Deaminative metal-free reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts

Article abstract of DOI:10.1039/d0cc07632e

A convenient and efficient approach to (E)-alkylsulfonyl olefinsviaa metal/light-free three-component reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts is described. This alkylsulfonylation proceeds smoothly with a broad substrate scope, leading to diverse (E)-alkylsulfonyl olefins in moderate to good yields. During the process, excellent functional group tolerance is observed and sodium metabisulfite is used as the source of sulfur dioxide. Mechanistic studies show that the alkyl radical generatedin situfrom Katritzky saltviaa single electron transfer with alkenylboronic acid or DIPEA is the key step for providing an alkyl radical intermediate, which undergoes further alkylsulfonylation with sulfur dioxide.

Full text of DOI:10.1039/d0cc07632e

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Deaminative metal-free reaction of alkenylboronic acids, sodium
metabisulfite and Katritzky salts
a
a
a
a,b,c
Tonghao Zhu, Jia Shen, Yuyuan Sun and Jie Wu*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
A convenient and efficient approach to (E)-alkylsulfonyl olefins via styrenes in the presence of carbon monoxide was disclosed by
5d
a metal/light-free three-component reaction of alkenylboronic Wu and co-workers. The above results showed that this metal-
acids, sodium metabisulfite and Katritzky salts is described. This free deaminative reaction of Katritzky salts was promising, since
alkylsulfonylation proceeds smoothly with a broad substrate scope, it would provide innovative routes for the construction of
leading to diverse (E)-alkylsulfonyl olefins in moderate to good complex functional molecules under mild conditions.
yields. During the process, excellent functional group tolerance is
observed and sodium metabisulfite is used as the source of sulfur
dioxide. Mechanistic studies show that alkyl radical generated in
situ from Katritzky salt via a single electron transfer with
alkenylboronic acid or DIPEA is the key step providing alkyl radical
intermediate, which undergoes further alkylsulfonylation with
sulfur dioxide.
Since amines are one of the most ubiquitous molecules in
natural products and pharmaceuticals, conversion of amino-
group for the synthesis of new functional molecules via the
Scheme 1. Synthesis of (E)-alkylsulfonyl olefins via the deaminative
insertion of sulfur dioxide.
In the past decade, sulfonylation from sulfur dioxide for the
construction of sulfonyl compounds has developed rapidly by
3
cleavage of C(sp )-N bond has been of great significance and has
1
attracted growing interest in synthetic community. Recently,
rapid progress has been witnessed for the chemistry of Katritzky
3
2
salts from alkylamines through the activation of C(sp )-N bond.
2 2
using DABCO·(SO ) and sodium/potassium metabisulfite as the
So far, Katritzky salts have been utilized broadly as alkyl radical
precursors in organic transformations. Usually, alkyl radicals are
generated under transition metal catalysis or visible-light
induced conditions via a single electron transfer process.3,4 In
6
sulfur dioxide surrogates. As part of our interests in sulfones,
we focused on the exploration in the method development for
the synthesis of vinyl sulfones through the insertion of sulfur
7
8
dioxide , due to their versatile reactivities in organic synthesis
2
018, Shi and co-workers described a metal-free deaminative
9
and importance in pharmaceuticals. For instance, vinyl sulfones
have been reported as a novel class of neuroprotective agents
toward Parkinson’s disease therapy. Prompted by the recent
borylation of Katritzky salts in absence of visible-light
5a
irradiation. Subsequently, Loh and co-workers reported the
synthesis of trans-1,2-disubstituted olefins under catalyst-free
conditions through a deaminative alkenylation of Katritzky salts
10
advance in the metal-free deaminative transformations of
Katritzky salts, we envisioned that vinyl alkylsulfones would be
produced from Katritzky salts with the insertion of sulfur
dioxide. Our previous result showed that in the presence of
visible light irradiation, photocatalytic deaminative insertion of
sulfur dioxide using Katritzky salts as alkyl radical precursors
5b
with alkenyl boronic acids. N-Heterocyclic carbene-catalyzed
deaminative carbonylation of Katritzky salts with aldehydes was
5c
demonstrated as well by Hong’s group. Later, a transition-
metal-free deaminative carbonylation of Katritzky salts with
1
1
would give rise to -keto sulfones (Scheme 1a). Encouraged
by this achievement and the result from Katritzky salts and
boronic acids, we hypothesized that the generation of (E)-
alkylsulfonyl olefins might be accessed under metal- and light-
free conditions (Scheme 1b). Herein, we described a convenient
a.School of Pharmaceutical and Materials Engineering & Institute for Advanced
Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China. E-mail:
jie_wu@fudan.edu.cn.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic
Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032,
b.
China.
and efficient approach to (E)-alkylsulfonyl olefins via
metal/light-free three-component reaction of alkenylboronic
acids, sodium metabisulfite and Katritzky salts. This
a
c.
