Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic Halides at Room Temperature

Article abstract of DOI:10.1002/adsc.201700213

The first photoinduced copper(I)-catalyzed cyanation of aromatic halides at room temperature has been developed. The sp² cyanation reaction exhibits outstanding tolerance to functional groups including primary amines and carboxylic acids, and chemoselectivity to S_N2-reactive alkyl chlorides. Mechanistic investigations indicate that the reaction occurs via a single-electron transfer (SET) between the aryl halide and an excited copper(I) cyanide catalytic intermediate. (Figure presented.).

Full text of DOI:10.1002/adsc.201700213

Title: Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic
Halides at Room Temperature
Authors: Kicheol Kim and Soon Hyeok Hong
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201700213
Link to VoR: http://dx.doi.org/10.1002/adsc.201700213

10.1002/adsc.201700213
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Photoinduced Copper(I)-Catalyzed Cyanation of Aromatic
Halides at Room Temperature
Kicheol Kima and Soon Hyeok Honga,*
a
Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 08826, Republic of Korea
Fax: (+82)-2-889-1568; Phone: (+82)-2-880-6655; e-mail: soonhong@snu.ac.kr
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))
system, developed by the Buchwald group, has
Abstract. The first photoinduced Cu(I)-catalyzed cyanation
of aromatic halides at room temperature has been shown the widest scope of aryl bromides with high
developed. The sp2 cyanation reaction exhibits outstanding
activity among the reported Cu-based catalysts for
sp2-cyanation.[10] Inspired by recent developments by
tolerance to functional groups including primary amines
Fu and Peters,[11],[12]
we envisioned that
and carboxylic acids, and chemoselectivity to SN2-reactive
alkyl chlorides. Mechanistic investigations indicate that the
reaction occurs via single-electron transfer (SET) between
the aryl halide and an excited Cu(I) cyanide catalytic
intermediate.
photoinduced Cu-catalyzed SET may expand the
scope of the reaction, especially with polar and
coordinating substrates that could interfere with two-
electron-based inner-sphere-type catalytic systems.
Herein, we report the first photoinduced Cu(I)-
catalyzed cyanation of aryl halides with readily
available NaCN at ambient temperature. Notably, this
protocol is compatible with diverse aryl halides, polar
reactive functional groups including free amino and
carboxylic acid groups, and even SN2-reactive alkyl
chlorides.
Keywords: Copper; Photocatalysis; Cross-coupling;
Cyanides; Radical reactions
Aromatic nitriles have gained significant attention as
versatile synthetic intermediates and functional
motifs in dyes, pharmaceuticals, and agrochemicals
(Scheme 1A).[1] Because of their importance, various
synthetic protocols have been developed following
“addition of one carbon onto the target aromatic ring”
concept (Scheme 1B).[2] Among the traditional
methods, the Rosenmund–von Braun reaction is
efficient, but suffers from the use of excess CuCN,
tedious purification of Cu wastes, and high reaction
temperature (150–280 °C).[3] Another common
method, the Sandmeyer reaction involving the
diazotization of anilines suffers from explosion
hazard. In industry, ammoxidation with toluene
derivatives under high-pressure O2 and toxic NH3 at
highly elevated temperatures (300–550 °C) is
commonly used but restricted in narrow scope due to
such harsh conditions.[4]
In aromatic nitrile synthesis, catalytic cyanation of
aryl (pseudo)halides has been achieved using mainly
Pd,[1a,1b,5] Ni,[6] and Cu[7] complexes based on the
conventional reactivity of aryl electrophiles with
nucleophilic cyanides at elevated temperatures. Other
catalytic methods via oxidative nitrogenation or C–H
cyanation have also been developed.[8] With the
advantages of low cost and chemical diversity,[9] Cu-
catalyzed C(sp2)-cyanation methods have been
actively developed in the last decade based on a two-
electron pathway utilizing Cun+/Cu(n+2)+ catalytic
cycles.[6] CuI and diamine ligand-based catalytic
Scheme 1. Aromatic nitriles: utility and syntheses.
