Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex

Article abstract of DOI:10.1039/d0ob00028k

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.

Full text of DOI:10.1039/d0ob00028k

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DOI: 10.1039/D0OB00028K
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Visible-light-mediated borylation of aryl and alkyl halides with a
palladium complex
Received 00th January 20xx,
a,†
Jia-Hui Zhao, Zhao-Zhao Zhou,a,b,† Yue Zhang,a Xuan Su,a Xi-Meng Chenb and Yong-Min Liang*a
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Palladium catalyzed visible-light-mediated borylation of
inactivated aryl and alkyl halides was reported, the method had
high yield and excellent functional group compatibility.
Furthermore, arylsilicate were synthesized selectively by
dimethylphenylsilyl boronic ester via changing the reaction
conditions. Finally, the possible reaction mechanism is given
through the fluorescence quenching experiment and turn on/off
experiment.
Organoboron compounds, especially alkyl/aryl boronic acid
derivatives, are highly valuable building blocks used in Suzuki
coupling reaction in modern synthetic chemistry.[1] Classical
methods to alkyl/aryl boronates include transmetallation with
Grignard and lithium reagents,[2] hydro-boration of olefins,[3]
and C-H activation/borylation reactions.[4] However,
drawbacks such as strict conditions, limited substrate scope
and regioselectivity make it urgent to develop a direct
approach to organoboronates. The first example of palladium-
catalyzed borylation reaction of aryl iodides and bromides was
reportedby Miyaura in 1995.[5] Subsequently, borylation of
carboxylic acid,[6] alkylamine[7] and alcohol derivatives[8] has
been widely explored. Considering the atom economy and cost
of substrates, aryl/alkyl halides still are the most widely
employed reagents for the borylation reaction via the
transition-metal catalysis,[9] such as Cu,[11] Ni,[12] Fe,[13] Co,[14]
Zn[15] and Mn,[16] which was coordinated with the ligands such
as NHC,[11d, 15a] dtbpy[12b, 15b] and pybox.[12a, 18c]
Scheme 1. Recent approaches to radical borylation.
palladium-catalyzed
dehalogenation
hydrogenation
/deuteration of inactivated aryl/alkyl bromides and chlorides,
and it indicated that the palladium complex could be an ideal
photocatalyst to activate alkyl bromides or even chlorides.[19]
In this paper, we reported the first visible-light-mediated
palladium-catalysed dehalogenative borylation reaction.
The initial system was chosen for the borylation of 3-
phenoxypropyl bromide (3a) by employing Pd(OAc)2 (3 mol %) and
PPh3 (6 mol %) at room temperature with DMF under blue LEDs.
The borylation product 3aa was detected by GC-MS in 43% yield
with full conversion of 3a after 8h (entry 1, Table 1). Screening of
solvents reveals MeCN to be the optimal solvent (entries 1-5, Table
1). Ligands such as Xantphos, DPEphos etc. showed negative effect
on the results (entries 6-9, Table 1). Investigation of the base
showed a decreased ratio of 3aa when other base (tBuOK, KOMe
etc.) was used, probably because the strong base would lead to the
decomposition of 3aa (entries 10-14, Table 1). Further optimization
of palladium catalysts indicated that Pd(PPh3)4 owned the best
catalytic efficiency with 55% isolated yield (entries 15-17, Table 1).
In recent decades, novel strategies in radical chemistry,
especially photo chemistry, provide an alternative method
during the construction of C-B bond.[17] However, the alkyl/aryl
iodides, because of its lower bond energy and redox potential
compared with the bromides, are widely employed.[18]
Recently, our group developed the visible-light-mediated
a. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou
730000, P.R. China. E-mail: liangym@lzu.edu.cn.
b. School of Nuclear Science and Technology, Lanzhou University, Lanzhou 730000,
P.R. China.
† These two authors contributed equally to this article.
