Highly active cobalt complex catalysts used for alkene hydrosilylation

Article abstract of DOI:10.1002/aoc.6315

A series of nitrogen phosphine ligands were synthesized, and the hydrosilylation reaction of alkenes catalyzed using MCl₂ in the presence of these ligands was investigated. FeCl₂/1(N¹, N¹, N², N²-Tetrakis[(diphenylphosphino)methyl]ethane-1,2-diamine) showed low catalytic activity. MnCl₂/1, CrCl₃/1 and NiCl₂/1 showed some catalytic activity. The CoCl₂/N,P-ligand catalyst system showed high activity as well as excellent selectivity (The selectivity of the β-adduct was ~100%.) in the hydrosilylation reaction. CoCl₂/1 showed the highest catalytic activity (~ >99.9% conversion of 1-octene). Additionally, no α-adduct, dehydrogenative silylation product and octane were detected.

Full text of DOI:10.1002/aoc.6315

Received: 15 March 2021
DOI: 10.1002/aoc.6315
Revised: 10 May 2021
Accepted: 10 May 2021
S H O R T C O M M U N I C A T I O N
Highly active cobalt complex catalysts used for alkene
hydrosilylation
Yu Liu
| Jiayun Li
| Ying Bai
| Jiajian Peng
Key Laboratory of Organosilicon
Chemistry and Material Technology of
Ministry of Education, Hangzhou Normal
University, Hangzhou, China
A
series of nitrogen phosphine ligands were synthesized, and the
hydrosilylation reaction of alkenes catalyzed using MCl2 in the presence of these
ligands was investigated. FeCl2/1(N1, N1, N2, N2-Tetrakis[(diphenylphosphino)
methyl]ethane-1,2-diamine) showed low catalytic activity. MnCl2/1, CrCl3/1
and NiCl2/1 showed some catalytic activity. The CoCl2/N,P-ligand catalyst sys-
tem showed high activity as well as excellent selectivity (The selectivity of the
β-adduct was ꢀ100%.) in the hydrosilylation reaction. CoCl2/1 showed the
highest catalytic activity (ꢀ >99.9% conversion of 1-octene). Additionally, no
α-adduct, dehydrogenative silylation product and octane were detected.
Correspondence
Jiayun Li and Jiajian Peng, Key
Laboratory of Organosilicon Chemistry
and Material Technology of Ministry of
Education, Hangzhou Normal University,
Hangzhou 311121, China.
Email: jiayun1980@hzun.edu.cn; jjpeng@
hznu.edu.cn
K E Y W O R D S
Funding information
Zhejiang Provincial Technologies R&D
Program of China, Grant/Award Number:
2017C31105; Natural Science Foundation
of Zhejiang Province, Grant/Award
Number: LY18B020012
alkene, CoCl2, hydrosilylation, phosphine ligands
1 | INTRODUCTION
Verhoeven et al.[17] reported the catalytic activity of
well-characterized Co (II) and Co(I) complexes bearing
The hydrosilylation of alkenes has emerged as a
powerful method in organic synthesis.[1–3] The catalytic
hydrosilylation of alkenes is a valuable transformation
because it generates silicon-containing compounds,
such as silane coupling agents. Platinum catalysts, such
as Speier et al.'s[4] and Karstedt and Scotia's[5] cata-
lysts, which exhibit high catalytic activity, have been
widely used in various hydrosilylation reactions. How-
ever, platinum catalysts have some drawbacks, such as
their high price, low compatibility towards substrates,
and the occurrence of side reactions. In addition, many
transition metal complexes, such as rhodium, iridium,
iron, and cobalt, are known to be catalysts for
hydrosilylation of alkenes.[6–9] However, they still
possess many drawbacks, such as low catalytic activity
and reaction selectivity. Therefore, there has been an
increasing demand for cheap metal catalysts with
high catalytic activity and reaction selectivity.[10–16]
p-Toldpbp ligands observed in the hydrosilylation of
1-octene using phenylsilane. The cobalt complexes
featuring N-heterocyclic carbene, β-diketiminato, and
2, 6-diiminopyridine ligands are found effective in
catalyzing alkene hydrosilylation reactions. In addition,
there are some studies on hydrosilylation reactions
catalyzed by cobalt salts.[18–30]
Our group has paid a great deal of attention to
cobalt complexes, which are recognized as earth-
abundant metal catalysts, which can be used to replace
precious metals, for use as catalysts in the
hydrosilylation of alkenes. The utility of cobalt
complexes as hydrosilylation catalysts has been known
for a long time, although most of the examples suffer
from low reaction selectivity. In this paper, we report
that several cobalt P-ligand complex catalysts act as
effective alkene hydrosilylation catalysts under mild
reaction conditions.
Appl Organomet Chem. 2021;e6315.
wileyonlinelibrary.com/journal/aoc
© 2021 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.6315

