Visible-light-induced thiotrifluoromethylation of terminal alkenes with sodium triflinate and benzenesulfonothioates

Article abstract of DOI:10.1039/c7cc03520a

An unconventional reductive quenching cycle was developed to realize the visible-light-induced thiotrifluoromethylation of terminal alkenes. CF₃SO₂Na was used as an easy to handle CF₃ radical source to afford the desired products in moderate to good yields. Mild reaction conditions and a broad substrate scope feature in this transformation.

Full text of DOI:10.1039/c7cc03520a

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DOI: 10.1039/C7CC03520A
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Visible-Light-Induced Thiotrifluoromethylation of Terminal
Alkenes with Sodium Triflinate and Benzenesulfonothioates
Received 00th January 20xx,
Accepted 00th January 20xx
Weiguang Kong, Hejun An and Qiuling Song*
DOI: 10.1039/x0xx00000x
www.rsc.org/
An unconventional reductive quenching cycle was developed to
realize the visible-light-induced thiotrifluoromethylation of
terminal alkenes. CF3SO2Na was used as an easy handled CF3
radical source to afford the desired products in moderate to good
yields. Mild reaction conditions and broad substrate scope
featured this transformation.
Due to its high efficiency in the preparation of
polyfunctionalized compounds and valuable building blocks for
natural
and
biologically
active
compounds,
the
difunctionalization of alkenes, which involves the installation
of two functional groups across a double bond, has received
increasing attention in organic synthesis.1 Meanwhile, it is
well-known that the introduction of trifluoromethyl group (CF3)
can significantly alter the physical, chemical, and biological
properties of the parent compounds.2 Thus, the
difunctionalization of alkenes along with the formation of a
new C-CF3 bond has become an important area and much
effort has been devoted into it with the aim of developing
novel and efficient methods.3
Scheme 1. Visible-Light-Induced Difunctionalization of
Alkenes Involving the Formation of C-CF3 Bonds.
5d, 9
(Scheme 1)
with CF3I, CF3SO2Cl, Umemoto’s reagent or
Togni’s reagents as a CF3 radical source. Despite the success of
these reactions, some issues still get on with these reagents
such as the difficult handling of CF3I (gas), the corrosive and
volatile property of CF3SO2Cl and the high cost of Umemoto’s
Recently, the visible light induced photocatalysis using
photocatalysts to activate organic molecules has been
established as a powerful strategy for triggering new chemical
reactions in organic synthesis with a host of attractive features, reagent and Togni’s reagents. Therefore, a convenient, easy-
handling and cheaper CF3 radical source is highly desirable.
Consideration from the aspect of mechanism, all of these
photoredox-catalyzed alkene difunctionalizations involving
construction of a C−CF3 bond experienced an oxidative
quenching cycle, e.g. a nucleophile was needed to attack the
newly generated carbocation to finish the cycle (Scheme 2, left,
red cycle). We envisage that if a reductive quenching cycle is
possible by selecting appropriate CF3 radical source,
electrophile and photoredox catalyst, the product that
couldn’t be accessible through oxidative quenching cycle might
be obtained (Scheme 2, right, blue cycle). Herein, we report
the visible-light-induced thiotrifluoromethylation of terminal
alkenes with sodium triflinate (CF3SO2Na, Langlois reagent,
white solid) as an easy handled CF3 radical source and benzen
sulfonothioates as a sulfur source. This transformation is
believed to undergo a reductive quenching cycle.
such as mild and environmentally benign reaction conditions,
excellent functional group tolerance, and high reactivity.4 By
applying
this
ideal
protocol,
photoredox-catalyzed
difunctionalization of alkenes along with the formation of a
C−CF3 bond has been extensively studied and great progress
has been achieved including halotrifluoromethylation,5
oxytrifluoromethylation,6
aminotrifluoromethylation,7
carbotrifluoromethylation8 and thiotrifluoromethylation
Institute of Next Generation Matter Transformation, College of Chemical
Engineering, College of Materials Science & Engineering, Huaqiao University, 668
Jimei Blvd, Xiamen, Fujian, 361021, P. R. China.