Electronic supplementary information (ESI) available. CCDC2000793. For ESI and
crystallographic data in CIF or other electronic format see DOI:
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Table 2. Scope of dehalogenative borylation substrates.a
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Table 1. Optimization of the Reaction Conditions.a
DOI: 10.1039/D0OB00028K
entries
1
catalyst
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(PPh3)4
Pd2(dba)3
Pd(PPh3)2Cl2
-
ligand
PPh3
PPh3
PPh3
PPh3
PPh3
Xantphos
DPEphos
dipy
BINAP
PPh3
PPh3
PPh3
PPh3
PPh3
-
solvent
DMF
base
K3PO4
K3PO4
Yielda
43%
30%
36%
41%
54%
none
33%
none
Trace
28%
42%
Trace
33%
24%
2
THF
3
dioxane K3PO4
PhMe K3PO4
4
5
MeCN K3PO4
MeCN K3PO4
MeCN K3PO4
MeCN K3PO4
MeCN K3PO4
MeCN Cs2CO3
MeCN K2CO3
MeCN tBuOK
6
7
8
9
10
11
12
13
14
15
16
17
18
19
MeCN
KOMe
MeCN
DBU
MeCN K3PO4 75%(55%b)
-
MeCN K3PO4
MeCN K3PO4
MeCN K3PO4
None
15%
-
-
None
None
None
a Reaction conditions: 1aa-3ca, 4aa, 4ba (0.2 mmol), Pd(PPh3)4 (3 mol %), K3PO4
(2.0 equiv), B2pin2 (2.0 equiv), MeCN (2 mL), blue LEDs, Ar, 25oC, 8h. The
conversions and yields were determined by GC-MS using n-dodecane as an
Pd(PPh3)4
-
MeCN
-
20c
Pd(PPh3)4
-
MeCN K3PO4
b
c
internal standard. Isolated yield. 3da-3ha (0.2 mmol), B2cat2 (2.0 equiv),
Pd(PPh3)4 (3 mol %), KOMe (2.0 equiv), MeCN (2 mL), blue LEDs, Ar, 25oC; pinacol
(0.8 mmol), NEt3 (0.7 mL), 1 h; d 1kb (0.2 mmol), Pd(PPh3)4 (3 mol %), K3PO4 (2.0
a Reaction conditions: 3a (0.2 mmol), catalyst (3 mol %), ligand (6 mol %), base
(2.0 equiv), B2pin2 (2.0 equiv), solvent (2 mL), blue LEDs, Ar, 25oC, 8h. The
conversions and yields were determined by GC-MS using n-dodecane as an equiv), B2pin2 (3.0 equiv), MeCN (2 mL), blue LEDs, Ar, 25oC, 10h.
internal standard. b Isolated yield. c In dark.
(1na). Heterocyclo- and naphthyl-bromides were borylated in
Meanwhile, control experiment indicated that both palladium
catalyst and base are essential for this photo-induced
dehalogenative borylation process. Finally, the optimized
conditions were confirmed as: Pd(PPh3)4 (3 mol %), K3PO4 (2.0
equiv) with MeCN under blue LEDs at room temperature under
argon for 8h. Furthermore, 3-bromoanisole (1g) was chosen as
model substrate for the borylation of aryl bromide and the
optimal conditions were Pd(PPh3)4 (3 mol %), K3PO4 (2.0 equiv.)
with MeCN under blue LEDs at room temperature under argon
for 8h (See ESI).
moderate to excellent yields. However, ortho bromides (2ba
,
2da) showed dramatic decline in yields comparing with 2aa
and 2ea. The borylation of alkyl C-Br bond is usually difficult in
thermodynamic Pd-catalyzed cross-coupling because of
protonation and β-H elimination reaction.[20] Fortunately,
inactivated primary alkyl including ether (3aa), alkane (3ba),
ethyl benzene (3ca), and benzyl (4ba) formed desired products
smoothly in good yields. Notably, B2Pin2 and K3PO4 were not
suitable for secondary and tertiary alkyl bromides due to lower
activity. To overcome the problem, another borylation reagent
bis(catecholato)diboron (B2cat2) and stronger base (KOMe)
Then, the optimized conditions were firstly applied to aryl
bromides or chlorides at 0.2 mmol scale as shown in Table 2. For
aryl bromides, high conversions and good to excellent yields were
obtained for some of the substrates, even including the
were applied in borylation of this sort of alkyl bromides (3da
-
3ga). As expected, the desired products were obtained in
moderate to good yields. It has been revealed that the
secondary and tertiary alkyl bromides need to trap a carbon-
radical with B2cat2 very fast to avoid dehalogenation.[21]
Delightly, the allyl and benzyl bromides were suitable for this
reaction and generated the desired products 4aa and 4ba with
excellent yields.
onesholding an electron-withdrawing group (1ha
Meanwhile, moderate to good yields were included in the
substrates with an electron-rich group (1aa 1ga). Aryl
-1ja).
