Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation

Article abstract of DOI:10.1021/acs.orglett.6b02553

Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)₃ as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.

Full text of DOI:10.1021/acs.orglett.6b02553

Letter
pubs.acs.org/OrgLett
Visible-Light Photoredox Borylation of Aryl Halides and Subsequent
Aerobic Oxidative Hydroxylation
Min Jiang, Haijun Yang, and Hua Fu*
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry,
Tsinghua University, Beijing 100084, China
*
S Supporting Information
ABSTRACT: Efficient and practical visible-light photoredox borylation
of aryl halides and subsequent aerobic oxidative hydroxylation were
developed. The protocols use readily available aryl halides and
bis(pinacolato)diboron as the starting materials, fac-Ir(ppy) as the
3
photocatalyst, and corresponding arylboronic esters and phenols were
obtained in good yields. The methods show some advantages including
simple equipment, mild conditions, easy operation, and wide substrate
scope. Therefore, they should provide a valuable strategy for chemical transformations.
rylboronic acids and esters are important building blocks for
borylation of aryl halides and subsequent aerobic oxidative
hydroxylation.
A
the formation of aryl carbon−carbon or carbon−
1
heteroatom bonds. Traditional synthetic methods use couplings
of arylmetallic intermediates with trialkyl borates, followed by
transesterification or hydrolysis. Some drawbacks include limited
First, visible-light photoredox borylation of 1-iodo-4-methox-
ybenzene (1e) with 1.5 equiv of bis(pinacolato)diboron (2) was
selected as the model to optimize conditions including
photocatalysts, additives, solvents, time, and amount of reactants.
As shown in Table 1, three transition-metal photocatalysts, fac-
Ir(ppy) (A), [Ir(ppy) ](dtbbpy)PF (B), and[Ru(bpy) ]Cl
2
functional group tolerance and anhydrous conditions. Recently,
transition-metal-catalyzed borylation of aryl halides was a
popular strategy, and some efficient methods were built to
3
2
6
3
2
3
n
convert aryl C−X bonds to C−B bonds. Several transition-
(
C), were screened using 2.0 equiv of Bu N as the additive
3
4
metal-free borylations of aryl halides were also established.
and MeCN as the solvent under Ar atmosphere and irradiation of
visible light with 23 W compact fluorescent light (CFL) for 24 h
5
More interestingly, direct C−H borylation in the presence or
6
absence of transition metals was presented. In addition,
(
1
entries 1−3), and fac-Ir(ppy) provided the highest yield (entry
3
7
aromatic nitrogen-containing compounds such as amines,
n
). No reaction was observed in the absence of Bu N (entry 4).
3
8
9
diazonium salts, and aryl triazenes are also used as starting
materials to prepare arylboronic acid derivatives. Although these
methods are useful, the limited substrates, harsh conditions,
special additives, and/or longer times are usually observed.
n
Yields increased when the amount of Bu N was increased
3
(
entries 5 and 6). Reaction in a mixed solvent of MeCN and
water led to higher yields (entries 7 and 8). When 2.0 equiv of 2
was used, an 89% yield was afforded (entry 9). Methanol was not
a suitable solvent (entry 10). Yield decreased when the time was
1
0
Recently, photoinduced chemical transformations with UV
1
1
and visible light have emerged as a powerful activation
protocol, and some interesting reactions have been developed
shortened (compare entries 9, 11, and 12). We attempted Et N
3
and diisopropylethylamine (DIPEA) as additives, and they
provided lower yields (entries 13 and 14). No reaction occurred
in the absence of light (entry 15).
1
2,13
via photoinduced aryl carbon−halogen bond dissociation.
Very recently, several groups reported metal-free UV photo-
1
4
induced borylation of haloarenes, in which specialized
equipment was required. Distinctly, it is more convenient and
practical to use domestic light sources and standard laboratory
glassware in visible-light photocatalysis, and the electron transfer
between the catalysts and substrates upon photoexcitation makes
a reaction milder than the analogous energy-transfer character-
With optimized visible-light photoredox conditions, the
substrate scope for borylation of 1 with 2 was surveyed. As
shown in Table 2, aryl iodides displayed reactivity higher than
that of aryl bromides. Note that electron effects on the aryl
iodides did not show obvious difference in reactivity, but aryl
bromides containing electron-withdrawing groups exhibited
higher reactivity than those containing electron-donating groups.
Halonaphthalenes and 4-halobiphenyl were good substrates
(3q−s). Reaction of 1,4-dibromobenzene with 4.0 equiv of 2
provided bisborylating product 3t in 70% yield. The visible-light
photoredox borylation displayed tolerance of various functional
15
istics of UV photochemistry. Recently, eosin-Y-catalyzed
borylation of aryldiazonium salts under irradiation of visible
16
light was developed. Furthermore, synthesis of phenols from
17
arylboronic acids has been well-developed. Recently, two
groups independently described visible-light-induced aerobic
oxidative hydroxylation of arylboronic acids under [Ru-
1
8a
18b
(
bpy) Cl ]·6H O
or methylene blue catalysis.
