Pd-catalyzed direct arylation of electron-deficient polyfluoroarenes with aryliodine(III) diacetates

Article abstract of DOI:10.1016/j.tetlet.2014.11.033

A Pd-catalyzed direct arylation of electron-deficient polyfluoroarenes with readily available aryliodine(III) diacetates was developed with moderate to good yields. The process exhibited good functional tolerance with respect to methyl, methoxy, bromo, chloro, trifluoromethyl, cyano, and aldehyde groups. Mechanistic studies revealed this coupling involved in situ generation of aryl iodide from heating-promoted decomposition of aryliodine(III) diacetate, followed by coupling with polyfluoroarenes substrates to afford the desired products.

Full text of DOI:10.1016/j.tetlet.2014.11.033

Tetrahedron Letters 56 (2015) 123–126
Contents lists available at ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Pd-catalyzed direct arylation of electron-deficient polyfluoroarenes
with aryliodine(III) diacetates
⇑
⇑
Zhengjiang Fu , Qiheng Xiong, Wenbiao Zhang, Zhaojie Li, Hu Cai
College of Chemistry, Nanchang University, Nanchang, Jiangxi 330031, China
a r t i c l e i n f o
a b s t r a c t
Article history:
A Pd-catalyzed direct arylation of electron-deficient polyfluoroarenes with readily available arylio-
dine(III) diacetates was developed with moderate to good yields. The process exhibited good functional
tolerance with respect to methyl, methoxy, bromo, chloro, trifluoromethyl, cyano, and aldehyde groups.
Mechanistic studies revealed this coupling involved in situ generation of aryl iodide from heating-
promoted decomposition of aryliodine(III) diacetate, followed by coupling with polyfluoroarenes
substrates to afford the desired products.
Received 19 August 2014
Revised 23 October 2014
Accepted 9 November 2014
Available online 15 November 2014
Keywords:
Pd
Ó 2014 Elsevier Ltd. All rights reserved.
Arylation
Polyfluoroarene
C–H activation
For environmental and economical attractiveness, transition-
metal-catalyzed direct arylation of aromatic C–H bonds has been
a powerful tool for straightforward synthesis of valuable biaryl
products from a large pool of arenes over the last decades, which
usually performs a practical alternative route to the traditional
cross-coupling reactions and becomes the focus of many research
activities.1 Of these reactions, electron-deficient polyfluoroarenes
are extensively employed in a wide range of areas to prepare cor-
responding polyfluorobiaryl structural motif, ranging from the
elaboration of pharmaceutical chemistry to materials science.2,3
In this regard, some initial works include the Pd-catalyzed selec-
tive C–H bond arylation of electron-deficient polyfluoroarenes
with aryl halides to synthesis of fluorobiaryl or heterocycle-con-
taining biaryl molecules,4 and further effort made by Daugulis
led to the development of Cu-catalyzed direct arylation of polyflu-
oroarenes via C–H bond activation with aryl halides.5 Su and others
established oxidative C–H arylation of polyfluoroarenes with
arylboronic acids,6 organosilicon reagents,7 and arenediazonium
tetrafluoroborates,8 respectively. However, some of the coupling
partners in these reported transformations often suffer from limi-
tations for disadvantage with regard to the use of unstable or hard
to prepare organometallic reagents. In addition, elegant works in
oxidative cross-coupling of polyfluoroarenes via C–H bond activa-
tion with alkenes,9 alkynes,10 (hetero)arenes,11 aromatic carboxylic
acids,12 amines,13 and sulfoximines14 has been reported. Among
these reported reactions, polyfluorobiaryls can be successfully
obtained from new methodologies via oxidative cross-coupling of
electron deficient polyfluoroarenes with C–H activation of
(hetero)arenes11 or decarboxylation of aromatic carboxylic acids.12
In contrast to arylation reactions of polyfluoroaromatic C–H bond
with (hetero)arenes or aromatic carboxylic acids as aryl source that
have recently been attracted great attentions, nevertheless, to the
best of our knowledge, no example of the direct C–H bond
functionalization of electron-deficient polyfluoroarenes with
aryliodine(III) diacetates as aryl source has been revealed.
Phenyliodine(III) diacetate is one of the most useful hypervalent
iodine reagents, Kitamura reported an easy and cheap procedure to
synthesize (diacetoxyiodo)arenes by the reaction of arenes with
iodine under mild conditions (Ar-H + I2).15 Therefore, basing on
its readily availability and rich chemistry,16–18 phenyliodine(III)
diacetate is widely used in considerable organic synthesis, it is
not only served as a surrogate for oxidant in oxidative transforma-
tions,17 but applied for radical reactions to generate oxygen-cen-
tered radicals and carbon-centered radicals with potential
utility.18 Furthermore, although apparent progress has been made
on transition-metal-mediated coupling reactions between diaryli-
odonium salts as the arylation reagent and arene,19 phenol ester,20
alkene21 and various nucleophiles,22 the employment of arylio-
dine(III) diacetate as the arylation or acetoxylation reagents in
the oxidative transformations also received considerable atten-
tions,23 for example, efforts made by Mao23a and Magedov23b have
led to the development of palladium-catalyzed arylation of alkenes
with aryliodine(III) diacetate; Suna23c and others23d–f disclosed
Pd-catalyzed acetoxylation of (hetero)arenes or olefins with the
employment of aryliodine(III) diacetate. Recently, the group of
⇑
Corresponding authors.
E-mail addresses: fuzhengjiang@ncu.edu.cn (Z. Fu), caihu@ncu.edu.cn (H. Cai).
http://dx.doi.org/10.1016/j.tetlet.2014.11.033
0040-4039/Ó 2014 Elsevier Ltd. All rights reserved.