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LIU ET AL.
2 | EXPERIMENT
2.1 | General methods
reaction, the conversion of the alkene and selectivity
were determined using GC.
Styrene was washed with 5% NaOH and dried with
Na2SO4 and then was distilled under reduced pressure
after filtration. All other chemicals were purchased from
Aldrich and were used as received.
2.4 | X-ray structures of 1, the NiCl2/1
and CoCl2/6 complexes
Colorless single crystals of the compounds (dimensions:
N1,N1,N2,N2-tetrakis[(diphenylphosphino)methyl]ethane-
1,2-diamine (1): 0.35 Â 0.25 Â 0.25 mm, Ni (N,N-bis
((diphenylphosphino)methyl)benzenamine)2Cl2 (NiCl2/
6): 0.31 Â 0.35 Â 0.23 mm, and CoO(N,N-bis((diph-
Gas chromatography (GC): Trace DSQ GC
column = DB-5
ratio = 50:1,
30 m  2.5 mm  0.25 μm,
split
tem-
flow
rate = 1 ml minÀ1
,
inlet
perature = 260ꢁC, column temperature = 50ꢁC (hold for
1 min) then increased to 260 15ꢁC minÀ1 up C at a heating
rate of 15ꢁC minÀ1 up (hold 10 min). GC–MS: Trace DSQ
GC–MS column.
enylphosphino)methyl)benzenamine)2Cl2
(CoCl2/6):
0.39 Â 0.34 Â 0.25 mm) were produced by slow evapora-
tion of the solvents from a solution of the compounds in
hexane/dichloromethane at 25ꢁC. Diffraction data were
collected at room temperature using the φ-scan and
ω-scan technique on a Smart Apex Duo diffractometer
1H, 13C, 29Si and 31P nuclear magnetic resonance
(NMR) spectra were measured using
a
Bruker
AV400-MHz spectrometer operating at 400.13, 100.62,
79.49, and 161.97 MHz, respectively.
with
graphite-monochromated
Mo–Kα
radiation
IR spectra were recorded on a Nicolet 5700 instru-
ment and Elemental analyses were performed on a
VARIO EL-3 elemental analyzer.
(λ = 0.71073 Å). The structures were solved using direct
methods (SHELXTL-PLUS)[31] and subsequent Fourier
difference syntheses, which were then refined by
full-matrix least-squares on F2 (SHELXL-97).[32] All non-
hydrogen atoms were refined anisotropically, while the
hydrogen atoms were placed in their geometrically
idealized positions. Crystal data and details of the struc-
tures are given in Tables 1–3. (Tables 1–3) (Figures 1–3).
2.2 | Synthesis of the N,P-ligands
An oven-dried, 100-ml three-necked flask equipped with
a magnetic stir bar, rubber septum, and reflux condenser
was charged with toluene (40 ml), followed by diamine
(11.0 mmol) or amine (22.0 mmol), and 37% HCHO
(5.3 ml 65.0 mmol) under an Ar atmosphere. After stir-
ring for 5 min, the reaction mixture was heated at 60ꢁC,
and diphenylphosphine (7.5 ml 43.0 mmol) was added at
once. The reaction mixture was heated at 61ꢁC for 1.5–
2 h and then cooled to room temperature. The combined
organic extracts were dried using anhydrous Na2SO4. The
filtrate was concentrated in vacuo and the resulting crude
product purified by recrystallization from ethanol to give
TABLE 1 Single crystal structure data of ligand 1
Empirical formula
Formula weight
Temperature (K)
Space group
Unit cell dimensions
a (Å)
C54H52N2P4CH2Cl2
937.78
296 (2)
P À1
10.062 (4)
1
a yellow solid. The H, 13C, and 31P NMR, infrared (IR),
b (Å)
10.274 (4)
c (Å)
13.358 (6)
and elemental analyses were consistent with those
reported in the literature.[15]
Alpha (deg)
Beta (deg)
75.163 (10)
79.198 (10)
Gamma (deg)
Volume (Å3)
Z, calculated density
81.614 (10)
2.3 | Catalytic hydrosilylation of alkene
with silane
1304.2 (10)
1
Abs. coeff. (mmÀ1
)
0.284
The typical hydrosilylation reaction procedure was as fol-
lows: Given amounts of the catalyst and ligand were
charged into a 10-ml round bottomed flask equipped with
a magnetic stirrer, followed by the alkene and silane. The
resulting mixture was heated to the specified tempera-
ture, and the hydrosilylation reaction was allowed to pro-
ceed with constant stirring for 5 h. At the end of the
F(000)
492
Reflections collected/unique
Goodness-of-fit on F2
4270/5875[R (int) = 0.0505]
1.006
θmax 25.2
Final R indices[I > 2σ(I)]
R indices (all data)
R1 = 0.1329,wR2 = 0.4721
R1 = 0.1535,wR2 = 0.990

