Regioselective Oxidative Arylation of Fluorophenols

Article abstract of DOI:10.1002/anie.201910352

A metal free and highly regioselective oxidative arylation reaction of fluorophenols is described. The relative position of the fluoride leaving group (i.e., ortho or para) controls the 1,2 or 1,4 nature of the arylated quinone product, lending versatilit

Full text of DOI:10.1002/anie.201910352

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Accepted Article
Title: Regioselective oxidative arylation of fluorophenols
Authors: Congjun Yu and Frederic William Patureau
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Regioselective oxidative arylation of fluorophenols
[a]
[a]
Congjun Yu, and Frederic W. Patureau*
In memory of our colleague, Prof. Dieter Enders (1946-2019)
[
12]
Abstract: A metal free and highly regioselective oxidative arylation
reaction of fluorophenols is described. The relative position of the
fluoride leaving group (ie ortho or para) controls the 1,2 or 1,4 nature
of the arylated quinone product, lending versatility and generality to
this oxidative, defluorinative, arylation concept.
and catalysts were developed to achieve this reaction.
Nevertheless, these methods are typically not regioselective.
Indeed, the presence of a single R functional group at the
quinone core generates three inequivalent but similarly reactive
electrophilic positions, usually leading to regioisomeric mixtures
of diversely arylated coupling products. Cross dehydrogenative
1
coupling (CDC) approaches were also developed with
The quinone motif is ubiquitous in chemistry, material science,
[13]
success,
for example by You and co-workers. Nevertheless,
[
1]
nanotechnology, and medicine. Due to their electron and
hydrogen transport properties, quinone derivatives participate in
these modern methods, while highly step and atom economical,
do not solve any further the regioselectivity problem at the
quinone. Herein, we propose to solve this problem for the 1,4
and the more challenging 1,2 quinones (Scheme 1).
[2]
various biological activities. For example, they act as mem-
[
3]
brane-bound compounds found in many living organism, and
[
4]
play a key role in cell respiration. In addition, they are
[
5]
[6]
embedded in many natural products, drugs, and materials.
Among them, arylated quinones are particularly important
Figure 1). In material chemistry, they possess unique
photochemical and electronic properties that make them useful
(
[7]
in photosynthesis, as well as appealing structures for the dye
[
8]
industry.
Thus, the efficient synthesis of aryl substituted
quinones remains a strategic objective, especially in terms of
arylation regioselectivity, a largely unaddressed challenge.
Figure 1. Natural products containing arylated quinones.
Scheme 1. Synthesis of arylated quinones.
Some traditional methods to synthesize arylated quinones
include pre-halogenation of the quinone core followed by a
[
9]
palladium-catalyzed cross-coupling, or utilizing diazonium salts
Since a few years, our research team has been focused on the
[
10]
[
14]
as the aryl radical sources to functionalize the quinone.
The
development of new oxidant mediated CDCs.
Indeed, the
latter methods however are neither step nor atom economical,
and typically rely on sensitive/onerous palladium/phosphine
nature of the oxidant is particularly important in the context of
CDCs because of its specific interactions with the substrates
[
11]
catalysts. In 2011, Baran et al.
ideal radical sources to react with quinones in the presence of
catalytic amounts of AgNO . Since then, several radical sources
reported boronic acids to be
(
and catalysts). Therefore, tuning its design can alter reactivity,
and thus in some cases lead to new reaction concepts. Along
this strategy, we were attempting to develop cross
3
a
dehydrogenative arylation method of phenols with notably
hypervalent iodine oxidants, when we serendipitously came
across the very regioselective arylated quinone 1c depicted in
Scheme 2. We then optimized the reaction conditions. It rapidly
transpired that the reaction only operates with fluorophenols,
wherein the fluoride is a leaving group.
[
a]
M. Sc. C. Yu, Prof. Dr. Frederic W. Patureau
Institute of Organic Chemistry, RWTH Aachen University,
Landoltweg 1, 52074 Aachen, Germany
E-mail: frederic.patureau@rwth-aachen.de
Supporting information for this article is given via a link at the end of
the document.