124
Z. Fu et al. / Tetrahedron Letters 56 (2015) 123–126
Cheng24a and Fairlamb24b reported direct arylation of benzoxazole
C–H bonds with aryliodine(III) diacetate. With particular interest
in the transformation reaction of electron-deficient arene C–H
bond, we describe that such an attempt to use ArI(OAc)2 reagents
in an oxidative electron-deficient polyfluoroarene C–H bond
transformation resulted in the direct arylation reaction of elec-
tron-deficient polyfluoroarene with Pd/Ag bimetallic system, and
this observation represents a beneficial complement to the well
documented versions of direct arylation reaction of electron-
deficient polyfluoroarenes.
(entry 14). The effect of different loading of Ag2CO3 was the next
variable evaluated, decreasing the amount of Ag2CO3 to 1.5 equiv
gave comparable yield (75%), however, further reducing Ag2CO3
loading to 1 equiv led to a slightly lower yield (70%) (entries 15
and 16). Varying the ratio of DMSO to DMF in the mixed solvents
system led to change in the yield, as a result, replacing 5%
DMSO–DMF with 2.5% DMSO–DMF depressed the yield (entry
17). The influence of reaction temperature on the catalytic process
was also investigated, studies showed that lowering reaction tem-
perature to 110 °C did not affect the efficiency (74%), whereas
unsatisfied yield (64%) was obtained when reaction conducted at
90 °C (entries 18–19). Reaction time also had significant effect on
this reaction, and a shorter reaction time did not contribute to
increasing the yield (entry 20).
After identifying the factors influencing the reaction outcome,
the scope of this protocol with respect to polyfluoroarene was
explored by employing the conditions of entry 18 in Table 1. As
shown in Table 2, beside the pentafluorobenzene, a broad array
of polyfluoroarenes, tetrafluoro-, trifluoro-, and even some poly-
chloroarenes were chemoselectively arylated with (diacetoxy-
iodo)benzene 2a under the standard conditions to furnish
corresponding products in moderate to good yields. Electron-rich
substituents such as methyl and methoxy, electron-deficient
substituents such as bromo, trifluoromethyl, cyano, and aldehyde
groups all could be quite well tolerated, and it was observed that
the reaction was facilitated when a substituent at the para-position
of tetrafluorobenzene derivative has electron-donating effect or
p–pi conjugation effect (3a–d), on the contrary, the reaction was
undermined when an electron-withdrawing group at the
para-position of tetrafluorobenzene derivative (3e–g). 1,2,3,5-tet-
rafluorobenzene and 1,2,4,5-tetrafluorobenzene, each of which
possesses two potential reaction sites, generated mixtures of
mono- and di-substituted arylation products (3i and 3i0, 3j and
3j0) in 62% and 57% overall yield, respectively. Interestingly, aryla-
tion of pentachlorobenzene was also achieved (3h), the low yield
suggested that a C–H bond flanked with chlorine atoms was less
We initiated our investigation by taking reaction of pentaflu-
orobenzene 1a with iodobenzene diacetate 2a as the model
reaction for the optimization studies. Table 1 presents some
selected results from these optimization studies that showed the
effects of the solvent, base, and other factors on the reaction out-
come. At first, using a stoichiometric K3PO4 as base in the model
reaction in DMF solvent, it was found that the catalyst greatly
affects reaction efficiency, the reaction of 1a with 2a conducted
in the presence of 10 mol % Pd(OAc)2 as catalyst under nitrogen
atmosphere furnished desired product 2,3,4,5,6-pentafluorobiphe-
nyl 3a in 54% isolated yield in DMF at 130 °C (entry 3, Table 1),
however, either inferior yield (23%) displayed when 20 mol % CuI
instead of 10 mol % Pd(OAc)2 or no product was obtained when
Pd catalyst was absent (entries 1–2), the results indicated that Pd
catalyst has an essential role in the catalytic reaction. Subse-
quently, a brief survey of the solvents under otherwise identical
conditions, including polar and less polar solvents, revealed that
better yields could be obtained in polar solvents than that in less
polar solvent such as toluene (entries 4–9). Considering DMSO
could play an important role and function as a ligand to activate
the Pd catalyst and prevent the formation of palladium
black,11c,24b,25 thus, different bases were screened in the model
reaction in 5% DMSO/DMF (v/v) mixed solvents (entries 10–14).
Among them, K3PO4, KOAc, KOtBu, K2CO3, LiOtBu, and Ag2CO3
appeared to be the best choice and had a significant influence on
the reaction, delivering 3a in synthetically useful levels (76% yield)
Table 1
Selected results of screening the optimal conditionsa
F
F
F
F
F
F
F
F
catalyst
base, ligand, additive
F
PhI(OAc)2
+
F
temp, solvent
20 h
1a
2a
3a
Entry
Catalyst (mol %)
Base (equiv)
Temp. (°C)
Solvent
Isolated yield (%)
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20b
—
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
K3PO4 (2)
KOAc (2)
130
130
130
130
130
130
130
130
130
130
130
130
130
130
130
130
130
110
90
DMF
DMF
DMF
DMSO
NMP
CH3CN
THF
Toluene
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
2.5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
5% DMSO–DMF
0
23
54
37
36
24
20
<5
39
43
40
<5
35
76
75
70
69
74
64
66
CuI (20)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
Pd(OAc)2 (10)
KOtBu (2)
K2CO3 (2)
LiOtBu (2)
Ag2CO3 (2)
Ag2CO3 (1.5)
Ag2CO3 (1)
Ag2CO3 (1.5)
Ag2CO3 (1.5)
Ag2CO3 (1.5)
Ag2CO3 (1.5)
110
a
Conditions: 1a (0.2 mmol), 2a (1.2 equiv), solvent (2 mL), 20 h.
Reaction run for 10 h.
b

