Ni-Catalyzed C?F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles

Article abstract of DOI:10.1002/adsc.201701506

A Ni-catalyzed C?F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)₂/IMes catalytic system.

Full text of DOI:10.1002/adsc.201701506

Title: Ni-Catalyzed C–F Bond Functionalization of Unactivated Aryl
Fluorides and Corresponding Coupling with Oxazoles
Authors: Youzhi Yin, Xiaoyu Yue, Qi Zhong, Hanmin Jiang, Ruopeng
Bai, Yu Lan, and Hua Zhang
This manuscript has been accepted after peer review and appears as an
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201701506
Link to VoR: http://dx.doi.org/10.1002/adsc.201701506

Advanced Synthesis & Catalysis
10.1002/adsc.201701506
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Ni-Catalyzed C–F Bond Functionalization of Unactivated Aryl
Fluorides and Corresponding Coupling with Oxazoles
+
a
+b
a
a
b,
b,
Youzhi Yin, Xiaoyu Yue, Qi Zhong, Hanmin Jiang, Ruopeng Bai, * Yu Lan, *
a,
and Hua Zhang *
a
College of Chemistry, Nanchang University, 999 Xuefu Avenue, Nanchang 330031, P. R. China. Email:
huazhang@ncu.edu.cn
b
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, P. R. China. Email:
ruopeng@cqu.edu.cn; lanyu@cqu.edu.cn
These authors contributed equally to this work.
+
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######.((Please
delete if not appropriate))
Abstract. A Ni-catalyzed C–F bond functionalization of other carbon-heteroatom bond formations[9] have
unactivated aryl fluorides with oxazoles as coupling been reported as well (Scheme 1). Although
partners was developed. Various arylated oxazoles could be significant progress has been made in the
[10]
obtained in moderate to good yields in the presence of development of aromatic C–H bond arylation, rare
Ni(cod)
2
/IMes catalytic system. A rapid synthesis of natural examples have been reported on directly coupling
[11]
product texaline was also demonstrated using this protocol.
This transformation could be potentially utilized in
regioselective introduction of an oxazole group in late-
stage synthetic applications.
both C–F and C–H bonds.
Herein, we
communicate Ni-catalyzed C–F/C–H cross-
a
coupling involving the C–F bond cleavage of
unactivated aryl fluorides and C–H bond
functionalization of oxazoles (Scheme 1). This novel
C–F/C–H coupling would offer a new strategy for the
synthesis of complex 2-aryl oxazole derivatives
wherein the fluoro group could be utilized as an
Keywords: nickel catalysis; C–F functionalization; C–H
functionalization; oxazoles; cross-coupling
[12]
oxazole equivalent.
Fluorine-containing organic compounds are widely
found in a broad range of areas such as medicine,
[1]
biochemistry, catalysis, material science, etc. In the
past decade, great efforts have been devoted to
developing protocols that could efficiently construct
carbon-fluorine (C–F) bond.[2] In light of the growing
importance of C–F bond formation, C–F bond
functionalization has also attracted a great deal of
interest.[ The availability of fluoroarenes has been
significantly expanded with the recent advances in
fluorination methods while the inert nature of C–F
bond makes C–F bond functionalization a useful
protocol in the late-stage synthesis of complex
organic compounds.
3]
Scheme 1. Catalytic C–F/C–H coupling.
We began by investigating the arylation of
benzoxazole 1a with 4-fluoro-1,1'-biphenyl 2a in the
presence of nickel catalyst. After extensive screening,
the best result was obtained when the reaction was
Owing to the fact that C–F bond is a strong and
inert chemical bond in organic compounds, carbon-