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is replaced by chloride, bromide, or nitro. Furthermore, neither
quinones nor hydroquinones deliver any arylation products,
indicating that the latter structures are not reaction intermediates.
In other words, the remote fluoride anion leaving group plays an
essential enabling role in this arylation reaction. Different
[
15]
hypervalent iodine oxidants
were otherwise tested in this
reaction. Iodosodilactone (I-8), a rare but trivial (non-fluorinated)
hypervalent iodine reagent, performed best (80% yield of test
coupling product 1c). Iodosodilactone I-8 was firstly synthesized
[
16]
and reported by Agosta
in 1965. However, almost no
reactions enabled by this iodine reagent were reported since
[
17]
then. In 2012, the Zhang group
reported the single crystal
structure of iodosodilactone I-8, showing an unusual planar
3
shape which is unlike other typical aryl-λ -iodanes (ie PIDA),
with a typical T-shape structure. In any case, iodosodilactone I-8
can be prepared in large amount with high yield. Iodosodilactone
I-8 is quite stable, it is neither air nor moisture sensitive, and can
be stored for several months at room temperature without any
detectable decomposition. Interestingly, the solvent has also a
large impact on the reaction outcome. 1-Nitropropane, a cheap
but also relatively rarely utilized solvent, outperforms other
nitroalkanes and diverse usual organic solvents such as 1,2-
dichloroethane (DCE). With the best conditions in hand, we then
explored the scope of this metal-free arylation reaction, for the
synthesis of a variety of arylated 1,4-quniones (Scheme 3). For
all the examples in which a para-fluorophenol was utilized as
one of the building blocks, the arylation occurred exclusively at
the 6-C―H-position. No 5-C―H arylation, nor ipso-(4-C―F)-
arylations were detected. Electron rich arylation coupling
partners were found to be important in this reaction, anisoles
reacting particularly well. It should moreover be noted that the
C―H regioselectivity on the side of the anisole coupling partner
is usually high, even if in some cases some minor (o/m/p)
isomers could be detected.
1
Scheme 2. Reaction optimization, yields determined by H NMR analysis of
the crude reaction mixture with 1,3,5-trimethoxybenzene as an internal
standard.
Moreover, the ipso arylation event does not occur. Instead, the
arylation consistently occurs in meta position with respect to the
fluoride leaving group (in the case of para-fluorophenols starting
materials, see beneath for ortho-fluorophenols). Importantly, the
arylation product is not observed when the fluoride leaving group
Scheme 3. Regioselective synthesis of arylated 1,4-quinones, isolated yields. [a] Trace amounts of different selectivities (o/m/p) at the anisole moiety. [b]
Iodosobenzene diacetate (PIDA, I-1) was utilized instead of iodosodilactone.
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Some interesting functional groups were otherwise well tolerated,
such as halides (5c, 11c, 16c, 20c), an allyl ether (4c), an
isoxazole heterocycle (18c), and even phenols (19-21c). In the
latter cases, very important phenolic quinones could be
constructed in a single step, which would be difficult to
synthetize otherwise (for the relevance of such phenolic quinone
structures, see for example Euonyquinone A, Figure 1). In
addition to arylated 1,4-quinone products, arylated 1,2-quinones
could be accessed as well, from ortho-fluorophenols substrates
(
Scheme 4). 1,2-Quinones are also ubiquitous in many natural
[18]
products, drugs and materials.
However, the regioselective
[
19]
arylation of 1,2-quinones is very challenging proposition.
Interestingly, in this configuration, the ortho-fluorophenol building
block must also carry para-methoxy electron donating
a
functional group. Moreover, the arylation regioselectivity has
now changed from meta to para C―H arylation with respect to
the fluoride leaving group, thus delivering 4,5-disubstituted-1,2-
quinones. While the isolated yields remain moderate (1e-9e), a
large variety of anisole arylation coupling partners were well
tolerated. In spite of the mentioned limitations above, the
operational simplicity of this approach may pave the way for
future arylation methods of 1,2-quinones. Finally, we also
explored and optimized a diarylation method derived from these
Scheme 5. Regioselective synthesis of diarylated 1,4-quinones, isolated yields.