Z. Fu et al. / Tetrahedron Letters 56 (2015) 123–126
125
Table 2
Pd-catalyzed direct arylation of polyfluoroarenes with iodobenzene diacetatea
Scheme 1. Two assumed mechanisms of the transformation.
Table 3
Pd-catalyzed direct arylation of pentafluorobenzene with (diacetoxyiodo)benzene
derivativesa
a
Reaction conditions: polyfluoroarene
1 (0.2 mmol), 2a (1.2 equiv), Pd(OAc)2
(10 mol %), Ag2CO3 (1.5 equiv), 5% DMSO–DMF (2 mL), 110 °C, 20 h.
b 1 mmol scale.
c Reaction conducted at 130 °C.
reactive probably due to its decreased acidity. Heteroaromatic
compounds proved to be suitable substrates, regardless of the
presence of fluoro or chloro substituent on the pyridine ring
(3k, 3l, and 3m), albeit in moderate yields for tetrafluoropyridine
(3k and 3l) under a slightly elevated temperature. Notably,
1-bromo-2,3,5,6-tetrafluorobenzene, pentachlorobenzene, and tet-
rachloropyridine formed the hoped-for products (3d, 3h, and 3m)
with the halogen moieties (–Br, Cl) remaining intact, which could
be used for installing other functional groups via the transforma-
tions of the C–Hal bonds, providing the potential application of
this methodology. This reaction can be scaled up, for example, as
illustrated by the reaction on 1 mmol scale that offered an equal
yield (74%) comparable to that on 0.2 mmol scale (3a, Scheme 1).
Using Kitamura’s method (Ar-H + I2),15 (diacetoxyiodo)benzene
derivatives 4a–c were prepared from corresponding arene under
mild conditions. Subsequently, the direct arylation coupling of
(diacetoxyiodo)benzene derivatives with pentafluorobenzene 1a
was also investigated under standard conditions. The results are
summarized in Table 3, (diacetoxyiodo)benzene derivatives bear-
ing methyl, bromo, and chloro groups served as arylating reagents
for the direct arylation of pentafluorobenzene and proceeded with
quantitative conversion. The phenyl core of ArI(OAc)2 bearing elec-
tron-donating group gave moderate yield (4a), whereas bearing
electron-withdrawing groups furnished good yields, for example,
satisfied yields were gave when p-halogen (Br, Cl) substitution
on the phenyl ring of (diacetoxyiodo)benzene (4b–c).
a
Reaction conditions: Pentafluoroarene 1a (0.2 mmol), 2 (1.2 equiv), Pd(OAc)2
(10 mol %), Ag2CO3 (1.5 equiv), 5% DMSO-DMF (2 mL), 110 °C, 20 h.
Moreover, the reaction of pentafluorobenzene 1a with this freshly
generated iodobenzene under the standard reaction conditions
was analyzed by 1H NMR and got indication of stoichiometric con-
version into desired product 3a. Although the reaction between
polyfluoroarenes and iodobenzene was reported by Fagnou and
others,4a,4b,4d however, the reaction of polyfluoroarenes with
(diacetoxyiodo)arenes provides an indirect method to produce
polyfluorobiaryls via the coupling of electron-deficient polyfluoro-
arenes with arenes.
Consequently, two different Pd(II)/Pd(IV) mechanisms were
assumed for this arylation of pentafluorobenzene with iodoben-
zene diacetate.6,24a As illustrated in Scheme 1, Cycle A involves
the initial formation of aryl-Pd(IV) species III via the oxidative
addition of the in situ generated iodobenzene to original Pd(II), fol-
lowed by the palladation of pentafluorobenzene via concerted
metalation–deprotonation4a and subsequent reductive elimina-
tion. Cycle B begins with the formation of pentafluorophenyl-Pd(II)
species I via the activation of the C–H bond of pentafluorobenzene,
followed by the oxidative addition of the in situ generated iodo-
benzene to pentafluorophenyl-Pd(II) species and then reductive
elimination. In this regard, multiple roles were assigned to Ag2CO3
as the base and promoter in transformation. Considering the oxida-
tive addition of the in-situ generated iodobenzene to original Pd(II)
is easier than that to pentafluorophenyl-Pd(II) species I, thus, the
reaction is possible to favor Cycle A as the catalytic cycle in this
transformation.
Some observations were performed to gain some insights into
the reaction mechanism. Firstly, GC–MS and NMR spectroscopic
analysis revealed that iodobenzene was produced when heating
compound 2a with 1 equiv of Ag2CO3 in 5% DMSO–DMF under
nitrogen at 110 °C for 2 h, this result is consistent with the
literature reported by Fairlamb and co-workers very recently.24b