As our
3
2
2
19
continuing study on visible-light photoredox catalysis, we
Received: August 25, 2016
report an efficient and practical visible-light photoredox
©
XXXX American Chemical Society
A
DOI: 10.1021/acs.orglett.6b02553
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
Table 1. Optimization of Conditions for Visible-Light
Photoredox Borylation of 1e with 2
Table 2. Substrate Scope for Visible-Light Photoredox
a
a
Borylation of 1 with 2
additive
(equiv)
time
(h)
yield
b
entry PC
solvent
MeCN
(%)
c
n
n
n
n
n
n
n
n
n
n
n
n
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
A
B
C
Bu N (2)
3
24
24
24
24
24
24
24
24
24
24
12
36
24
24
24
25
6
c
c
c
c
c
c
c
d
Bu N (2)
3
MeCN
MeCN
MeCN
MeCN
MeCN
Bu N (2)
3
trace
NR
32
44
72
80
89
62
76
89
58
60
NR
Bu N (2)
3
A
A
A
A
A
A
A
A
A
A
A
Bu N (4)
3
Bu N (5)
3
Bu N (5)
3
MeCN/H O (9:1)
2
Bu N (5)
3
MeCN/H O (19:1)
2
Bu N (5)
3
MeCN/H O (19:1)
2
d
d
d
d
d
d
0
1
2
3
4
5
Bu N (5)
3
CH OH
3
Bu N (5)
3
MeCN/H O (19:1)
2
Bu N (5)
3
MeCN/H O (19:1)
2
NEt (5)
MeCN/H O (19:1)
3
2
a
DIPEA (5)
MeCN/H O (19:1)
2
Reaction conditions: Ar atmosphere and visible-light irradiation 23 W
,
e
n
n
Bu N (5)
3
MeCN/H O (19:1)
CFL, 1 (0.2 mmol), 2 (0.4 mmol), fac-Ir(ppy) (2.0 μmol), Bu N
2
3
3
a
(1.0 mmol), MeCN (1.9 mL), H O (0.1 mL), rt (∼25 °C), 24 or 36 h
Reaction conditions: Ar atmosphere and visible-light irradiation, 1e
0.2 mmol), photocatalyst (PC) (2.0 μmol), additive (0.4−1.0 mmol),
solvent (2.0 mL), rt (∼25 °C), 12−36 h in a sealed Schlenk tube.
2
b c
in a sealed Schlenk tube. Isolated yields. 0.8 mmol of 2.
(
b
c
d
e
Scheme 1. Control Experiment in the Presence of PhSeSePh
for Mechanism Investigation
Isolated yield. 0.3 mmol of 2. 0.4 mmol of 2. No light. NR = No
reaction.
groups including ethers (3e,f), C−Cl bond (3g−i), ketone (3j),
aldehyde (3k), nitriles (3l,m), esters (3n,o), and CF (3p).
3
To disclose the mechanism for the borylation of aryl halides,
reaction of 1e with 2 in the presence of diphenyl diselenide was
performed under the standard conditions, and 3b and I were
obtained in 39 and 37% yields, respectively (Scheme 1). The
experiment showed that the aryl radical was generated during the
reaction. Furthermore, electron spin resonance (ESR) spectra of
various mixtures were recorded under visible-light irradiation (λ
>
420 nm) using 5,5-dimethyl-1-pyrroline N-oxide (DMPO) as
the radical trapping agent (Figure 1). (a) When treatment of
iodobenzene (1a) (50 mM), fac-Ir(ppy) (1 mol %), tributyl-
3
amine (TBA) (50 mM), 2 (50 mM), and DMPO (100 mM) was
performed, two groups of radical signals were observed as
follows: a sextet peak signal (marking with the stars) with a g
value of 2.003, AN = 1.46 mT, AH = 2.15 mT corresponding to a
carbon-centered radical, and the other quartet peak signal
(
marked with triangles) with a g value of 2.002, AN = 1.35 mT,
AH = 1.49 mT corresponding to a nitrogen-centered radical
Figure 1a). (b) Only weak radical signals were observed in the
Figure 1. ESR spectra of various mixtures under irradiation of visible
light for 6 min: (a) mixture of 1a (50 mM), fac-Ir(ppy) (1 mol %), TBA
3
(
(50 mM), 2 (50 mM), and DMPO (100 mM) in CH CN; (b) mixture
3
absence of 2 (Figure 1b), which displayed that 2 could promote
formation of radicals. (c) No radical signal was observed in the
absence of 1a (Figure 1c), and the experiment showed that aryl
halide was an electron acceptor. (d) A result similar to that in
Figure 1c was found without addition of TBA (Figure 1d), which
indicated that TBA was a radical initiator.
of 1a (50 mM), [fac-Ir(ppy)
] (1 mol %), TBA (50 mM), and DMPO
3
(
100 mM) in CH CN; (c) mixture of TBA (50 mM), fac-Ir(ppy) (1
3
3
mol %), 2 (50 mM), and DMPO (100 mM) in CH CN; (d) mixture of
3
1
a (50 mM), fac-Ir(ppy) (1 mol %), 2 (50 mM), and DMPO (100
3
mM) in CH CN.
