A pronounced ligand effect on platinum-catalyzed Hydrosilylation of terminal alkynes

Article abstract of DOI:10.1002/aoc.4037

The use of ligands to tune the reactivity and regioselectivity of transition metal-based catalyst for silicon-mediated organic synthesis (SiMOS) is an important topic and challenge in organosilicon chemistry and synthetic organic chemitstry. In this manus

Full text of DOI:10.1002/aoc.4037

Received: 15 May 2017
DOI: 10.1002/aoc.4037
Revised: 18 July 2017
Accepted: 19 July 2017
C O M M U N I C A T I O N
A pronounced ligand effect on platinum‐catalyzed
Hydrosilylation of terminal alkynes
Cheng Dong1 | Yang Yuan1 | Yu‐Ming Cui1 | Zhan‐Jiang Zheng1
Li‐Wen Xu1,2
| Jian Cao1 | Zheng Xu1 |
1 Key Laboratory of Organosilicon
The use of ligands to tune the reactivity and regioselectivity of transition metal‐
Chemistry and Material Technology of
Ministry of Education, Hangzhou Normal
University, No 1378, Wenyi West Road,
Science Park of HZNU, Hangzhou, China
2 State Key Laboratory for Oxo Synthesis
and Selective Oxidation, Suzhou Research
Institute of LICP, Lanzhou Institute of
Chemical Physics (LICP), Chinese
Academy of Sciences, China
based catalyst for silicon‐mediated organic synthesis (SiMOS) is an important
topic and challenge in organosilicon chemistry and synthetic organic
chemitstry. In this manuscript, the dual ligand platinum catalyst system was
developed for the hydrosilylation of alkynes. It was found that regioselectivity
enhancement was determined with combinational use of phosphine ligand
(6a) and multifunctional Py‐BINMOL ligand (4a). The corresponding
vinylsilanes were obtained in high yields and high regioselectivities.
Correspondence
Zhan‐Jiang Zheng, Key Laboratory of
Organosilicon Chemistry and Material
Technology of Ministry of Education,
Hangzhou Normal University, No 1378,
Wenyi West Road, Science Park of HZNU,
Hangzhou, P.R. China.
KEYWORDS
alkyne, homogeneous catalysis hydrosilylation, phosphine ligand, platinum
Email: zzjiang78@hznu.edu.cn
Li‐Wen Xu, State Key Laboratory for Oxo
Synthesis and Selective Oxidation, Suzhou
Research Institute of LICP, Lanzhou
Institute of Chemical Physics (LICP),
Chinese Academy of Sciences, P. R. China.
Email: liwenxu@hznu.edu.cn
Funding information
Natural Science Foundation of Zhejiang
Province, Grant/Award Number:
LY16E030009, LY17B030005 and
LY17E030003; National Natural Science
Foundation of China, Grant/Award Num-
ber: 21472031 and 21503060; Science and
Technology Department of Zhejiang Prov-
ince, Grant/Award Number: 2015C31138
Organosilicon compounds are of special interest due to
their wide application in organic and advanced materials
chemistry. Recently, catalytic hydrosilylation of carbonyl
compounds[1] and unsaturated carbon–carbon bonds has
been extensively developed in the past decade,[2] which
has been proved to be a facile process to obtain structur-
ally diverse organosilicon compounds and related organic
molecules. Among versatile hydrosilylation reactions, the
metal‐catalyzed hydrosilylation of terminal alkynes is
arguably one of the most straightforward processes for
the synthesis of vinyl‐containing organosilicon com-
pounds. These important building blocks can be applied
in numerous transformations and material synthesis,
including cross‐coupling reaction, and nucleophilic
Appl Organometal Chem. 2017;e4037.
wileyonlinelibrary.com/journal/aoc
Copyright © 2017 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4037

