Acylsilane directed aromatic C-H alkenylations by ruthenium catalysis

Article abstract of DOI:10.1039/C8CC08250B

A ruthenium-catalyzed C-H alkenylation of aroylsilanes with electron-deficient alkenes was developed, using acylsilane as the directing group. The mild reaction conditions enable the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF₃, providing a convenient and highly effective method for the synthesis of styrene derivatives bearing acylsilane. Steroid and heterocycles such as furan and thiophene were also well tolerated. Furthermore, acylsilane was efficiently converted to the corresponding aldehyde or carboxylic acid.

Full text of DOI:10.1039/C8CC08250B

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Acylsilane directed aromatic C–H alkenylations by
ruthenium catalysis†
Cite this: Chem. Commun., 2019,
55, 826
Xiunan Lu,a Cong Shen,a Keke Meng,a Li Zhao,*ab Tingyan Li,a Yaling Sun,a
Jian Zhang *a and Guofu Zhong*a
Received 15th October 2018,
Accepted 14th December 2018
DOI: 10.1039/c8cc08250b
rsc.li/chemcomm
A
ruthenium-catalyzed C–H alkenylation of aroylsilanes with improve the reaction efficiency. Directed C–H activation typically
electron-deficient alkenes was developed, using acylsilane as the proceeds via five- or six-membered cyclometalation processes, using
directing group. The mild reaction conditions enable the tolerance various functionalities as directing groups, such as carboxylate,
of a wide scope of functionalities such as OMe, F, Cl, Br and CF3, amide, alcohol, amine and imine.8,9 There are also reports on
providing a convenient and highly effective method for the synthesis meta-10 and para-selective11 aromatic C–H activation, using a nitrile
of styrene derivatives bearing acylsilane. Steroid and heterocycles embedded in the template that serves as a linear end-on directing
such as furan and thiophene were also well tolerated. Furthermore, group. Unfortunately, the use of DGs often limits broader applica-
acylsilane was efficiently converted to the corresponding aldehyde tions of the developed reactions, since the DGs are usually not an
or carboxylic acid.
integral part of the desired molecules. Recently, considerable
research has hence focused on the development of easily removable
Acylsilanes have been known for long time and their spectral and modified DGs for C–H functionalizations.12
behavior and certain chemical properties have been extensively
Due to the great utility of an acylsilane moiety as well as its
studied. The electron inherent in acylsilane leads to a reactivity versatility in chemical conversions, it is intriguing to develop
profile that is distinct from other carbonyl compounds.1 In the C–H functionalization using such a weakly coordinating acylsilane
past decades, they have emerged as versatile synthetic inter- as a reactant.13 In light of the recent work on acylsilane-directed
mediates for use in a variety of chemical transformations.2 For aromatic C–H amidation by iridium catalysis14a and alkenylation
example, acylsilanes are known to undergo thermally or photo- catalyzed by rhodium,14b it is still highly desirable to extend the
chemically induced 1,2-silicon-to-oxygen migrations (known as approach to ruthenium-catalyzed C–H activation processes for a
the Brook rearrangements) to form siloxycarbenes.3 Furthermore, number of reasons. First, both the substrate and reaction type can
there are reports on cross-coupling reactions using acylsilanes via be complementary to that of the Rh- and Ir-catalyzed C–H function-
C–Si bond cleavage.4 Moreover, acylsilane intermediates have alizations. Second, the conditions used for Rh(III), Ir(III) and Ru(II)
been proven to be useful in complex molecule synthesis.5
are often different, which could offer new opportunities for
Vinyl arenes are valuable intermediates, offering broad appli- developing ligand-controlled, enantioselective and remote C–H
cations in synthetic and materials chemistry.6 Thus, numerous activation reactions. Third, ruthenium complexes are much
aromatic C–H alkenylation reactions have been reported due to high cheaper, which facilitate their potential application in synthetic
atom- and step economy.7 The site-selectivity of C–H activations is chemistry. Given the importance of acylsilane and our continuous
usually achieved using directing groups (DGs), which usually play interest in chelation-assisted C–H activation,15 herein, we focus on
dual roles.8 First, the DG acts as a s-donor ligand to the active the Ru(II)-catalyzed aromatic C–H olefination to address these issues
catalyst and brings the metal in close proximity to the target C–H (Scheme 1). The generality of this approach is also demonstrated by
bond, thus ensuring site-selectivity. Second, DGs can increase the accomplishing C–H olefination of heterocyclic substrates such as
effective concentration of the catalyst at the site of interest to furan and thiophene.