LIU ET AL.
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FIGURE 1 Single crystal structure of ligand
1
(or dialkylphosphine). N,P-ligands 1–22 were character-
ized using NMR and IR spectroscopy and elemental
analyses. The structure of ligand 1 was also determined
using X-ray analysis (Figure 1). Furthermore, the NMR,
IR, and elemental analyses data of the compounds were
in agreement with their assigned structures.
TABLE 2 Single crystal structure data of complex NiCl2/6
Empirical formula
Formula weight
Temperature (K)
Space group
Unit cell dimensions
a (Å)
2(C32H29Cl2NNiP2),CH2Cl2
2646.22
293 (2)
P21/c
9.7297 (14)
3.1 | Effect of different metal salts on
the hydrosilylation reaction
b (Å)
13.1974 (18)
c (Å)
26.581 (4)
Alpha (deg)
Beta (deg)
90
A series of different transition metal halides/(CH2N
(CH2PPh2)2)2 (1) were screened in the hydrosilylation
reaction of 1-octene using diphenylsilane. The results
were summarized in Table 4. CuCl2/1, ZnCl2/1, and
TiCl4/1 showed no catalytic activity upon heating at
100ꢁC for 8 h. FeCl2/1 showed low catalytic activity
(ꢀ35.5% conversion of 1-octene). MnCl2/1, CrCl3/1, and
NiCl2/1 showed some catalytic activity. CoCl2/1 showed
the highest catalytic activity (ꢀ >99.9% conversion of
1-octene) under the reaction conditions. Additionally, no
α-adduct, dehydrogenative silylation product and octane
were detected.
106.652 (5)
Gamma (deg)
Volume (Å3)
Z, calculated density
90
3270.0 (8)
1
Abs. coeff. (mmÀ1
)
0.959
F(000)
1364.0
Reflections collected/unique
Goodness-of-fit on F2
5079/7445[R (int) = 0.0500]
1.081
θmax 25.2
Final R indices[I > 2σ(I)]
R indices (all data)
R1 = 0.0826,wR2 = 0.2651
R1 = 0.1250,wR2 = 1.080
A series of different cobalt salts/1 were then exam-
ined in the hydrosilylation reaction of 1-octene using
diphenylsilane. The selectivity of the β-adduct catalyzed
by CoF2/1 or CoBr2/1 was relatively low (89.1% and
78.9%, respectively). No α-adduct, dehydrogenative
silylation product, and octane were detected in the
reaction catalyzed by Co (CH3COO)2/1, Co (BF4)2/1,
and cobalt 2-ethylhexanoate/1, respectively. Although
the selectivity of the reaction catalyzed by cobalt salt/1
3 | RESULTS AND DISCUSSION
A series of highly efficient protocols used for the synthe-
sis of N,P-ligands (1–22) are shown in Scheme 1. These
products (1–22) were synthesized upon the reaction of an
amino compound, formaldehyde, and diphenylphosphine