School of Chemistry and Chemical Engineering, Henan Normal University
Electronic Supplementary Information (ESI) available: Experimental details and
spectral data, copies of H, C and F NMR spectra. See DOI: 10.1039/x0xx00000x
†
1
13
19
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Journal Name
o
alkylsulfonylation proceeds smoothly with a broad substrate 80 C (Table 1, entries 8 and 9). Additionally, after optimization
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scope, leading to diverse (E)-alkylsulfonyl olefins in moderate to of the substrate ratio, the correspondDinOgI: 1p0r.1o0d3u9/cDt0C3aCa076w32aEs
good yields. During the process, excellent functional group afforded in 77% isolated yield (Table 1, entry 12).
tolerance is observed and sodium metabisulfite is used as the
source of sulfur dioxide. Mechanistic studies show that alkyl Table 2. Scope exploration for the metal/light-free three-component
radical generated in situ from Katritzky salt via a single electron reaction of alkenylboronic acids
transfer with alkenylboronic acid or DIPEA is the key step metabisulfite a,b
providing alkyl radical intermediate, which undergoes further
alkylsulfonylation with sulfur dioxide.
1, Katritzky salts 2 and sodium
Table 1. Effects of variation of reaction parameters a
Entry
1
Variation of conditions
none
Yield (%)b
32
2
other bases instead of DIPEA
NMP instead of DMF
other solvents instead of DMF
trace to 24
3
38
trace to 27
65
4
5c
6c
7c
8c
9c
0c,d
1c,d
2c,d
Na
instead of DABCO·(SO
2
S
2
O
5
2
)
2
K
2
S
2
O
5
instead of DABCO·(SO
2
)
2
49
3.0 equiv. of DIPEA
1.5 equiv. of DIPEA
1.0 equiv. of DIPEA
50 oC
59
71
39
1
1
1
trace
36
110 oC
1.2 equiv. of 2a
77(72)
a
Reaction condition: alkenylboronic acid 1a (0.2 mmol, 1.0 equiv),
DABCO·(SO (0.3 mmol, 1.5 equiv), 1-cyclohexyl-2,4,6-triphenyl-
)
2 2
pyridin-1-ium tetrafluoroborate 2a (0.3 mmol, 1.5 equiv), DIPEA (0.4
mmol, 2.0 equiv), DMF (1.0 mL), N
2
, 80 C, 12 h. b 1H NMR yield using
o
a
Reaction condition: alkenylboronic acid
1 (0.3 mmol, 1.0 equiv),
1
,3,5-trimethoxybenzene as internal standard (Isolated yield in
parentheses). c NMP was employed as the solvent. In the presence of
d
sodium metabisulfite (0.45 mmol, 1.5 equiv), Katritzky salt
2
(0.36 mmol,
o
1
b
.2 equiv), DIPEA (0.45 mmol, 1.5 equiv), NMP (1.5 mL), N
2
, 80 C, 12 h.
DIPEA (0.3 mmol, 1.5 equiv)
.
Isolated yield based on alkenylboronic acid 1.
Initial investigation was carried out for the reaction of (E)-
Having identified effective conditions, we next evaluated the
synthesis of (E)-alkylsulfonyl olefins via a metal/light-free three-
component reaction of alkenylboronic acids sodium
metabisulfite and Katritzky salts . The results are summarized
in Table 2. At the outset, we explored the substrate scope of
alkenylboronic acids . Generally, various alkenylboronic acids
bearing either electron-withdrawing or electron-donating
styrylboronic acid 1a, DABCO·(SO
2
)
2
and 1-cyclohexyl-2,4,6-
o
triphenyl-pyridin-1-ium tetrafluoroborate 2a in DMF at 80 C
using N,N-diisopropylethylamine (DIPEA) as a base. To our
delight, the desired product 3aa was produced in 32% yield
1
,
2
(Table 1, entry 1). Further exploration of other bases revealed
1
that DIPEA was the best choice (Table 1, entry 2, for details see
ESI). Evaluation of solvents showed that product 3aa could be
generated in 38% yield by using 1-methyl-2-pyrrolidinone (NMP)
instead of N,N-dimethylformamide (DMF) as the solvent (Table
1
groups were applicable in this transformation, giving rise to the
corresponding (E)-alkylsulfonyl olefins 3aa-3la in 37-85% yields.
