Synthesis of meta-Arylated Phenol Derivatives by Rhodium(I)-Catalyzed Arylation of Quinone Monoacetal

Article abstract of DOI:10.1002/adsc.201800778

The first selective synthesis of meta-arylphenol derivatives by arylation of quinone monoacetal is reported. The transformation was achieved under Rh(I) catalysis via a formal arylation/demethoxylation process, and valuable meta-arylphenols were obtained in high yields under mild conditions. Remarkably, an unprecedented convergent reaction pathway was assumed to be involved. (Figure presented.).

Full text of DOI:10.1002/adsc.201800778

Title: Synthesis of meta-Arylated Phenol Derivatives by Rhodium(I)-
Catalyzed Arylation of Quinone Monoacetal
Authors: Jianhang Huang, Na Liu, Tao Lu, and Xiaowei Dou
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10.1002/adsc.201800778
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Synthesis of meta-Arylated Phenol Derivatives by Rhodium(I)-
Catalyzed Arylation of Quinone Monoacetal
Jianhang Huang,a Na Liu,a Tao Lu,a,b,* and Xiaowei Doua,*
a
Department of Organic Chemistry, School of Science, China Pharmaceutical University, 639 Longmian Avenue,
Nanjing 211198, China
b
State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009,
China
Fax: (+86)-25-8618-5179; e-mail: lut163@163.com; dxw@cpu.edu.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.
Abstract. The first selective synthesis of meta-arylphenol
derivatives by arylation of quinone monoacetal is reported.
The transformation was achieved under Rh(I) catalysis via
a formal arylation/demethoxylation process, and valuable
meta-arylphenols were obtained in high yields under mild
conditions. Remarkably, an unprecedented convergent
reaction pathway was assumed to be involved.
Keywords: rhodium; meta-arylphenol; arylation; quinone
monoacetal; reaction mechanisms
Substituted phenols are not only important building
blocks in organic synthesis, but also ubiquitous
structural motifs present in natural products, bioactive
compounds, and pharmaceutical drugs.[1] Therefore,
access to diversely substituted phenols from readily
available reagents is of particular significance.
Making use of the inherent reactivity of phenols in
electrophilic aromatic substitution reactions, classical
approaches readily afford ortho- and para-
functionalized phenols. In contrast, synthesis of meta-
functionalized phenols is far more challenging, and
Scheme 1. Synthesis of meta-arylphenol derivatives.
considerable efforts have been devoted to this end in
recent years.[2] In particular, development of new
methods for the synthesis of meta-arylphenols has
attracted much attention due to their importance as
biologically active compounds (Figure 1),[3] and great
advances have been made in this research area. For
instance, transition-metal-catalyzed meta-selective
C–H arylation of phenols was successfully achieved
Figure 1. Bioactive meta-arylphenol derivatives.
with assistance of rationally designed directing
groups by the Yu group[4] and a traceless directing
1
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10.1002/adsc.201800778
Advanced Synthesis & Catalysis
group by the Larrosa group.[5] In addition, synthesis
of meta-arylphenols by oxidation of the
corresponding cyclohexenones was also extensively
studied since the pioneering work of the Stahl
General conditions: 1a (0.20 mmol), 2a (0.30 mmol),
[Rh(OH)(cod)]2 (5 mol % Rh) in solvent (1.0 mL, and
0.20 mL of H2O was added if used).
[a]
[b]
[c]
[d]
[e]
[f]
Determined by 1H NMR analysis of crude mixture.
Isolated yield of 3a.
group.[6]
These
successes
notwithstanding,
development of new methods for the synthesis of
diversly substituted meta-arylphenols from readily
available reagents under mild conditions is still of
great interest. As part of our continuing interest in the
synthesis of important building blocks under
rhodium(I)-catalysis,[7] herein we report our recent
progress in rhodium-catalyzed arylation of quinone
monoacetal as an alternative approach to para-
methoxyl substituted meta-arylphenols (Scheme 1).
Quinone monoacetal is a type of cyclic dienone
substrate, and it can participate in a conjugate
addition/aromatization process to produce substituted
phenols.[8] Synthesis of arylated phenols by arylation
of quinone monoacetal proved to be feasible,
however, the existing methods are limited to
preparation of ortho-arylphenols via acid-promoted
arylation reactions using electron-rich arenes.[9] We
envisaged that change of the regioselectivity at the
arylation step may furnish valuable meta-
arylphenols.[10] The 1,4-conjugate arylation of
naphthoquinone monoketals with arylboronic acids
was achieved by the Hayashi group,[10b] and we then
speculated that the rhodium(I)-catalyzed arylation
with arylboronic acids[11] may deliver the aryl groups
to the desired position on quinone monoacetal, and a
subsequent aromatization process would furnish
meta-arylphenols (Scheme 1c). However, there are
two major challenges to be considered. First,
conjugate arylation of dienone 1 may lead to a
mixture of mono- and diarylation products.