4 of 11
LIU ET AL.
FIGURE 2 Effect of reaction temperature
and reaction time on the hydrosilylation
reaction of CoCl2/1 complex
(BF4)2/1, and cobalt 2-ethylhexanoate/1, the conversion
of 1-octene was extremely high (close to 100%). There-
fore, after comprehensive consideration, cobalt chloride
was chosen as the catalyst used in our subsequent
experiments.
TABLE 3 Single crystal structure data of complex CoCl2/1
Empirical formula
Formula weight
Temperature (K)
Space group
Unit cell dimensions
a (Å)
C32H29Cl2CoNOP2
635.33
296
P21/c
3.2 | Effect of the different N,P-ligands
9.4662 (5)
on the hydrosilylation reaction
b (Å)
16.8908 (9)
c (Å)
19.3207 (10)
The catalytic properties of CoCl2/N,P-ligands 1–22 in the
hydrosilylation reaction of 1-octene using diphenylsilane
were investigated, and the results are listed in Table 5. By
comparing the data, it was found that the cobalt catalyst
system containing four P-ligands presented excellent cat-
alytic performance in terms of both the conversion and
β-adduct selectivity. However, the product conversion of
the cobalt catalyst system containing a single P-ligand
was generally low; the conversion was only 32.5% when
using CoCl2/15 as the catalyst. At the same time, in
the P-ligands whose groups directly connected to
the nitrogen atoms are phenyl or alkyl groups, the con-
version and selectivity of the reaction were better than
those observed using P-ligands directly connected with a
pyridine ring ligand (Entries 6–9 and 15–17, Table 5).
Moreover, when the group attached to the nitrogen atom
is an alkyl group, the length of the alkyl chain did not
affect the activity of the catalyst (Entries 11–13, Table 5).
In addition, alkyl phosphine was used to replace
Alpha (deg)
Beta (deg)
90
103.541 (1)
Gamma (deg)
Volume (Å3)
Z, calculated density
90
3003.3 (3)
4
Abs. coeff. (mmÀ1
)
0.882
F(000)
1308.0
Reflections collected/unique
Goodness-of-fit on F2
3513/3877[R (int) = 0.5340]
1.014
θmax 25.2
Final R indices[I > 2σ(I)]
R indices (all data)
R1 = 0.0456,wR2 = 0.1237
R1 = 0.0763,wR2 = 1.014
was better, the conversion of 1-octene was different due
to the different counter anions used. The conversion of
1-octene catalyzed by CoBr2/1 was 50.8%, while in the
reactions catalyzed by CoCl2/1, Co (CH3COO)2/1, Co

LIU ET AL.
5 of 11
FIGURE 3 Effect of the amount of complex
CoCl2/1 on the hydrosilylation reaction
SCHEME 1 The synthesis of N,P-ligands
diphenylphosphine in the ligand during the reaction of
1-octene using diphenylsilane catalyzed by CoCl2. The
conversion of 1-octene was 91.9%, and the selectivity of
the β-adduct was ꢀ100%. The activity of the catalyst was
only a minor affected by the groups (phenyl or alkyl)
linked on the phosphine atom (Schemes 2 and 3).
3.3 | The effect of different reaction
conditions on the hydrosilylation reaction
The effects of the reaction temperature and time are
illustrated in Figure 4. It shows that the conversion
of 1-octene increases upon increasing the reaction