E-mail: qsong@hqu.edu.cn.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
To achieve our goal of photoredox-catalyzed alkene
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Table 1. Optimization of Thiotrifluoromethylation of Terminal
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DOI: 10.1039/C7CC03520A
Alkenes.a
Scheme 2. The Mechanism of Visible-Light-Induced Di-
functionalization of Alkenes.
a
Reaction conditions: 1a (0.2 mmol), 2a (0.3 mmol), CF3SO2Na (0.3 mmol),
b
d
photocatalyst (2.5 mol%), solvent (2 mL), rt. GC yield. c Isolated yield. No
difunctionalizations along with the formation of a C−CF3 bond
through a reductive quenching cycle, two challenges should be
overcome. Firstly, the oxidation potential of excited state of
photoredox catalyst should be high enough to oxidize
CF3SO2Na (Eox = 1.05 V vs. SCE, CF3SO2K) into CF3 radical,10
more importantly, the reduced form of photoredox catalyst
should have robust reducing power to reduce the carbon
radical generated from the addition of CF3 radical on alkene
into carbanion. According to the redox property of
Ir[dF(CF3)ppy]2(dtbbpy)PF6 [E1/2red (*IrIII/IrII) = +1.21 V, E1/2red
(IrIII/IrII) = -1.37 V vs. SCE], it would meet the requirements of
these two aspects.11 Secondly, in order to avoid the
competitive protonation reaction, choosing an appropriate
electrophile with enough reactivity toward the carbanion
intermediate is critically important. Benzenesulfonothioates
are electrophiles of this kind, they are easily attacked by a
nucleophile due to the good leaving property of
benzenesulphinate, with the pKa of phenylsulfinic acid being
2.76. 12
light. e 1: Ir[dF(CF3)ppy]2(dtbbpy)(PF6), 2: Ir[dF(CF3)ppy]2(bpy)(PF6).
Simple terminal alkenes (3aa-3fa) exhibited robust reactivity in
this transformation and all of the corresponding products were
obtained in good yields. Notably, the synthetic useful epoxide
group was well compatible in the reaction (3ag). Phenyl allyl
ethers were competent candidates in the reactions, and they
were smoothly thiotrifluoromethylated in 50-61% yields with
different para-substituted groups such as -Me, - OMe, -F, -Cl, -
Br, -CH2CN and -NHCOMe (3ha
dimethylbenzene and 2-(allyloxy)naphthalene gave inferior
results (3pa 3qa) probably owing to the steric hindrance and
-3oa), however, 2-(allyloxy)-1,3-
,
low reactivity. (But-3-en-1-yloxy)benzene, 1-(vinyloxy)butane
and but-3-en-1-yl(p-tolyl)sulfane could also give the desired
products in moderate yields (3ra-3ta). It should be noted that
terminal alkene with a -OH group could successfully undergo
Table 2. Scope of the Terminal Alkenes.
Under this context, we chose allylbenzene (1a), S-phenyl
benzenesulfonothioate (2a), CF3SO2Na as the model substrates
and Ir[dF(CF3)ppy]2(dtbbpy)PF6 as photoredox catalyst to
conduct our initial studies (Table 1). To our delight,
thiotrifluoromethylation product (3aa) was obtained in 76%
isolated yield after irradiating a reaction mixture composed of
1a (0.2 mmol), 2a (0.3 mmol), CF3SO2Na (0.3 mmol) and
Ir[dF(CF3)ppy]2(dtbpy)PF6 (1) (2.5 mol%) in anhydrous CH3CN
for 18 h (Table 1, entry 1). It should be noted that no
protonation byproduct was detected by GC-MS under this
reaction conditions. Ir[dF(CF3)ppy]2(bpy)(PF6) (2) could also
promote the reaction yet with somewhat lower yield (entry 2).
Further screening of solvents revealed that CH3CN was still the
best choice (entry 1, 3-8), using other solvents not only led to
the decrease in yields but also increased the amount of
protonation byproduct. Control experiments found that light
and photoredox catalyst were essential for the reactions, the
reaction did not proceed either without irradiation (entry 9) or
in the absence of the photocatalyst (entry 10).
With the optimized conditions in hand, we set out to
explore the substrate scope of the reaction with a range of
different terminal alkenes (Table 2). It was demonstrated that
this reaction showed good functional group compatibility.
Reaction conditions:
mmol), photocatalyst (2.5 mol%), CH3CN (2 mL), rt, 18 h.
1 (0.2 mmol), 2a (0.3 mmol), CF3SO2Na (0.3
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standard conditions was also measured according to the
thiotrifluoromethylation without formation of the protonation
side product (3ua). In addition, 1-phenylpent-4-en-1-one could
give the desired products in 65% yields (3va). Moreover, the
nitrogen-containing groups such as phthaloyl and carbazolyl
were also well tolerated in the reaction, and the desired
products were obtained in moderate to good yields (3wa-3ya).
