
0
30
trace
74
87 (85)
62
85
37
24
75
37
51
trace
0
0
0
9
10
11
12
13[b]
14[b]
15[b]
20%
20%
20%
20%
30
60
[a]
GC yield with n-dodecane as internal standard (isolated yield in brackets).
ortho-Bromoacetophenone was used instead of 2-iodoacetophenone.
[b]
room temperature for 4.5 h, 3-phenyl-1-naphthol 3a sitions all worked well to give 3-substituted phenyl-1-
was formed in 30% yield (entry 1). To date, there naphthols. Substrates with electron-withdrawing
have been seven other methods reported for the syn- groups and halo groups gave the products in higher
thesis of 3-phenyl-1-naphthol 2a in multi-step proce- yields than those with electron-donating groups. Be-
dures suffering from harsh conditions.[9] Considering sides those with substituted phenyl groups, substrates
the importance of this compound and the easy manip- with 1- and 2-naphthyl, 1-furanyl and 1-thienyl groups
ulation of our method, we were encouraged to per- also reacted well with 1a to give 3-aryl-1-naphthols.[9]
form an optimization study on bases, solvents, cata- Excitingly, acetone 2r could react with 1a at À208C to
lysts and ligands (see the Supporting Information for give 3-methyl-1-naphthol 3r in a synthetically useful
details). Gratifyingly, we found NaO-t-Bu was the yield. Interestingly, the reaction of 2-butanone 2s with
best base for this reaction and the amount of NaO-t- 1a at À208C only afforded 3-ethyl-1-naphthol 3s in
Bu was crucial: 3a was formed in 74% yield with 54% yield suggesting that the reactivity of a methyl
5 equiv. of NaO-t-Bu, and in 87% yield with 6 equiv. group was higher than that of an ethyl group in 2-bu-
of NaO-t-Bu. The decreased loading of 2a also affect- tanone (entry 19). Finally, the reaction of 1-phenyl-1-
ed the yield of 3a (entries 8 and 9). Under otherwise propanone 2t with 1a at room temperature produced
the same conditions without CuI, no product was 3-phenyl-4-methyl-1-naphthol 3t in 48% yield
formed (entry 12). After lots of attempts, the optimal (entry 20).
conditions were found as shown in entry 4 with the
After the successful preparation of naphthol with
following parameters: CuI as a precatalyst (10%), substituents on the phenol ring, we turned to intro-
1,10-phen as a ligand (20%), NaO-t-Bu as a base duce more substituents by using substituted ortho-
(6 equiv.), toluene as a solvent at 258C, and a ratio of iodoacetophenones 1 with methyl ketones 2 (Table 3).
1a:2a=1:3. We also investigated the reaction of 5-Bromo-2-iodoacetophenone 1b was first reacted
ortho-bromoacetophenone with acetophenone, how- with acetophenone 2a under standard conditions and
ever, the reaction did not occur under our standard 1-naphthol 4a was obtained in 76% yield with the
conditions even at 608C (entries 13–15).
bromine atom intact. We examined more reactions of
Under these optimized conditions, a study on the 1b with other methyl ketones and 1-naphthols 4b–4e
substrate scope of methyl ketones 2 was carried out were isolated in good yields with the bromine atom
with 1a, and the results are listed in Table 2. General- being retained in all cases (entries 1–5). Other ortho-
ly, acetophenones 2 with a range of substitutents such iodoacetophenones with substituents such as phenyl,
as methyl, trifluoromethyl, cyano, fluoro, chloro, phenylethynyl, and dioxylyl groups also worked well
bromo and phenyl groups at ortho-, meta- or para-po-
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Concise Synthesis of 1-Naphthols under Mild Conditions
Table 2. Naphthols 3 formed from the reaction of ortho-
iodoacetophenone 1a with various methyl ketones 2.
Table 2. (Continued)
[a]
Isolated yields.
Performed at À208C.
[b]
to produce the corresponding 1-naphthols in good
yields (entries 6–11).
To get an insight of the mechanism, 2,5-diiodoace-
tophenone 1f was prepared and reacted with aceto-
phenone 2a and acetone 2r. Interestingly, only the 2-
iodo atoms of 2a and 2r were substituted giving naph-
thols 4l and 4m while the 5-iodo atoms remained
intact [Scheme 2, Eq. (1)]. This result implied that the
2-iodo atom was activated by an acetyl group in com-
pound 1 during the Cu-catalyzed reaction. Additional-
ly, the aldol condensation product 7 was separately
prepared from 1a and 3r via classic Mukaiyama reac-
tion followed by dehydration.[10] Treatment of 7 under
the standard conditions for the formation of 1-naph-
thols failed to generate 3r. This result suggested that
the aldol condensation product 7 was not an inter-
mediate for the formation of 1-naphthols.
Based on the results above, we proposed the fol-
lowing mechanism (Scheme 3): the reaction of 1 with
CuI and 1,10-phen via oxidative addition provides
CuACTHNUGRTENUNG(III) species I, which is stabilized by the intramo-
lecular coordination of a carbonyl group. Meanwhile,
the methyl ketone is deprotonated by NaO-t-Bu to
give enolate II. The reaction of I and enolate II via
transmetallation affords III, and reductive elimination
of III (C-arylation of methyl ketone) gives IV, regen-
erating the copper catalyst. The transformation of IV
into naphthol via aldol reaction, dehydration and tau-
tomerization was realized in the presence of NaO-t-
Bu as reported in the previous study.[9,11]
As a convenient method to prepare 1-naphthols,
the reaction was also performed in a scale of
10 mmol. To our delight, product 3a was isolated in
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Zhenbang Lou et al.