6 of 11
LIU ET AL.
TABLE 4 The catalysts consisting of different metal salts/1 used to catalyze the hydrosilylation reaction of 1-octene using diphenylsilane
Select. (%)
Entry
Catalyst
CoCl2/1
Conv. (%)
β
α
/
/
/
/
/
/
/
/
/
/
/
/
/
Octane
Dehydrogenative silylation
1
ꢀ100
83
ꢀ100
ꢀ100
ꢀ100
ꢀ100
71
/
/
/
/
/
/
/
/
/
/
/
/
/
/
2
MnCl2/1
/
3
CrCl3/1
79
/
4
NiCl2/1
72
/
5
FeCl2/1
36
29
/
6
ZnCl2/1
/
/
7
CuCl2/1
/
/
/
8
TiCl4/1
/
/
/
9
CoF2/1
69
89
11
21
/
10
11
12
13
CoBr2/1
51
79
Co (CH3COO)2/1
Co (BF4)2/1
Co(C10H7COO)2/1
ꢀ100
ꢀ100
ꢀ100
ꢀ100
ꢀ100
ꢀ100
/
/
Note: Reaction conditions: 1-Octene (4 mmol), Ph2SiH2 (4.4 mmol), catalyst: metal salts/1 (0.02 mol% with respect to 1-octene), and metal salts:1 = 1:1, 8 h,
100ꢁC.
TABLE 5 Cobalt chloride
Select. (%)
complexes prepared using different
Entry
1
Ligands
Conv. (%)
ꢀ100
ꢀ100
ꢀ100
ꢀ100
ꢀ100
95
β
α
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
Octane
Dehydrogenative silylation
N,P-ligands used to catalyze the
hydrosilylation reaction of 1-octene
using diphenylsilane
1
ꢀ100
ꢀ100
ꢀ100
ꢀ100
ꢀ100
97
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
2
2
/
3
3
/
4
4
/
5
5
/
6
6
3
7
7
91
90
10
24
/
8
8
40
76
9
9
ꢀ100
ꢀ100
ꢀ100
95
ꢀ100
96
10
11
12
13
14
15
16
17
18
19
20
21
22
10
11
12
13
14
15
16
17
18
19
20
21
22
4
94
6
ꢀ100
ꢀ100
85
/
ꢀ100
57
/
15
13
27
12
/
33
87
64
73
88
88
ꢀ100
85
ꢀ100
92
8
92
ꢀ100
ꢀ100
ꢀ100
/
ꢀ100
91
/
/
Note: Reaction conditions: 1-Octene (4 mmol), Ph2SiH2 (4.4 mmol), and catalyst CoCl2/Ligand (0.02 mol%
with respect to 1-octene), 1–13, 20–22: CoCl2/Ligand = 1:1, 14–19: CoCl2/Ligand = 1:2, 8 h, 100ꢁC.

LIU ET AL.
7 of 11
SCHEME 2 N,P-ligands
temperature and prolonging the reaction time. When the
temperature is ≥90ꢁC, a 100% conversion can be obtained
within a suitable reaction time. When the temperature
was 80ꢁC, even if the reaction time is increased, the maxi-
mum conversion was <30%. At 90ꢁC, 100ꢁC, and 110ꢁC,
respectively, the reaction was particularly intense over
the first 2 h with the conversion rapidly reaching >80%.
After 2 h, the reaction rate slowed down, but the conver-
sion continued to increase until the complete conversion
of 1-octene. Taking all things into consideration, the
optimal reaction temperature and time was 100ꢁC and
8 h, respectively.

8 of 11
LIU ET AL.
SCHEME 3 The hydrosilylation reaction
FIGURE 6 Crystal structure of the complex CoCl2/6
FIGURE 4 Crystal structure of the catalyst NiCl2/1
the amount of CoCl2/1 used in the reaction. When the
amount of CoCl2/1 was 0.02 mol% with respect to
1-octene, the reaction conversion was >95%. When the
amount of CoCl2/1 was increased 10-fold, the reaction
conversion increased, but the increase was not obvious.
When the catalyst loading was 0.0001 mol% with respect
to the olefin, nearly 65% of 1-octene was converted in the
reaction. The effects of amounts of CoCl2: ligands were
illustrated in Figure 6. When the amount of CoCl2/1 was
1:1, the reaction conversion was >99.9%.
3.4 | Scope of the hydrosilylation
reaction
The hydrosilylation reactions of a variety of alkenes using
diphenylsilane were performed under the optimized reac-
tion conditions in Table 6. When other alkenes such as
1-butene, 1-hexene, 1-octene, 1-dodecene, 1-tetradecene,
and styrene were used as the substrate, excellent
conversions were obtained using the CoCl2/1 catalyst
system. In addition, good conversions were obtained
when phenylsilane, dimethylphenylsilane, and dip-
henylmethylsilane were used to replace diphenylsilane.
FIGURE 5 Effect of the amount of ligand 1 on the
hydrosilylation reaction
The reactions of 1-octene and diphenylsilane carried
out in the presence of different quantities of CoCl2/1
(2, 0.2, 0.02, 0.002, 0.0002, and 0.0001 mol%) at 100ꢁC
were investigated, and the results shown in Figure 5.
The reaction conversion increased upon increasing