1
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10.1002/adsc.201700213
Advanced Synthesis & Catalysis
[a]
Recently, the Lectka group reported that bisimine
Conditions: 1a (0.1 mmol), NaCN (1.4 equiv.), 4 (10
ligands were especially effective in Cu(I)-catalyzed
sp3 C–H fluorination via SET.[13] We envisioned that
such bisimine ligands would improve catalytic
activity by preventing the formation of inactive metal
percyanides[14] and by varying the solubility and
electronic properties of the catalysts.[14a] Inspired by
the photoinduced Cu-catalyzed C(sp3)-cyanation of
secondary alkyl chlorides,[11,15] the reaction of 4-
iodobenzonitrile 1a with tetra-n-butylammonium
mol%), MeCN (0.4 mL), Ar, irradiation using four 15W
UV germicidal CFL lamps, r.t. 20 h. Average of 3 runs;
determined by NMR using 1,3,5-trimethoxybenzene as the
internal standard.
cyanide
(TBACN)
was
conducted
using
[CuI(bisimine-CN)] 4 as the photocatalyst under UV-
C irradiation (λmax = 254 nm). The desired product 2a
was obtained in a moderate yield at room temperature
(entry 1, Table 1). To our delight, readily available
NaCN was identified as the best cyanide source
among the tested cyanide sources including
K4[Fe(CN)6] (entry 2, see Table S2 for further
details). Simple Cu(I) salts gave lower yields,
especially in the reactions with other aryl iodides
(entries 3–5).[16] Visible-light irradiation was not
effective (entry 6). The exclusion of Cu, light, or
cyanide did not produce any product (entries 7–9).
Recently, MeCN was reported as a nucleophilic
cyanide source when Cu catalysts and oxidants such
as O2 and TEMPO were used.[17] However, the
reaction did not produce the cyanated product without
NaCN (entry 9). To our delight, the reaction was
comparably efficient even in presence of air and
moisture, demonstrating excellent tolerance of the
developed conditions (entries 10 and 11). Reductive
dehalogenated product 3a was observed as the
byproduct probably by the abstraction of one
hydrogen from the solvent from the generated aryl
radical. Thus, deuterated solvent with stronger C–D
bonds than C–H bonds was used to prevent the side
reaction, but diminished yield was obtained (entry
12).
Scheme 2. Scope of aryl halides. [a] [a] Conditions: 1 (0.3
mmol), NaCN (1.4 equiv.), 4 (10 mol%), MeCN (1.2 mL),
Ar, irradiation using four 15W UV germicidal CFL lamps,
[b]
r.t. 24 h. Isolated yields. NMR yield due to low boiling
point of the product. [c] 36 h. [d] 2 equiv. NaCN and 30 mol%
NaI were used.
With the optimized reaction conditions, diverse
aromatic iodides and bromides were explored
(Scheme 2). Both electron-rich and -deficient
aromatic iodides reacted, affording the products in
Table 1. Optimization of reaction conditions.[a]
moderate-to-excellent
yields
regardless
of
substitution position. Electron-withdrawing cyano (1a
and 1b), acetyl (1c), trifluoromethyl (1e), fluoro (1f
and 1g), and ester groups (1h and 1i) as well as
electronically neutral iodobenzene (1j) were tolerated.
In the case of electron-donating substituents, ether
(1k–n), thioether (1o), alkyl (1p and 1q), and
alcoholic (1r) groups were compatible. In addition,
the developed methods also afforded cyanation with
aryl bromides (1u and 1v) in the presence of 30
mol % NaI.