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DONG ET AL.
additions as well as desilylation reactions.[3] In the past
few years, rapid and considerable progress in catalytic
hydrosilylation of alkynes has been made by several
groups.[4–6] However, most of metal catalysts are inher-
ently difficult in controlling the low reactivity as well as
regio‐ and stereo‐selectivity in the hydrosilylation of ter-
minal alkynes with organohydrosilanes. Therefore, it is
of great importance to develop a new catalyst system for
the hydrosilylation of alkynes to synthesis of vinylsilanes,
as it will open up a simple process to synthesize structur-
ally diverse organosilicon compounds with good
regioselectivity.
used, affording 2a/3a in moderate regioselectivity in most
of cases. Fortunately, it was found that Xing‐Phos is a
good ligand (Entry 21). In addition, the combinational
use of 6a and 4a gave better selectivity for this reaction
at room temperature (Entry 24). On the basis of present
findings, we supposed that self‐assembly of multifunc-
tional Py‐BINMOL 4a and amide‐derived phosphine (6a)
could be occurring, resulting in the enhancement of cata-
lyst selectivity of hydrosilylation. In the past decades,
chemist have demonstrated that reaction rate would be
increased more greatly than that with either catalyst alone
when more than one catalysts were designed to speed up a
certain reaction.[11] For example, much effort has been
made in creating combinational designer catalysts system
in numerous reactions, such as Shibasaki's bimetallic sys-
tem,[12] Yamamoto's ‘designer acids',[13] Trost's bizinc
complexes,[14] and the combinational use of
organoctalysts and metal catalysts, etc.[15] In contrast to
wide applications of dual catalysis for versatile organic
transformations, the exploring and utilization of dual
ligand for construction of single metal‐centered coopera-
tive systems and its application in organic synthesis is still
in its infancy. In 2015, Shi and Sun developed a series of
dual ligand Zn catalysts for the synthesis of propylene car-
bonate (PC) from epoxide and CO2.[16] The dual phos-
phine and N‐donor ligands showed synergistic effect,
which leading to remarkable enhancement of the cata-
lytic performance. It is attractive topic recently that the
combinational use of two ligands in transition metal catal-
ysis, which would be recognized as a promising way to
overcome the limitations inherently came from metal
center.
Utilizing the K2PtCl4 as the precatalyst, we examined
the alkyne scope of this hydrosilylation reaction
(Table 2). Under the optimized conditions using 4a and
6a as mixed dual ligand, a variety of alkynes bearing dif-
ferent substituents on the phenyl ring underwent the
hydrosilylation reaction with triethylsilane to afford the
corresponding vinylsilanes in high yields with excellent
regioselectivities (see Table 2, Entries 1–8). The platinum
catalyst system derived from the combined use of 4a and
6a enabled the hydrosilylation of aromatic alkynes with
triethylsilane as an assembled model, providing the corre-
sponding vinylsilanes with high regioselectivity. How-
ever, when alkynes 1i‐1 l bearing amine, ester or sulfur
groups were used, no reaction took place. These results
possibly due to the sensitive and fragile assembly between
the ligands and the Pt center, which was destroyed by the
functional group of substrates 1i‐1 l. Notably, the conver-
sion of such reaction is quite good in most of cases (1a‐
1 h) and the combined use of 4a and 6a was also proved
to be an effective strategy in comparison to that with only
6a as single ligand in this reaction because the mixed dual
Meanwhile, owing to its high catalytic performance,
platinum complexes, such as Karstedt catalyst.[7] are by
far the most‐developed metal catalysts for the
hydrosilylation of alkynes and alkenes.[8] Herein, inspired
by previous reports on the catalytic hydrosilylation by
platinum catalysis, we reported our effort to develop phos-
phine ligand –based platinum catalyst systems for
hydrosilylation of alkynes, in which the effect of several
additives, such as Ar‐BINMOLs, on the general plati-
num‐catalyzed hydrosilylation of alkynes was initially
carried out, and finally a new example on the regio‐ and
chemoselective hydrosilylation of terminal alkynes.
Recently, the optically pure 1,1′‐binaphthalene‐2‐a‐
arylmethanol‐2′‐ols (Ar‐BINMOLs) were developed by
our group from simple axial chiral monoalkylated
BINOLs via an asymmetric [1,2]‐Wittig rearrangement.[9]
The Ar‐BINMOLs were found to be effective ligands in
several transition‐metal catalyzed reactions.[9] Owing to
its steric and electronic effect features, we tried to study
its possible ability as a ligand for the Pt catalyzed
hydrosilylation reaction. To begin this study, we first eval-
uated the capacity of various Ar‐BINMOL‐derived multi-
functional ligands, P‐Phosphines as well as other olefin
ligands to mediate the platinum‐catalyzed hydrosilylation
of phenylacetylene with triethylsilane (Table 1). The reac-
tion was initially carried out in the presence of 0.5 mol%
Pt catalyst (Karstedt catalyst, Pt2(dba)3, (PPh3)2PtCl2, or
K2PtCl4) and 1 mol% ligand or co‐ligand in toluene at
60 °C to afford the corresponding products 2a and 3a (see
Table 1). It was found that all of the platinum salts, were
effective under ligand‐free conditions (Entries 1, 11, and
17) without formation of the cis‐vinylsilane products and
the dehydrogenative silylation products. However, the
regioselectivity is varied from 4.7:1 to 24:1. These findings
promoted us to investigate the ligand effect on the plati-
num‐catalyzed hydrosilylation of alkyne 1a. As shown in
Table 1, we screened numerous Ar‐BINMOL‐based multi-
functional ligands[9] and our bifunctional phosphine
ligands (For example, Tao‐Phos and Xing‐Phos).[10]
Unfortunately, no obvious enhancement in the regio‐
and reactivity was observed when these ligands were