Furthermore, the rhodium catalyst might not be
compatible with the desired phenol product.[12] With
all these challenges in mind, we embarked on a
project on the synthesis of meta-arylphenols by
KOH (0.20 mmol) was added.
[Rh(OH)(binap)]2 was used as the catalyst.
B(OH)3 (0.20 mmol) was added.
We initiated the investigation by examining the
reaction of quinone monoacetal 1 and phenyl boronic
acid 2a under Rh(I)-catalyzed arylation conditions.
As summarized in Table 1, in the first set of the
experiments, a base was added to prevent possible
deactivation of the rhodium catalyst by the phenol
product.[12] However, none of the desired phenol
product 3a was observed under those basic conditions.
To our surprise, the reaction yielded an unexpected
reductive Heck-type product 5a alongside with the
mono 1,4-conjugate addition product 4a (entries 1 –
3). We then investigated the none basic conditions,
and to our delight, when the reaction was conducted
in anhydrous dioxane without any base, the desired
phenol product 3a was obtained in a moderate yield,
which clearly indicated that the base was not
necessary for this rhodium-catalyzed transformation
(entry 5). A subsequent solvent screening identified
toluene as the best, which furnished 3a as the sole
product in 90% yield (entry 7). Note that the reaction
in other solvents also produced 3a selectively, but the
reaction was slower compared with that in toluene
(entries 6 – 9). Bisphosphine-coordinated rhodium
catalyst could also catalyze the reaction to afford the
desired product selectively, albeit in a diminished
yield (entry 10). The selectivity of 3a over 4a/5a was
dramatic when the reaction conditions were slightly
changed, and we then speculated that 3a might be
formed from 4a/5a under suitable reaction conditions.
Indeed, a mixture of 4a/5a could be converted to
phenol 3a in a high yield with assistance of boric acid
(generated during the Rh-catalyzed arylation reaction
process), while almost no conversion was observed in
the absence of boric acid (eq 1). Being aware of the
importance of boric acid in the formation of 3a, it
was then introduced as an additive to the reaction,
and gratifyingly, the yield of 3a was further improved
to 95% (entry 11).[13]
rhodium(I)-catalyzed
monoacetal.
arylation
of
quinone
Table 1. Rhodium-catalyzed phenylation of quinone
monoacetal 1a.[a]
Entry Solvent
3a:4a:5a[b]
Yield of 3a [%][c]
1
2
3
4
5
6
7
8
dioxane/H2O[d]
0:67:33
0:40:60
0:29:71
0:38:62
66:0:34
100:0:0
100:0:0
100:0:0
100:0:0
100:0:0
100:0:0
--
--
--
dioxane/H2O[d]
dioxane[d]
dioxane/H2O
dioxane
With the success on synthesis of 3a, the generality
of current reaction system was then examined. As
depicted in Scheme 2, diverse arylboronic acids could
be employed in this reaction system, furnishing the
meta-arylphenol products in high yields. Arylboronic
acids bearing electron-donating groups and electron-
withdrawing groups were all well-tolerated (3b – 3e).
In addition, different halogen substitutions at ortho-,
meta-, or para-positions of the arylboronic acids
--
57
70
90
35
71
73
95
THF
toluene
benzene
xylenes
toluene
9
10[e]
11[f]
toluene
2
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10.1002/adsc.201800778
Advanced Synthesis & Catalysis
worked equally well (3f – 3j). Reactions using other
arylboronic acids, such as 1-naphthyl and 2-naphthyl
boronic acids, as well as heteroaryl boronic acids,
also proceeded smoothly to generate the desired
products in high yields (3k – 3n). A gram-scale
synthesis was also carried out to demonstrate the
practicality of current transformation, and 3a could
still be obtained in a high yield when the reaction was
scaled up to 8.0 mmol. However, as a limitation of
current method, some substituted quinone monoacetal
substrates were not able to give the phenol product,
and either simple conjugate addition product (3o) or
low reactivity of substrates was observed.
Scheme 3. Double arylation of quinone monoacetal and
derivatization (For conditions, see Table 1, entry 11).