Entry Deviation from above Conv [%] 2a
3a
[%] [%]
1
2.0 equiv. TBACN
instead of NaCN
none
[CuI] instead of 4
[CuBr] instead of 4
[CuCl] instead of 4
hν (visible light, 34W
blue LED)
100
59
41
2
3
4
5
6
100
100
100
100
0
88
84
86
74
0
12
16
14
26
0
7
no [Cu]
0
0
0
8
no hν
0
0
0
9
no NaCN
under air
1.0 equiv. H2O
CD3CN instead of
MeCN
59
100
100
100
0
0
10
11
12
87
86
82
13
14
0
2
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10.1002/adsc.201700213
Advanced Synthesis & Catalysis
note that reactions with amino acids such as 1al under
the previously reported Cu+/Cu3+-based catalytic
conditions did not afford the corresponding nitrile at
all.
Scheme 3. Cu catalyzed cyanation: our method and the
method in reference 10.
Scheme 5. Chemoselectivity to C(sp2)-cyanation over SN2.
To illustrate the chemoselectivity of the method,[18]
two reactions with SN2-reactive alkyl chlorides,
substituted aryl iodides (1w and 1x) were carried out
[Eqs. (1) and (2), Scheme 5]. To our delight, this
Cu(I) bisimine catalytic system selectively afforded
C(sp2)-cyanated products 2w and 2x without C(sp3)-
cyanation on alkyl chlorides, which is difficult to
achieve with the previously reported catalytic
systems operated at high temperatures. The reaction
of 1x under the reported photoinduced C(sp3)-
cyanation conditions[11] furnished only the C(sp3)-
cyanated and reductively dehalogenated product 5x in
a quantitative yield [Eq. (3), Scheme 5]. These results
clearly indicate that this method can be used to
selectively functionalize aryl rings differently with
the traditional SN2 and recently reported
photocatalytic C(sp3)-cyanation protocols.
Scheme 4. Scope of aryl iodides with polar functional
groups. [a] [a] Conditions are same with Scheme 2. Isolated
[b]
yields.
After the cyanation, the carboxylic acid was
[c]
esterified
After the cyanation, the amine was Boc-
protected, and then the carboxylic acid was esterified.
A carboxylic acid, 3-iodophenylacetic acid (1aj),
which was not compatible in the previously reported
Cu+/Cu3+-based catalytic system,[10] was cyanated
although the isolated yield (30%) after esterification
was not so high (Scheme 3). Encouraged by the result,
we applied the developed method to highly polar
functional groups which were usually less compatible
in transition-metal catalysis. The developed method
tolerated amino groups, free carboxylic acid, amino
acids, and medicinally relevant heterocycles[1c]
(Scheme 4). Pyridine derivatives including quinolone
(1aa–1ad) successfully afforded the coupling
products in good-to-quantitative yields despite their
high affinity toward a transition metal center. Even
free indole (1ae) and free anilines (1af–1ai) were
smoothly transformed to the desired products in
moderate yields. However, the reactions with
thiophene derivatives such as 2-iodothiophene did not
give any desired product, affording dehalogenated
thiophene only. Notably, amino acid derivatives
including unprotected amino acid (1ak–1am)
tolerated the catalytic conditions. It is worthwhile to
Figure 1. Investigation of photocatalysis. A) light-dark
experiment. B) reaction profile during catalysis.
3
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10.1002/adsc.201700213
Advanced Synthesis & Catalysis
Photoirradiation is essential in the developed
and Cu(I) halide. To gain a deeper mechanistic
insight, a kinetic study was performed (Scheme 8).
All the reaction species (aryl iodide 1a, Cu 4, and
cyanide) showed first-order dependence on the
concentration. These results indicate that the reaction
of copper cyanide adduct with aryl species is the
turnover limiting step, which could be the SET or the
cross-coupling step in the proposed mechanism.