-
chlorides could also be ideal substrates (1ka-1la) and the
reaction of 4-bromochlorobenzene generated two products,
monoborylated (1ka, 42%) and diborylated (1kb, 48%) almost
in equal yields. Furthermore, vinyl bromide could produce
vinyl borates in moderate yield (1ma). A derivative of L-
menthol was also evaluated, and it gave 40% isolated yield
2 | J. Name., 2012, 00, 1-3
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DOI: 10.1039/D0OB00028K
Scheme 3. Selective borylation and siliconization.
Figure 1. Turn on/off experiment of 3-bromoanisole with GC-MS and used
dodecane (0.1 mmol) as standard.
Scheme 4. Derivative reactions.
In order to further explore the potential of this
dehalogenative borylation process, dimethylphenylsilyl
boronic ester (5a) was successfully applied as a silylation and
boronylation reagent respectively in modified conditions. This
reaction had a broad application range, and greatly increases
the spectrum of its application (Scheme 3).[22] Based on the
above results, we further evaluated the utility of the
organoboron compounds. 2-napthaleneboronic acid pinacol
ester (2ea) was converted smoothly to naphthol (6aa),
Scheme 5. Proposed mechanism.
With the obtained details in the hand and our previous work,[19]
the proposed mechanism of palladium catalyzed boronylation
under LED light is speculated. At first, aryl/alkyl halides produce
aryl/alkyl radical intermediates through single electron reduction
progress with excited state palladium catalyst. Then, aryl/alkyl
radical adds to B2Pin2 to form intermediate I, which is subsequently
converted to intermediate II under the activation by base. Because
of the favored energy in homolysis of II, the B-B bond cleaves to
give the desired product 2 and III. Finally, the intermediate III is
oxidized by Pd(I) intermediate through single-electron-transfer (SET)
to form IV, which completes the catalytic cycle.[21] The mechanism
of palladium catalyzed silylation under LED light is also proposed. At
first, aryl halides produced aryl radical intermediates through SET
progress with excited state palladium catalyst. Then, aryl radical
combined with palladium catalyst under 5a and base, produced
intermediate V and intermediate VI. At last, the desired productwas
methylnaphthalene
(6ba), naphthylamine
(6ca), and
naphthalene nitrile (6da) under different reaction conditions in
moderate to excellent yields. These data extend the practical
value of organoboron compounds (Scheme 4).[23]
In order to get more insights of the reaction, a series of
studies were carried out to uncover the mechanism. First of all,
we used TMEPO, a free radical trapping agent as the additive
to the reaction. The reaction was totally inhibited, which
indicated that the reaction might be a free radical mechanism
(See ESI). After that, we carried out the turn on/off experiment
and the reaction was tracked continuously by GC-MS within 14
h. In the initial two hours, more than 70% product was
produced during the first and second light-on periods (0-30
min and 60-90 min). Because a small number of intermediates
still presented after rapid reaction, there were slight increases
in the first and second light-off periods (30-60 min and 90-120
min). During 2 to 10 h, the yield increased by only 27% due to
a decrease in the reaction rate and there was no increase in
yield in off light periods. To our surprise, the yield of reaction
began to decrease after 10 h and eventually dropped to about
70%. Finally, emission spectrum experiment was carried out on
the reaction system, and the λmax of Pd(PPh3)4 was obtained.
We use haloalkanes and haloarenes as fluorescence quenching
reagents to obtain the two Stern-Volmer plots. This may be
the evidence that Pd(PPh3)4 in the excited state first transfers
electrons to halogenated reagents to generate corresponding
free radicals (see ESI).[24]
generated after intermediate
elimination.[25]
V
proceeding the reductive
Conclusions
In summary,
a novel method of visible-light-mediated
palladium catalyzed borylation of aryl and alkyl halides has
been accomplished in this study. At the same time, we also
tried to conduct silylation reaction of aryl bromides to expand
its application range. This reaction represents a good
compatible method to some difficult problems in borylation.
Conflicts of interest
There are no conflicts to declare.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
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Acknowledgements
DOI: 10.1039/D0OB00028K
Dei enberger, A. Eichhorn, P. G. Steel, Z. Lin and T. B.
This work was supported by the National Natural Science
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