A variety of functional groups including halo (F, Cl, Br), CF
3
, CN,
1
, entry 3). However, the results were inferior when other
CO Me, OMe and OAc were all compatible under the standard
2
solvents were used as a replacement of DMF (Table 1, entry 4,
for details see ESI). Fortunately, the yield of compound 3aa was
dramatically improved when sodium metabisulfite was
employed as the sulfur dioxide surrogate, and the result from
potassium metabisulfite was not better (Table 1, entry 5 vs
entry 6). Further optimization revealed that increasing the
amount of DIPEA could not improve the final outcome (Table 1,
entry 7). Interestingly, a higher yield was obtained when the
amount of DIPEA was decreased to 1.5 equiv (71%, Table 1,
entry 8). Subsequently, the effect of reaction temperature was
evaluated. It was found that the reaction worked efficiently at
conditions. Additionally, reaction of (2-(naphthalen-2-
yl)vinyl)boronic acid 1m worked efficiently, leading to the target
product 3ma in 76% yield. The substrate with thiophene
substituent was suitable as well, providing the expected
product 3na in 42% yield. Subsequently, the scope of Katrizky
salts
2 prepared from alkyl amines was evaluated. The results
showed that both cyclic and chain alkyl amine derivatives were
workable in the transformation, giving rise to the desired
products in moderate to good yields. Unfortunately, alkyl-
substituted alkenylboronic acids 1o and 1p were not suitable in
2
| J. Name., 2012, 00, 1-3
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Journal Name
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this transformation. Moreover, the reaction failed to provide could be trapped by TEMPO (Scheme 3, eqn d). HVioewwAertvicelerO, ntlhinee
the desired product when Katritzky salt 2n or 2o from amino cyclohexyl radical was not detectedDOwI:h1e0n.103s9t/yDr0eCnCe076w32aEs
acids was employed in the reaction of (E)-styrylboronic acid 1a employed in the presence of DIPEA (Scheme 3, eqn e), which
and sodium metabisulfite.
indicated that the formation of alkyl radical might go through a
single electron transfer (SET) between alkenylboronic acid and
Katrizky salt.
Scheme 2. Synthesis of (E)-alkylsulfonyl olefins via the decarboxylative
insertion of sulfur dioxide.
Moreover, further exploration revealed that not only
Katrizky salts but also N-hydroxyphthalimide (NHP) esters12
could be applied as the alkyl radical precursors in the synthesis
of (E)-alkylsulfonyl olefins via a deaminative insertion of sulfur
dioxide. Several examples are presented in Scheme 2.
Scheme 4. Proposed mechanism.
Prompted by the above results and related reports,5 we
proposed a plausible mechanism as shown in Scheme
reasoned that assisted by organoboronic acid under thermal
conditions, alkyl radical would be formed from Katrizky salt
4. We
2
via a single electron transfer process. This alkyl radical would be
trapped by sulfur dioxide from sodium metabisulfite,13 giving
rise to alkylsulfonyl radical. Subsequently, addition of
alkylsulfonyl radical to alkenylboronic acid
generating a more stable radical intermediate
process between radical intermediate
would take place, leading to alkyl radical and cation
intermediate II In the presence of base, this cation
intermediate II would undergo deboronization to provide the
desired product
In conclusion, we have developed
1
would occur,
I. Another SET
I
and Katrizky salt 2
.
3
.
a
convenient and efficient
approach to (E)-alkylsulfonyl olefins via a metal/light-free three-
component reaction of alkenylboronic acids, sodium
metabisulfite and Katritzky salts. This alkylsulfonylation
proceeds smoothly with a broad substrate scope, leading to
diverse (E)-alkylsulfonyl olefins in moderate to good yields.
During the process, excellent functional group tolerance is
observed and sodium metabisulfite is used as the source of
sulfur dioxide. Mechanistic studies show that alkyl radical
generated in situ from Katritzky salt via a single electron transfer
with alkenylboronic acid or DIPEA is the key step providing alkyl
Scheme 3. Control experiments.
Additionally, to gain more insights for the reaction pathway,
several control experiments were performed. It was found that
only a trace amount of product 3aa was detected when 4,4,5,5-
tetramethyl-2-styryl-1,3,2-dioxaborolane 1a’ was used instead
of styrylboronic acid 1a (Scheme 3, eqn a). No reaction occurred
when styrene was employed as a replacement under the
standard conditions (Scheme 3, eqn b). These results
demonstrated the crucial role of organoboronic acids in the
transformation. Moreover, the model reaction was completely
hampered in the presence of 2,2,6,6-tetramethyl-1-
piperidinyloxy (TEMPO) or 2,6-di-tert-butyl-4-methylphenol
radical
intermediate,
which
undergoes
further
alkylsulfonylation with sulfur dioxide.
Financial support from National Natural Science Foundation of
China (Nos. 21871053 and 21532001), the Leading Innovative
and Entrepreneur Team Introduction Program of Zhejiang (No.
2
019R01005), and the Open Research Fund of School of
Chemistry and Chemical Engineering, Henan Normal University
2020ZD04) is gratefully acknowledged.
(
(BHT) (Scheme 3, eqn c). These results revealed that this
conversion might undergo a radical process. In order to verify
the formation of alkyl radical, the model reaction was carried
out in the absence of DIPEA. It was found that cyclohexyl radical
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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