3
A possible mechanism for the visible-light photoredox
borylation of aryl halides is proposed in Scheme 2 according to
the results above. Treatment of 2 with water in the presence of
14b
TBA (n-Bu N) leads to A and B. Irradiation of photocatalyst
3
B
DOI: 10.1021/acs.orglett.6b02553
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
Scheme 2. Proposed Mechanism for Visible-Light Photoredox
Borylation of Aryl Halides (4) with 2
Table 3. Substrate Scope for One-Pot, Two-Step, Visible-
a
Light Photoredox Synthesis of Phenols from 1
Ir(III) with visible light gives the excited-state *Ir(III), and a
single-electron transfer of n-Bu N to *Ir(III) provides Ir(II)
3
leaving C. Reaction of Ir(II) with aryl halide (1) donates radical
anion D, regenerating photocatalyst Ir(III). Desorption of
−
halogen anion (X ) from D gives aryl radical E, and treatment
of E with A affords radical anion G. Finally, one single-electron
transfer of G to *Ir(III) provides the target product (3) and
Ir(II).
Inspired by the excellent results above, we extended the
substrate scope to alkyl bromides. As shown in Scheme 3,
a
Reaction conditions: Ar atmosphere and visible-light irradiation with
Scheme 3. Visible-Light Photoredox Borylation of 4 with 2
2
3 W CFL, 1 (0.2 mmol), 2 (0.4 mmol), fac-Ir(ppy) (2.0 μmol),
3
n
N Bu (1.0 mmol), MeCN (1.9 mL), H O (0.1 mL), rt (∼25 °C),
same borylation time as in Table 2 in a sealed Schlenk tube; 16 h in an
opened Schlenk tube. Isolated yields. 0.8 mmol of 2.
3
2
b
c
In summary, we have developed an efficient and practical
visible-light photoredox borylation of aryl halides with bis-
reaction of alkyl bromides with 2 under the standard conditions
provides alkylboronic esters in moderate yields. We also
attempted reaction of aryl iodides with bisboronic acid (6),
and the corresponding arylboronic acids were obtained (Scheme
(
pinacolato)diboron under catalysis of fac-Ir(ppy) , and the
3
subsequent aerobic oxidative hydroxylation of the obtained
arylboronic esters in air provided various phenols. Reactions
were performed at room temperature and exhibited good
functional group tolerance. Therefore, the present methods show
some advantages for the synthesis of arylboronic esters and
phenols. We believe that the novel discovery will find wide
applications in some fields.
4
). Unfortunately, the reaction was inferior to the borylation of
aryl halides using 2 as the borylating agent.
Scheme 4. Visible-Light Photoredox Borylation of 1 with 6
ASSOCIATED CONTENT
■
*
S
Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.orglett.6b02553.
Experimental details and figures (PDF)
In 2012, photoredox-catalyzed oxidation of boronic acids and
AUTHOR INFORMATION
18a
■
esters was described. As shown in Table 3, we investigated
one-pot, two-step, visible-light photoredox synthesis of phenols
from 1, including borylation of aryl halides and hydroxylation of
arylboronic esters. For borylation of aryl halides, the visible-light
photoredox catalytic conditions were the same as those in Table
Corresponding Author
*E-mail: fuhua@mail.tsinghua.edu.cn.
Notes
The authors declare no competing financial interest.
2
. When the borylation of aryl halides was complete, the sealed
Schlenk tube was opened, and the subsequent aerobic oxidative
hydroxylation of arylboronic esters for 16 h provided the
corresponding phenols with various functional groups. The
mechanism is similar to that in previous literature. Therefore, it
is easy to make phenols using 1 and 2 as the starting materials.
ACKNOWLEDGMENTS
■
The authors thank the National Natural Science Foundation of
China (Grant Nos. 21372139 and 21221062), and Shenzhen Sci
& Tech Bureau (CXB201104210014A) for financial support.
18
C
DOI: 10.1021/acs.orglett.6b02553
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
(
8) (a) Dewhurst, R. D.; Neeve, E. C.; Braunschweig, H.; Marder, T. B.
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DOI: 10.1021/acs.orglett.6b02553
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