In the case of carboxylic ester, sulfonate and 4-(but-3-en-1-
yloxy)-2H-chromen-2-one, the corresponding desired products
View Article Online
reported procedure (for details, see Supporting Information),
DOI: 10.1039/C7CC03520A
14
its value was Φ = 0.142, which indicated that radical chain
process was theoretically ruled out in this visible-light-induced
thiotrifluoromethylation of terminal alkenes. All of these
results confirmed our hypothesis that this visible-light-induced
thiotrifluoromethylation of terminal alkenes with CF3SO2Na
and benzenesulfonothioates undergoes a reductive quenching
cycle.
were obtained in moderate to good yields (3za
We next examined the substrate scope of this
transformation with respect to different
-3§a).
benzenesulfonothioates (Table 3). It was found that a variety
of S-aryl benzenesulfonothioates could be used to participate
in this visible-light-induced thiotrifluoromethylation of
terminal alkenes. Generally, functional groups such as -Me, -
OMe, -F, -Cl, -Br could be well tolerated to give the desired
products in moderate to good yields without the influence of
the position of functional groups (3ab-3ae, 3ag-3ai). Moreover,
benzenesulfonothioates with sensitive group –NO2 and pyridyl
could also give the products in satisfied yields (3af, 3aj).
However, for S-alkyl benzenesulfonothioates, the reactions
Scheme 3. Experimental Probes on Reaction Mechanism
Gratifyingly, the reaction could be readily scaled up without
loss of its efficiency, 296 mg (50% yield) of
thiotrifluoromethylation product 3aa was obtained in 2 mmol
scale (Scheme 4, eq 1). The practicability of the reaction was
further demonstrated by applying it into the modification of (-
)-Borneol derivative 1ß and estrone derivative 1&, the desired
thiotrifluoromethylaed products 3ßa and 3&a were obtained
in 44% and 41% yield respectively (Scheme 4, eq 2 and 3). The
products of this thiotrifluoromethylation reaction could also
be transformed into its sulphone derivatives under mild
condition. As an example, 5a was obtained in 84% yield
(Scheme 4, eq 4).
became unreactive (3ak-3am) probably due to the weak
eletrophilicity of S-alkyl benzenesulfonothioates. Several
experiments were conducted to gain insight into the
mechanism of the reaction (Scheme 3). When radical
scavenger (BHT or TEMPO) was added, the reaction was totally
Table 3. Scope of the Benznenesulfonothioates.
In
summary,
a
novel
visible-light-induced
thiotrifluoromethylation of terminal alkenes with sodium
triflinate and benzenesulfonothioates has been developed.
The mechanistic studies suggested that this reaction
undergoes an untraditional reductive quenching cycle.
CF3SO2Na was used as an easy-handled and cheaper CF3 radical
Reaction conditions: 1a (0.2 mmol),
2 (0.3 mmol), CF3SO2Na (0.3
mmol), photocatalyst (2.5 mol%), CH3CN (2 mL), rt, 18 h.
suppressed (eq 1), which suggested that a SET pathway was
involved in this transformation. Next when ethene-1,1-
diyldibenzene was added to the reaction under the standard
conditions, radical addition elimination product 4a and radical
addition protonation product 4b were afforded in overall 42%
yield (eq 2), this radical-trapping experiment clarified the
formation of CF3 radical in this thiotrifluoromethylation
process. It was reported that disulphide could be attacked by a
13
radical to form a C-S bond,
however, when 1, 2-
diphenyldisulfane was added to the our system instead of 2a
,
only trace amount of 3aa was detected by GC-MS (eq 3). This
result demonstrated that the next step which followed CF3
radical attack should be a carboanion involved reaction. The
Scheme
4.
The
Synthetic
Utility
of
This
quantum yield for the reaction of 1a, 2a and CF3SO2Na under
Thiotrifluorometylation Reaction.
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Shen and C. Li, Org. Lett., 2017, 19, 698; (o) L. Wu, F. Wang, X.
make this transformation valuable and practical in organic
synthesis.
View Article Online
Wan, D. Wang, P. Chen and G. Liu, J. DAOmI:.1C0.h1e03m9./CS7oCcC.,023502107A,
139, 2904.
Financial support from the Recruitment Program of Global
Experts (1000 Talents Plan), the Natural Science Foundation of
Fujian Province (2016J01064), Fujian Hundred Talents Plan,
Program of Innovative Research Team of Huaqiao University
(Z14X0047), the Graduate Innovation Fund of Huaqiao
University (to W. K.). We also thank Instrumental Analysis
Center of Huaqiao University for analysis support.
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