The initial optimization experiments were performed with
a College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal
University, Hangzhou 310036, China. E-mail: lizhao@hznu.edu.cn,
zhangjian@hznu.edu.cn, zgf@hznu.edu.cn
b Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of
Education, Hangzhou Normal University, Hangzhou 311121, China
† Electronic supplementary information (ESI) available: Detailed experimental
procedures analytical data. See DOI: 10.1039/c8cc08250b
benzoylsilane (1a) derived from benzoyl chloride and butyl
acrylate (2a), in the presence of robust and inexpensive [RuCl2(p-
cymene)]215,16 (2.5 mol%) and AgOTf (10 mol%) in DCE at 60 1C as
the catalytic conditions, and the reaction afforded desired vinyl
arene 3aa in 40% yield (Table 1, entry 1). Various silver salts, such
as Ag2O, AgOTFA, Ag2CO3, AgOAc, AgSbF6 and AgBF4, were tested,
826 | Chem. Commun., 2019, 55, 826--829
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(entries 18–20). Moreover, complex Ru( p-cymene)(OAc)2 was also
tested and led to comparable results in the mandatory presence of
AgSbF6 (entries 21 and 22). Interestingly, an iridium complex such as
[IrCp*Cl2]2 also showed limited catalytic activity toward this reaction
(entry 23).14a
With the optimized catalytic conditions in hand, we next
examined the scope of this acylsilane directed aromatic C–H
alkenylation reaction. Various acrylates such as methyl acrylate,
tert-butyl acrylate, benzyl acrylate, phenyl acrylate, methoxyethyl
acrylate and tetrahydrofurfuryl acrylate were all efficiently reacted
with benzoylsilane (1a) to produce the corresponding styrenes in
good to excellent yields with excellent regio- and stereo-selectivities
(Table 2, 3aa–3ag). Intriguingly, ethyl vinyl ketone 2h reacted well
with 1a, affording the expected product 3ah in moderate yield.
Styrene was also a suitable coupling partner, affording stilbene 3ai
in 61% yield. Moreover, styrenes bearing a trifluoromethyl group
led to better results (3aj and 3ak). Some other electron-deficient
alkenes were also tested, and both phenyl vinyl sulfone and diethyl
vinylphosphonate reacted smoothly (3al and 3am). The structurally
complex steroid analogue 3an could also be obtained by such
acylsilane directed C–H activation, exhibiting high chemo-
selectivity and good functionality tolerance. Although acrylic
acid showed limited reactivity, 2-hydroxyethyl acrylate led to
excellent yield (3ao and 3ap).17
Scheme 1 Acylsilane directed aromatic C–H alkenylation by ruthenium
catalysis.
Table 1 Optimization of catalytic conditionsa
Entry
Additive
Oxidant
Solvent
Yieldb (%)
1
2
3
4
5
6
7
8
AgOTf
Ag2O
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2ÁH2O
Cu(OTf)2
Cu(OAc)2
Cu(OAc)2
—
DCE
DCE
DCE
DCE
DCE
DCE
DCE
CHCl3
DCM
DME
MeCN
THF
DMF
Toluene
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
40
NR
o5
NR
NR
41
23
15
39
0
AgOTFA
Ag2CO3
AgOAc
AgSbF6
AgBF4
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
—
The scope of the cross-coupling of differently substituted
aroylsilanes 1 was also investigated (Table 3). Functional
9
10
11
12
13
14
15c
16c
17c
18
19d
20
21e
22e
23f
0
Table 2 Substrate scope for alkenylation of benzoylsilanea
o5
0
0
79
49
0
0
0
0
73
0
AgSbF6
AgSbF6
AgSbF6
—
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
AgSbF6
25
a
Unless otherwise noted, the reactions were carried out using acylsilane (1a,
0.20 mmol), alkene (2a, 0.40 mmol), [RuCl2(p-cymene)]2 (2.5 mol%), additive
(10 mol%), and oxidant (1.2 equiv.) in a solvent (0.2 M, 1.0 mL) at 60 1C for
24 h under an argon atmosphere (1 atm). b The yields indicated in the table
are isolated yields. c 5 mol% [RuCl2(p-cymene)]2 was used. d Without
[RuCl2(p-cymene)]2. e 10 mol% Ru( p-cymene)(OAc)2 was used instead of
[RuCl2(p-cymene)]2. f 5 mol% [IrCp*Cl2]2 was used instead of [RuCl2(p-
cymene)]2. DCE = 1,2-dichloroethane and DME = 1,2-dimethoxyethane.
and only AgSbF6 showed comparable results (entries 2–7). Replacing
the DCE by DCM and chloroform even led to worse results (entries 8
and 9). Meanwhile, commonly used solvents such as DME, MeCN,
THF, DMF and toluene greatly hindered the reaction (entries 10–14),
showing the remarkable solvent effect in such a reaction. Much
to our delight, increasing the amount of [RuCl2(p-cymene)]2 to
5.0 mol% led to 79% product yield (entry 15). Furthermore, other
copper salts such as Cu(OTf )2 and Cu(OAc)2ÁH2O did not promote
the reaction (entries 16 and 17). Control experiments carried out
have validated the mandatory presence of a ruthenium catalyst, silver
a
Unless otherwise noted, the reactions were carried out using acylsilane
(1a, 0.20 mmol), alkene (2a, 0.40 mmol), [RuCl2( p-cymene)]2 (5.0 mol%),
AgSbF6 (10 mol%), and Cu(OAc)2 (1.2 equiv.) in DCE (1.0 mL) at 60 1C for
additive, and copper salt to provide the cross-coupling product 24 h under an argon atmosphere (1 atm). The yields are isolated yields.