carbon and carbon-heteroatom bond formation via C–
F bond cleavage is always challenging. Since the
conducted under the conditions consisting of Ni(cod) ,
2
IMes•HCl
(1,3-bis(2,4,6-trimethylphenyl)
t c
imidazolium chloride) and NaO Bu in hexane at 160
pioneering work on the Kumada-Corriu cross-
o
coupling involving aryl fluorides,[
4]
various
C for 16 h affording the arylated product 3a in 87%
GC yield and 80% isolated yield (Table 1).
transition-metal-catalyzed cross-coupling reactions
involving aryl fluorides and stoichiometric
organometallic r5e]agents have been developed
The effect of alteration to the “standard conditions”
is listed in Table 1. Nickel catalyst is essential for this
1).[
Additionally,
catalytic
reaction as no arylation occurred without Ni(cod) .
2
(
Scheme
hydrodefluorination, borylation, silylation,[8] and
[
6]
[7]
The use of Ni(acac)
2
and NiCl as catalyst precursors
2
resulted in few or no products indicating that Ni(0)
1
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Advanced Synthesis & Catalysis
10.1002/adsc.201701506
species might be required to initiate the reaction. Low
methyl group in meta and para position afforded the
corresponding arylated products 3g and 3h in 74%
and 61% yield, respectively. In general, substrates
bearing both electron-donating substituents (3j, 3k)
and electron-withdrawing substituents (3l) worked
well under the standard conditions. Amide group
could also be tolerated under standard conditions.
Unfortunately, halogen groups like chloride and base
sensitive groups like ester and aldehyde could not be
tolerated. To our delight, heteroaryl fluoride 2n could
also react well to form the biaryl product in 64%
yield. Furthermore, other heteroarenes were tested for
this C–H arylation as well. Substituted benzoxazoles
and oxazoles were also suitable substrates giving the
desired products in moderate yields. Other azoles and
acidic arenes like polyfluoroarenes were tested, in
which only N-Me benzimidazole afforded trace
product while other azoles and polyfluoroarenes gave
no product.
yield of 3a was obtained with the rest 2a recovered
when 10 mol% Ni(cod) was employed. Elongation
2
of reaction time gave similar result suggesting the
deactivation of nickel catalyst. Both N-heterocyclic
carbene ligands and phosphine ligands showed
efficiency for this transformation, although these
ligands (IPr•HCl, ICy•HCl, PPh
3
, PCy ) were found
3
to be less effective. As to the base effect, other
t
alkaline metal alkoxides like KO Bu led to low yield
while K
3
PO
4
and Cs
2
CO afforded no product. This
3
arylation occurred smoothly in non-polar solvents
such as toluene (70% yield) while no product was
obtained using other solvents like DMF or DME. Due
to the strong and inert nature of C–F bond, lowering
the reaction temperature led to decreased yield.
Table 1. Ni-catalyzed C–H arylation of 1a with 2a: effects
of reaction parameters.
Table 2. Ni-catalytic C–F/C–H coupling of unactivated
a,b
aryl fluorides with oxazoles.
Entry Variation from “standard conditions”a Yield[%]b
1
2
3
4
none
No Ni(cod)
Ni(acac)
NiCl , instead of Ni(cod)
10 mol% Ni(cod)
10 mol% Ni(cod)
IPrHCl, instead of IMesHCl
ICyHCl, instead of IMesHCl
87(80)c
0
18
0
39
42
64
9
12
57
29
0
2
2
, instead of Ni(cod)
2
2
2
d
5
6
2
2
e
7
8
9
PPh , instead of IMesHCl
3
1
0
1
2
3
4
5
6
7
PCy , instead of IMesHCl
3
t
t
1
1
1
1
1
1
1
KO Bu, instead of NaO Bu
t
K
3
PO
4
, instead of NaO Bu
, instead of NaO Bu
t
Cs CO
2
3
0
70
0
0
73
c
Toluene, instead of hexane
DME, instead of hexane
c
c
DMF, instead of hexane
o
o
140 C, instead of 160 C