Table 3. Naphthols 4 formed from the reaction of various
substituted ortho-iodoacetophenones 1 with methyl ketones
2.
under an N2 atmosphere, product 3a was isolated in
85% yield.
In conclusion, we have developed a cyclization re-
action for the synthesis of 1-naphthols under mild
conditions with readily available starting materials:
ortho-iodoacetophenones 1 and simple methyl ke-
tones 2. The process was initiated by a rare Cu-cata-
lyzed arylation of simple methyl ketones and could
tolerate various functional groups in the substrates
providing the opportunity for further transformations.
Therefore, we believe this method will find many ap-
plications in organic chemistry and medicinal chemis-
try.
Experimental Section
Representative Procedure of the Synthesis of 3a
A sealed tube was charged with a mixture of CuI (0.1 mmol,
19.0 mg), 1,10-phen (0.2 mmol, 36.0 mg) and NaO-t-Bu
(6 mmol, 0.576 g). After being evacuated and recharged
with N2 for 3 times, 2-iodoacetophenone 1a (1.0 mmol) and
acetophenone 2a (3.0 mmol) were added into the tube.
After toluene (2.0 mL) had been added, the tube was sealed
and the mixture was allowed to stir at room temperature for
4.5 h. Afterwards, 2N aqueous HCl was added and the mix-
ture was extracted with Et2O (5 mLꢂ3). The organic phase
was combined and dried over anhydrous Na2SO4. Evapora-
tion of the solvent followed by purification on silica gel (pe-
troleum ether/diethyl ether: 25/1 to 10/1) provided 3-phenyl-
1-naphthol (3a) as a light yellow solid; yield: 191 mg
(85%).[9] 1H NMR (301 MHz, CDCl3): d=8.23 (d, J=
7.7 Hz, 1H), 7.89 (dd, J=6.8, 2.1 Hz, 1H), 7.69–7.65 (m,
3H), 7.56–7.46 (m, 4H), 7.44–7.39 (m, 1H), 7.08 (d, J=
1.5 Hz, 1H), 5.65 (broad, 1H); 13C NMR (76 MHz, CDCl3):
d=151.9, 141.0, 139.0, 135.1, 129.0 (2ꢂCH), 128.2, 127.6,
127.4ACTHNURTGNEU(GN 2ꢂCH), 127.0, 125.5, 123.8, 121.6, 118.9, 108.6; GC-
MS: m/z=220 (M+); ESI-HR-MS: m/z=219.0819, calcd. for
C16H12O [MÀH]À: 219.0815.
[a]
Isolated yields.
Performed at À208C.
Representative Procedure of the Synthesis of 3r
[b]
A sealed tube was charged with a mixture of CuI (0.1 mmol,
19.0 mg), 1,10-phen (0.2 mmol, 36.0 mg) and NaO-t-Bu
74% yield [Eq. (2)]. Additionally, when the reaction
was performed in a two-necked round-bottom flask (6 mmol, 0.576 g). After evacuated and recharged with N2
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Concise Synthesis of 1-Naphthols under Mild Conditions
Scheme 2. The mechanistic study of Cu-catalyzed synthesis of 1-naphthols.
Scheme 3. Proposed mechanism.
for 3 times, 2-iodoacetophenone 1a (1.0 mmol) and acetone
2r (3.0 mmol) were added into the tube. After toluene
(2.0 mL) had been added, the tube was sealed and the mix-
ture was allowed to stir at À208C for 4.5 h. Afterwards, 2N
aqueous HCl was added and the mixture was extracted with
Et2O (5 mLꢂ3). The organic phase was combined and dried
over anhydrous Na2SO4. Evaporation of the solvent fol-
lowed by purification on silica gel (petroleum ether/diethyl
ether: 25/1 to 10/1) provided 3-methyl-1-naphthol (3r) as
127.2, 126.6, 124.5, 122.7, 121.5, 119.9, 112.0, 21.9; GC-MS:
m/z=158 (M+); ESI-HR-MS: m/z=157.0730, calcd. for
C11H10O [MÀH]À: 157.0732.
Acknowledgements
This work was supported by National Natural Science Foun-
dation of China (21102080, 21372138) and Tsinghua Univer-
sity Initiative Scientific Research Program (2011Z02150).
a
light yellow solid; yield: 98 mg (62%).[12] 1H NMR
(400 MHz, CDCl3): d=8.12 (dd, J=7.8, 1.2 Hz, 1H), 7.74
(dd, J=7.4, 1.8 Hz, 1H), 7.45 (ddd, J=7.5, 2.7, 1.4 Hz, 2H),
7.24 (s, 1H), 6.65 (d, J=1.2 Hz, 1H), 5.24 (s, 1H), 2.45 (s,
3H); 13C NMR (101 MHz, CDCl3): d=151.2, 136.0, 135.0,
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COMMUNICATIONS
Concise Synthesis of 1-Naphthols under Mild Conditions
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