[
a] Trace amounts of different selectivities (o/m/p) at the anisole moiety.
[
20]
reaction conditions, with a single fluoride leaving group.
Re-
optimizing the hypervalent iodine oxidant (PIFA, I-2) as well as
the reaction temperature (-20°C) afforded 2,6-diarylated-1,4-
quinones in promising yields (Scheme 5).
This gives an indication as to the role and fate of the fluoride
leaving group. Indeed, based on this observation, we propose
[
23]
[24-26]
that “pseudo-ketal” intermediate int-II
is formed (Scheme
6, mechanistic proposal). The fluoride anion would then attack
the adjacent carboxyl ester upon the remote nucleophilic attack
of the arene coupling partner (intermediates int-III and int-IV).
This would thereby release the oxygen atom towards the
hydroquinone intermediate int-V, which would further oxidize
under aerobic conditions to the final 1,4-quinone coupling
product c. In support of this hypothesis, we furthermore noted
that while the reaction still operates under carefully degassed
condition (N
only 23% (see SI). Thus, these combined elements: 1) presence
of AcF, and 2) reaction operating under N , arguably constitute
2
), the isolated yield of product 1c then decreases to
2
solid evidence that the second oxygen atom does indeed come
from the hypervalent iodine oxidant. In the case of ortho-
fluorophenol building blocks, the corresponding reaction
intermediate int-V’ is in principle blocked at the quaternary
carbon stage. We propose that this structure is unlocked by the
1,2-aryl migration to the neighboring most electrophilic carbon,
yielding catechol intermediate int-VI’ / int-VII’, in turn oxidized
under aerobic condition to the 1,2 quinone final coupling product
e. Importantly, when meta- fluorophenol (h) was engaged as a
Scheme 4. Regioselective synthesis of arylated 1,2-quinones, isolated yields.
[
a] Trace amounts of different selectivities (o/m/p) at the anisole moiety.
substrate
with
either
anisole
or
alternatively
1,4-
dimethoxybenzene, no coupling products were found. Finally,
we propose the double arlyation products g of Scheme 5 to arise
from a simple Brønsted acid catalyzed second arylation event
(intermediate int-V’’), followed by aerobic oxidation. This is in
good agreement with the fact that the more electrophilic / acidic
hypervalent iodine reagent I-2 performs particularly well in this
double arylation method (Scheme 5 & 6). Moreover, it should be
noted that in the absence of a second fluoride leaving group, the
regioselectivity of this second arylation event is probably
controlled by the steric impact of the first aryl group in
combination with a very low reaction temperature (-20 °C).
Some mechanistic experiments were then performed. Firstly, a
1
9
F NMR in situ measurement in a polytetrafluoroethylene
PTFE) tube was carried out. I-1 (PIDA) was utilized as the
oxidant in this experiment, under otherwise standard conditions,
(
1
9
and the F NMR spectra were measured every 30 minutes after
the reaction started. The rapid appearance of a characteristic
3
quartet NMR signal was observed at around δ= +49 ppm (q, JF-
[
21]
H
= 7 Hz), calibrated in relation to benzotrifluoride (-63 ppm),
increasing in time, which corresponds to the buildup of acetyl
fluoride (AcF, see SI).
[22]
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anticipate that this method will impact the field of bioactive and
material based quinones.
Acknowledgements
ERC project 716136: “2O2ACTIVATION” is gratefully
acknowledged for financial support.
Keywords: Regioselective arylation • Hypervalent iodine • CDC
•
Arylated quinone • fluorophenols
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In summary, we have developed a regioselective oxidative
arylation method of fluorophenols. The method directly provides
highly regioselective arylated para and even ortho quinones, in
contrast to the state of the art in this field. This high
regioselectivity is dictated by the relative position of the fluoride
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Entry for the Table of Contents
Layout 1:
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F trick: A metal free and highly
regioselective oxidative arylation
reaction of fluorophenols is described.
Congjun Yu, Frederic W. Patureau*
Page No. – Page No.
Regioselective oxidative arylation of
fluorophenols
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