LIU ET AL.
9 of 11
TABLE 6 CoCl2/1 catalyzed
hydrosilylation reaction of different
olefins using silanes
Select. (%)
Entry
Olefin
Silane
Conv. (%)
β
α
/
/
/
/
/
/
/
/
/
Alkane
1
2
3
4
5
6
7
8
9
CH3(CH2)3CH=CH2
CH3(CH2)5CH=CH2
CH3(CH2)7CH=CH2
CH3(CH2)11CH=CH2
CH3(CH2)13CH=CH2
PhCH=CH2
Ph2SiH2
Ph2SiH2
Ph2SiH2
Ph2SiH2
Ph2SiH2
Ph2SiH2
PhSiH3
ꢀ100
ꢀ100
96
ꢀ100
ꢀ100
83
/
/
17
28
36
60
23
30
32
89
72
83
64
66
40
CH3(CH2)5CH=CH2
CH3(CH2)5CH=CH2
CH3(CH2)5CH=CH2
91
77
PhMeSiH2
PhMe2SiH
80
70
75
68
Note: Reaction conditions: Olefin (4 mmol), silane (4.4 mmol), and catalyst CoCl2/1 (0.02 mol% with respect
to the olefin) CoCl2:1 = 1:1, 8 h, 100ꢁC.
3.5 | Mechanism
On the basis of our experimental results, we continued to
study the ways in which the metal salts bind to the
ligands. The single crystal structure of Ni(N,N-bis((diph-
enylphosphino)methyl)benzenamine)2Cl2 (NiCl2/6) was
determined using crystals produced by slow evaporation
of the solvents from the catalyst solution in hexane/
dichloromethane(Figure 5). One Ni atom coordinated to
two N,P-ligands. Different from the coordination mode of
NiCl2 and ligand 6, it was found that when CoCl2 and
SCHEME 4 The synthesis of Ni(N,N-bis((diphenylphosphino)
methyl)benzenamine)2Cl2 and CoO(N,N-bis((diphenylphosphino)
methyl)benzenamine)2Cl2
the N,P-ligand coordinate with one another, one oxygen
atom was inserted between the cobalt and phosphine
SCHEME 5 Mechanism

10 of 11
LIU ET AL.
atoms in the catalysts obtained at the end of the reaction.
The single crystal structure of CoO(N,N-bis((diph-
enylphosphino)methyl)benzenamine)2Cl2 (CoCl2/6) was
also determined (Figure 6). The oxygen atom was easily
inserted between cobalt and ligands.[33] The oxygen atom
did some good to the catalytic hydrosilylation reaction of
alkenes.[8,34,35] We speculate that the insertion of the oxy-
gen atom was beneficial to the catalytic activity of the
cobalt complex catalyst and the catalytic hydrosilylation
reaction of alkenes. A reaction may occur between the
phosphine ligand and the Co metal center, which will
help activate the alkene with the Co-phosphine ligand
stabilizing the intermediate formed. On the basis of our
results, we propose the following reaction mechanism
(Scheme 4) (Scheme 5).
ORCID
Yu Liu https://orcid.org/0000-0002-4480-396X
Jiayun Li https://orcid.org/0000-0001-7800-5686
Ying Bai https://orcid.org/0000-0001-5630-5565
Jiajian Peng https://orcid.org/0000-0002-0254-1164
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4 | CONCLUSIONS
In summary, a series of N,P-ligands (1–22) were
synthesized. FeCl2/1(N1, N1, N2, N2-Tetrakis[(diph-
enylphosphino)methyl]ethane-1,2-diamine) showed low
catalytic activity. MnCl2/1, CrCl3/1, and NiCl2/1 showed
some catalytic activity. The CoCl2/N,P-ligand catalyst
system showed high activity and excellent selectivity
(The selectivity of the β-adduct was ꢀ100%.) in the
hydrosilylation reaction. CoCl2/1 showed the highest
catalytic activity (ꢀ >99.9% conversion of 1-octene).
And the hydrosilylation reaction of alkenes using
diphenylsilane catalyzed using CoCl2 in the presence of
these ligands was investigated. The catalyst complexes
formed using CoCl2 and N,P-ligands 1–22 exhibited high
activity and could catalyze the hydrosilylation reaction of
a range of olefin using a variety of silanes. The conver-
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ACKNOWLEDGMENTS
This work was supported by Zhejiang Provincial
Technologies R&D Program of China (grant
no. 2017C31105) and Natural Science Foundation of
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AUTHOR CONTRIBUTIONS
Liu Yu: Data curation. Jiayun Li: Conceptualization;
data curation. Ying Bai: Formal analysis; resources.
Jiajian Peng: Conceptualization.
DATA AVAILABILITY STATEMENT
The data that support the findings of this study are avail-
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