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Table 3 Substrate scope of aroylsilanesa
Scheme 2 Competition/deuterium-labeled experiments.
aroylsilanes were subjected to standard conditions in the presence
of D2O or CD3COOD, H/D scrambling was observed both in 1b and
product 3aa, showing a reversible C–H cyclometalation event
(Scheme 2c and d). Moreover, a considerable intermolecular kinetic
isotope effect (KIE) of 2.4 and an intramolecular KIE of 1.1 were
observed (Scheme 2e and f ). These data indicated that the C–H
metalation was unlikely the rate-determining step.18
a
Unless otherwise noted, the reactions were carried out using acylsilane
(1a, 0.20 mmol), alkene (2a, 0.40 mmol), [RuCl2( p-cymene)]2 (5.0 mol%),
AgSbF6 (10 mol%), and Cu(OAc)2 (1.2 equiv.) in DCE (1.0 mL) at 60 1C for
24 h under an argon atmosphere (1 atm). The yields are isolated yields.
groups such as Me, OMe, COOMe and even CF3 attached to the
para-position of the phenyl ring were all tolerated, regardless of
their electron-withdrawing or electron-donating properties (Table 3,
3ba–3ea). Sensitive and valuable functional groups such as F, Cl, or
Br could also be well tolerated, without any decrease in product
yields, indicating the great synthetic value of this protocol (3fa–3ia).
Notably, though meta-substituted aroylsilanes reacted well with
acrylate, ortho-substituted benzoylsilane showed very limited
reactivity due to steric hindrance (3ia–3ka). However, aroylsilane
bearing a nitrile group was totally inactive presumably due to
the strong coordination to the metal center. Incorporation of a
large aromatic ring such as naphthalene also led to good yield
as well as excellent regio-selectivity (3la). Intriguingly, hetero-
cycles such as furan and thiophene were also suitable, affording
the corresponding products 3ma and 3na in moderate yields.
We also conducted inter-molecular competition experiments
using differently substituted aroylsilanes 1 and alkenes 2. Alkenyla-
tion of aroylsilanes 1c and 1e with alkene 2a in a one-pot fashion
exhibited an electron-rich substrate to be preferentially converted,
which is in good agreement with an electrophilic activation mani-
fold, like in the Ru-catalyzed aromatic C–H alkenylation directed by
the carbonyl group (Scheme 2a).9,16 In contrast, the competition
experiments of acrylate 2b and ketone 2h with aroylsilane 1a under
optimal conditions revealed that the acrylate coupling partner
reacted preferentially (Scheme 2b). Considering the remarkable
activity of the cationic ruthenium(II) catalyst, we became interested
in probing its mode of action in the alkenylation reactions. When
When exposed to visible-light irradiation, the ortho-olefinated
acylsilanes underwent an intramolecular cyclization to afford
indanone derivatives.14b To demonstrate the further utility of our
acylsilane directed C–H olefination, we attempted elaboration of
the alkenylated product 3 (Scheme 3). Treatment of benzoyltri-
methylsilane 3aa with one equivalent of KF in a mixed solvent
EtOH/H2O (v/v = 3/1) at 50 1C for 16 hours gives the corresponding
benzaldehyde 4 in 65% isolated yield (Scheme 3a). Meanwhile,
acylsilane 3aa could also be smoothly converted to carboxylic acid
5 in 73% yield, promoted by a simple Fe(NO3)3 salt (Scheme 3b).
This result paves the way for the development of new transfor-
mations involving acylsilane intermediates.
Plausible mechanisms are illustrated in Scheme 4. First,
reversible acetate-assisted C–H metalation of 1 takes place to
give a five-membered ruthenacycle intermediate I accompanied
Scheme 3 Synthetic applications.
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We gratefully acknowledge the National Natural Science
Foundation of China (NSFC) (21502037 and 21672048), the Natural
Science Foundation of Zhejiang Province (ZJNSF) (LY19B020006 and
LY18E030005), the Social Development Program of Hangzhou
Science and Technology Bureau (20180533B01), the Open Founda-
tion of MOE Key Laboratory of Macromolecular Synthesis and
Functionalization (2018MSF), the Open Foundation of Collaborative
Innovation Centre for Manufacture of Fluorine and Silicone Fine
Chemicals and Materials (FSi2018A026), and the Pandeng Plan
Foundation of Hangzhou Normal University for Youth Scholars of
Materials, Chemistry and Chemical Engineering for financial sup-
port. G. Z. acknowledges a Qianjiang Scholar award from Zhejiang
Province, China.
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