a)
Standard reaction conditions: 1a (0.4 mmol), 2a (0.2
mmol), Ni(cod) (0.04 mmol), IMes•HCl (0.08 mmol),
2
t
c
o
b)
NaO Bu (0.6 mmol), hexane (1.0 mL), 160 C, 16 h. The
yield was determined by GC, calibrated using naphthalene
c)
d)
as internal standard. Isolated yield. 20 mol% IMesHCl.
e)
2
0 mol% IMesHCl, 36 h.
With the optimized reaction conditions in hand, a
variety of aryl fluorides 1 were subjected to this C–
F/C–H coupling reaction (Table 2). Biaryl fluorides
worked well under the standard conditions affording
the desired product in moderate to good yields (3a,
3
b). In a similar manner, 1-fluoronaphthalene also
gave the desired product (3c) in good yield.
Remarkably, the reactivity of regular
a)
Reaction conditions: 1a (0.4 mmol), 2a (0.2 mmol),
t
monofluoroarenes was comparable to π-extended
systems. Fluorobenzene afforded the product in a
satisfying yield (3f). Aryl fluorides substituted with a
Ni(cod) (0.04 mmol), IMes•HCl (0.08 mmol), NaO Bu
(0.6 mmol), hexane (1.0 mL), 160 C, 16 h. Isolated
yield. 1r (0.3 mmol) was used.
2
c
o
b)
c)
2
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Advanced Synthesis & Catalysis
10.1002/adsc.201701506
reduced pressure and filled with nitrogen after cooling to
room temperature. After adding aryl fluorides 1 (0.2
mmol), the tube was introduced inside a nitrogen-
To demonstrate the synthetic utility of the present
1
1i
C–F/C–H coupling, a rapid synthesis of texaline
(
important natural product with antitubercular
2
atmosphere glovebox. In the glovebox, Ni(cod) (11.2 mg,
activity) was examined. The coupling reaction of 5-
1,3-benzodioxol-5-yl)-1,3-oxazole with 3-
0.04 mmol), IMes·HCl (27.2 mg 0.08 mmol) and sodium
tert-butoxide (57.7 mg, 0.6 mmol) were added to the tube,
which was sealed with O-ring tap and then taken out of the
glovebox. Then, azoles (0.4 mmol) and cyclohexane (1
mL) were added to the vessel under a nitrogen atmosphere.
The vessel was heated at 160 °C for 16 h in a heating
module with stirring. After cooling the reaction mixture to
room temperature, the mixture was concentrated and
directly purified by preparative thin-layer chromatography
(
4
fluoropyridine 5 underwent smoothly furnishing
texaline 6 in 64% yield using toluene as solvent
(
Scheme 2).
(
PTLC; petroleum ether /ethyl acetate as the eluent) to
afford the product 3.
Acknowledgements
Scheme 2. Synthesis of texaline.
We thank the National Natural Science Foundation of China
(
21602096, 21772020) and Nanchang University (startup fund).
We are also grateful to the Fundamental Research Funds for the
Central Universities (Chongqing University) (No.
106112017CDJXY220007).
On the basis of previous reports,[13] we proposed a
mechanism for this C–F/C–H coupling reaction
(
Scheme 3). Aryl fluoride first coordinates to the
Ni(0) species I and the subsequent oxidative addition References
of aryl fluoride to the Ni(0) center affords the Ni(II)
intermediate II. In the presence of a base,
benzoxazole anion is generated by the deprotonation
of benzoxazole, which could transmetallate with
intermediate II to form the diaryl intermediate III.
Finally, the reductive elimination step furnishes the
product and regenerates the active Ni(0) species.
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COMMUNICATION
Ni-Catalyzed C–F Bond Functionalization of
Unactivated Aryl Fluorides and Corresponding
Coupling with Oxazoles
Adv. Synth. Catal. Year, Volume, Page – Page
+
a
+b
a
Youzhi Yin, Xiaoyu Yue, Qi Zhong, Hanmin
a
b,
b,
Jiang, Ruopeng Bai, * Yu Lan, * and Hua
a,
Zhang *
5
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