DONG ET AL.
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TABLE 1 Ligand screen of platinum (0)‐catalyzed hydrosilylation
of phenylacetylene with Et3SiH in the presence of multifunctional
ligands (4–6)a
TABLE 1 (Continued)
Entry
Pt cat.
Co‐Ligand
2a:3ab
Yield (%)c
18
K2PtCl4
4a
−
Trace
94
Entry
Pt cat.
Co‐Ligand
2a:3ab
Yield (%)c
19
K2PtCl4
K2PtCl4
K2PtCl4
K2PtCl4
K2PtCl4
K2PtCl4
K2PtCl4
K2PtCl4
K2PtCl4
4d
5:1
1
Karstedt Cat.
−
24:1
95
20
5a
4.6:1
50:1
37:1
42:1
75:1
7.5:1
−
92
2
Karstedt Cat.
Karstedt Cat.
Karstedt Cat.
Karstedt Cat.
Karstedt Cat.
Karstedt Cat.
Pt2(dba)3
4a
5.6:1
7.4:1
4.7:1
4.9:1
−
95
21
6a
95
3
4b
95
22
6b
97
4
4c
95
23
6a + 4a
6a + 4a
6a
92
5
4d
95
24[d,e]
25[d,e]
26d
27f
90
6
PPh3
4e or 4f
4a
N.R.
N.R.
94
<10
N.R
92
7
−
6a
8
4.5:1
3.9:1
−
6a + 4a
42:1
9
Pt2(dba)3
4b
94
Note:
10
11
12
13
14
15
16
17
Pt2(dba)3
4e
N.R.
96
aReaction conditions: Phenylacetylene (1 mmol), Et3SiH (1 mmol), platinum
complex (0.5 mol%), Ligand (1 mol%), toluene (2 ml). Reaction time is
12 hours for every case. N.R is no reaction; trace represented <5% yield.
bDetermined by NMR and confirmed by GC–MS analysis.
cTotal yields of isolated product.
dAt room temperature.
(PPh3)2PtCl2
(PPh3)2PtCl2
(PPh3)2PtCl2
(PPh3)2PtCl2
(PPh3)2PtCl2
(PPh3)2PtCl2
K2PtCl4
−
9.2:1
11.4:1
−
4a
96
4b
N.R.
91
4d
6.4:1
−
4e
N.R.
Trace
95
eIn Et2O, for 4 days.
fAt 80 °C.
5b
−
−
4.7:1
(Continues)
ligand system gave better regioselectivity of 2/3 for every
case. Especially for the 1‐ethyl‐4‐ethynylbenzene (1e)