Besides, Cu(I) halide seems to be a catalyst resting
state in equilibrium via reversible cyanide exchange,
regarding the first order of cyanide. Interestingly,
relatively large equivalence of cyanide (up to 1.8
equiv.) compared to copper catalyst did not hamper
the reactions. Chelation of the bidentate bisimine
ligand presumably inhibits the formation of
percyanide complex. Much higher concentrations of
Cu and cyanide hindered the reactions. In high
concentrations of Cu, comproportionation of Cu(I)
might occur, giving catalytically inactive Cu(0) and
Cu(II) species.[19] In the presence of excess cyanides,
Cu percyanide species could be formed as dead-end
species similar to Pd catalysis.[14a]
method as no conversion occurred without light
(entry 8, Table 1). Light–dark experiment with 1a
further confirmed that the reaction proceeded only
with irradiation (Figure 1A). The involvement of
radical intermediates in photocatalysis was also
investigated using four radical scavengers such as
TEMPO (Scheme 6). All the reactions with 1a were
arrested in moderate-to-high degree (36–67%
decrease in yield). Regarding the gradual conversion
of aryl iodide (Figure 1B) and incomplete inhibition
by radical scavengers, a catalytic amount of aryl
radical may be present within the solvent cage
following closed catalytic cycle rather than a rapid
chain process.
In conclusion, we developed a novel mild
cyanation method for aryl halides at room
temperature using a Cu(I) photocatalytic system. This
method tolerates various functional groups including
reactive free amino and carboxylic groups, which
were previously incompatible in two-electron-based
Cun+/Cu(n+2)+ sp2 cyanation reactions. The method
also exhibited excellent chemoselectivity in the
cyanation of aryl halides even in presence of SN2-
reactive alkyl chlorides.
Scheme 6. Inhibition with radical scavenger.
Experimental Section
To an oven-dried quartz tube (10 cm in height, fitted with a
14/20 septum) equipped with a stir bar, (if solid) 1 (1
equiv., 0.3 mmol), 4 (10 mol%), and NaCN (1.4 equiv.)
were added in an Ar-filled glovebox. The quartz tube was
capped with a 14/20 septum after CH3CN (1.2 mL) was
added via a syringe. After removing from the glovebox, the
reaction tube was sealed again with a black-vinyl-electrical
tape (if 1 is liquid, it was added via a microsyringe at this
time). The resulting mixture was stirred vigorously and
irradiated in the center of the lamps at room temperature
for 24 h. Then, the reaction mixture was transferred to a
round-bottom flask using acetone or CH2Cl2 and then
concentrated under reduced pressure. The residue was
purified by column chromatography using a mixture of
hexane/ethyl acetate or CH2Cl2/methanol eluents used.
Scheme 7. Plausible mechanism.
1.6
1.3
1
2.5
2
1.6
1.4
1.2
1
1.5
1
y = 0.0166x + 0.3793
y
=
0.0099x
- 2.2393
0.7
0.4
y
=
0.0023x
+ 0.0636
0.5
0
0.8
0.6
R² = 0.9904
R² = 0.9895
Acknowledgements
R² = 0.9475
10
35
[Cu] (mM)
60
85
300
400
500
600
200
300
[Ar-I] (mM)
400
500
[CN-] (mM)
We thank Jaewoon Kim in our group for helpful discussion. This
work was supported by Samsung Science and Technology Foun-
dation under Project Number SSTF-BA1601-12.
Scheme 8. Kinetic study.
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Based on the experiments and the previous
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(Scheme 7).[12h] Cu(I) cyanide is formed from Cu(I)
halide via anion exchange. The adduct is first
photoexcited and then quenched with the aryl halide
via SET, furnishing Cu(II) cyanide and an aryl radical.
Next, they combine to generate an aromatic nitrile
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5
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Advanced Synthesis & Catalysis
COMMUNICATION
Photoinduced Copper(I)-Catalyzed Cyanation of
Aromatic Halides at Room Temperature
Adv. Synth. Catal. Year, Volume, Page – Page
Kicheol Kim and Soon Hyeok Hong,*
6
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