126
Z. Fu et al. / Tetrahedron Letters 56 (2015) 123–126
6. Wei, Y.; Kan, J.; Wang, M.; Su, W.; Hong, M. Org. Lett. 2009, 11, 3346.
In summary, we have established a new Pd-catalyzed method
7. Fan, H.; Shang, Y.; Su, W. Eur. J. Org. Chem. 2014, 3323.
for direct arylation of various electron-deficient polyfluoroarenes
featuring the use of inexpensive and readily available arylio-
dine(III) diacetates as the aryl source. Preliminary mechanistic
studies disclosed that this reaction involved in situ generation of
aryl iodide from the heating of aryliodine diacetate in the presence
of a base, followed by coupling of polyfluoroarene to give the target
product. The characteristics of good functional group tolerance and
yields provide the described procedure with a broad utility in
organic synthesis. Efforts are currently underway to improve the
efficiency of this reaction further and investigate the mechanism
more detailedly.
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Acknowledgments
We gratefully acknowledge the financial support of the National
Natural Science Foundation of China (NSFC) (21301088 and
21162015), the National Key Basic Research Program of MOST of
China (2012CBA01204), the Natural Science Foundation of Jiangxi
Province (20142BAB213001) and Science Foundation of State Key
Laboratory of Structural Chemistry (20100009).
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Supplementary data
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.tetlet.2014.
11.033.
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