Based on our experimental results and literature
precedence,[11,14] a plausible convergent reaction
mechanism for the formation of 3 is proposed in
Scheme 4. The arylrhodium species first undergoes a
syn migratory insertion with quinone monoacetal to
form an oxa--allylrhodium intermediate A, which is
assumed to further undergo divergent reaction
pathways (i.e., pathways I and II). Pathway I
proceeds via a classical mechanism: A directly reacts
with arylboronic acid to regenerate arylrhodium
species with concomitant formation of a boron
enolate B.[15] However, pathway II represents an
unprecedented process: A first isomerizes to an
intermediate capable of undergoing syn -hydrogen
elimination, followed by intramolecular hydrogen
transfer (likely via a process involving syn -
hydrogen elimination/dissociation/reinsertion with
less-hindered double bond) to form an oxa--
allylrhodium intermediate C, which then reacts with
arylboronic acid to regenerate the arylrhodium
species and produces a boron enolate D. Boron
enolates B and D then lose one molecular of
methanol under reaction conditions to form the same
intermediate E, which is finally hydrolyzed to afford
the phenol product 3. Products 4a and 5a were
formed under aqueous conditions in the model
reaction, and these results can also be explained by
current mechanism. Product 4a was produced by
hydrolysis of the corresponding intermediate A, while
hydrolysis of intermediate C would generate product
5a. It is noteworthy that the formation of reductive
Heck-type product like 5a via intramolecular
hydrogen transfer is quite rare,[16] and a similar type
of transformation using divinylphosphine oxides as
the substrates was recently disclosed by the Hayashi
group.[17]
Scheme 2. Substrate scope (For conditions, see Table 1,
entry 11).
Phenols bearing two different meta-aryl groups are
also import substructures in bioactive molecules
(Figure 1), but their synthesis often suffers from poor
selectivity and low yield.[3] Gratifyingly, those
molecules are also accessible by current approach
from quinone monoacetal (Scheme 3). The
transformation proceeded through
a
sequential
arylation/quinone monoacetal formation/arylation
process, which involved the formation of a -aryl
quinone monoacetal intermediate. With quinone
monoacetal 1 as the starting material, aryl groups can
be installed stepwise, and doubly meta-arylated
phenol product 6 were produced in moderate to high
yields (6a – 6d). The product 6d can be readily
converted to an analogue of a known LH receptor
antagonist,[3b] which showcased the potential utility of
current study.
3
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10.1002/adsc.201800778
Advanced Synthesis & Catalysis
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Scheme 4. Proposed reaction mechanism.
In summary, we have developed the first selective
synthesis of meta-arylated phenol derivatives from
readily available quinone monoacetal under
rhodium(I) catalysis, which provides an alternative
approach to a class of meta-arylphenol and meta-
diarylated phenol derivatives under mild conditions.
In addition, an unprecedented convergent reaction
pathway was involved in the formation of the final
product, and the novel transformation for generating
the reductive Heck-type product 5a may inspire the
discovery of other interesting reactions, which is
currently under investigation in our laboratory.
Experimental Section
General Procedure for the Rhodium-Catalyzed Formal
Arylation/Demethoxylation of Quinone Monoacetal
[Rh(OH)(cod)]2 (2.3 mg, 5 mol % Rh), boric acid (12.4 mg,
0.20 mmol), and arylboronic acid (0.30 mmol) were placed
in an oven-dried Schlenk tube under nitrogen. Quinone
monoacetal (0.20 mmol) and anhydrous toluene (1.0 mL)
was then added and the resulting mixture was stirred at 60
oC. After 5 hours, the reaction was diluted with EA (5 mL)
and water (5 mL). The layers were separated and the
aqueous layer was extracted again with EA (5 mL). The
organic layers were combined and filtered through a short
pad of silica gel with EtOAc as eluent. The solvent was
removed on a rotary evaporator, and the residue was
purified by silica gel chromatography eluting with
petroleum ether/ethyl acetate (10/1) to give the product 3.
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We are grateful for the generous financial support from the
National Natural Science Foundation of China (21602253), the
Natural Science Foundation of Jiangsu Province (BK20160749),
and the Six Talent Peaks Plan of Jiangsu Province.
4
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10.1002/adsc.201800778
Advanced Synthesis & Catalysis
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5
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10.1002/adsc.201800778
Advanced Synthesis & Catalysis
COMMUNICATION
Synthesis of meta-Arylated Phenol Derivatives by
Rhodium(I)-Catalyzed Arylation of Quinone
Monoacetal
Adv. Synth. Catal. Year, Volume, Page – Page
Jianhang Huang, Na Liu, Tao Lu,* and Xiaowei
Dou*
6
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