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DONG ET AL.
TABLE 2 Substrate scope of platinum‐catalyzed hydrosilylation of alkynes with Et3SiH in the presence of 4a and 6a as mixed liganda
6a
With 4a and 6a
Entry
alkyne
Yield (%)b
Ratio of 2/3c
Yield (%)b
Ratio of 2/3c
1
92
37:1
92
42:1
2
3
4
90
87
88
39:1
32:1
42:1
91
87
87
52:1
48:1
44:1
5
6
88
89
1:1
2:1
88
86
22:1
21:1
7
8
80
81
31:1
23:1
80
83
43:1
40:1
9
N.R.
N.R.
N.R.
N.R.
10
(Continues)

DONG ET AL.
5 of 6
TABLE 2 (Continued)
6a
With 4a and 6a
Entry
alkyne
Yield (%)b
Ratio of 2/3c
Yield (%)b
Ratio of 2/3c
11
N.R.
N.R.
12
N.R.
N.R.
aReaction conditions: K2PtCl4 (0.005 mmol), amide phosphine ligand 4a or the combinational use of 4a and 6a respectively (0.01 mmol), alkyne (1 mmol), and
Et3SiH (1.1 mmol), in toluene (2 ml) at 80 °C for 12 h.
bTotal yields of isolated product.
cDetermined by NMR and confirmed by GC–MS analysis.
and 1‐ethynyl‐4‐propylbenzene (1f), the ratio of 2e/3e or
2f/3f could be increased from 1:1 or 2:1 to 22:1 or
21:1 respectively. Further comparison experiments
showed that when Karstedts catalyst was used only,
the reaction of 1e or 1f with triethylsilane offered a
mixture of 2e/3e (4.5:1) or 2f/3f (4.8:1) respectively.
The special enhancement of regioselectivity supported
that the assembled use of multifunctional Py‐BINMOL
4a and amide‐derived phosphine (6a) played unex-
pected activation in platinum‐catalyzed hydrosilylation
of terminal alkyne. Although the true reason is not
clear at present, we suggested that the assembled coor-
dination would be a possible mode for this platinum
catalysis. Unfortunately, the crystal structure is not
available from the platinum complex.
In summary, we have determined successfully that the
combined use of multifunctional Py‐BINMOL and amide‐
derived phosphine in platinum‐catalyzed hydrosilylation
of terminal alkyne could be applied in the enhancement
of regioselectivity of hydrosilylation. The platinum‐
catalyzed hydrosilylation of alkynes resulted in high
regioselectivity as well as high‐yield construction of
various vinylsilanes. Further studies, such as the detailed
mechanism of ligand‐controlled platinum‐ catalyzed
hydrosilylation as well as dual ligand effect, are underway
in our group and will be reported in near future.
ACKNOWLEDGEMENTS
This project was supported by the National Natural Sci-
ence Foundation of China (No. 21472031, and 21503060),
Science and Technology Department of Zhejiang Province
(2015C31138). This work is also supported partially by
Natural Science Foundation of Zhejiang Province
(LY17E030003, LY16E030009 and LY17B030005).
ORCID
Zhan‐Jiang Zheng http://orcid.org/0000-0002-1901-6147
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SUPPORTING INFORMATION
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How to cite this article: Dong C, Yuan Y, Cui Y‐
M, et al. A pronounced ligand effect on platinum‐
catalyzed Hydrosilylation of terminal alkynes. Appl
Organometal Chem. 2017;e4037. https://doi.org/
10.1002/aoc.4037
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