Organo-selenium mediated regio- and stereoselective iodoselenylation of alkynes in an aqueous medium: Simple access to (: E)-β-iodoalkenyl selenides

Article abstract of DOI:10.1039/c9ob00524b

A method for the simple and efficient iodoselenylation of simple alkynes under mild conditions using commercially available molecular iodine (I₂) and diorganoyldiselenides as starting materials has been developed. A broad range of alkynes can b

Full text of DOI:10.1039/c9ob00524b

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Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
benzene
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DOI: 10.1039/C9OB00524B
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Organo-Selenium Mediated Regio- and Stereoselective
Iodoselenylation of Alkynes in an Aqueous Medium: Simple Access
to (E)-β-Iodoalkenyl Selenides
Received 00th January 20xx,
Accepted 00th January 20xx
Xianghua Zeng a*, Lu Chen b*
DOI: 10.1039/x0xx00000x
www.rsc.org/
A method for the simple and efficient iodoselenylation of (Scheme 1a) 9. In 2010, the Nishiyama group prepared β-bromo
simple alkynes under mild conditions using commercially alkenyl phenyl selenides via a CuI-bpy-catalyzed reaction
available molecular iodine (I2) and diorganoyldiselenides as between various alkynes and diphenyl diselenide under air
starting materials has been developed. A broad range of (Scheme 1b) 10. In 2016, Zeni and co-workers employed
alkynes can be employed to afford (E)-β-iodoalkenyl selenides biphenyl-2-alkyne derivatives as common starting materials for
in good to excellent yields and with high regio- and the preparation of both 9-iodo-10-organochalcogen-
stereoselectivity without the need for any protecting groups.
phenanthrenes and 9-organochalcogen-phenanthrenes via
electrophilic cyclization and iron(III) chloride and diorganyl
Hetero-atom functionalized aromatic and heteroaromatic diselenide-mediated intramolecular cyclization, respectively
structural motifs are present in numerous natural products and (Scheme 1c) 11
medicines, thus the synthesis of structures containing these
.
Scheme 1 Synthetic strategy for the formation of β-haloalkenyl
skeletons is of high importance 1. A number of synthetic
strategies have been developed to synthesize hetero-atom
functionalized compounds. For example, compounds bearing
alkenyl heteroatoms can be prepared via the simultaneous
selenides
Previous Work
I
Se
R
I2 (1.1 eq)
2
introduction of two heteroatom groups into an alkyne bond .
Se
R
(a)
R'
R'
CH2Cl2, RT, 1-3 h
O
Organoselenium compounds exhibit anti-oxidant activities, and
may play a role in certain diseases such as cancer, heart diseases,
inflammatory processes and arthritis, etc 3. Although significant
progress has been made towards the halogen-functionalization
of alkynes, the halogen-selenylation of alkynes has not been
OMe
R=aryl, alkyl
R
Br
CuI-bpy (5 mol%)
TBAB (1.05 eq)
R
(b)
Se
Ph-Se-Se-Ph
AcOH, 100 oC, air, 18h
R=Me, CH2OH
4
I
widely reported . Substituted β-haloalkenyl selenides are of
I2 (3 eq)
Se
R
Se
K2CO3 (0.5 eq)
particular importance because they are not only found in the
structures of bioactive and drug molecules, but are also
important building blocks in organic synthesis. In this context,
numerous synthetic methods towards the preparation of
halofunctionalized vinyl selenides have been developed 5-8. In
2009, Zeni and co-authors reported the use of 2-
chalcogenealkynylanisoles for the preparation of 3-iodo-2-
chalcogen-benzo[b]furans in CH2Cl2 at room temperature
R
(c)
(d)
THF, RT, air, 3-12 h
Ar
R=aryl, alkyl
This Work: one-pot reaction
I
R2
I
2 (1.1 eq)
R2
Se
3
3
+
Se Se
-R
R -
-
R1
R1
EtOH/H2O, 70 oC, air, 30 min
R3
R1=aryl, alkyl; R2= aryl, alkyl, H
R3=aryl, alkyl
E/Z=80:20 to 99:1
Yield: 85% to 96%
Based on our previous reports 12 and as part of our efforts
aimed at developing new synthetic methodologies for the
a College of Biological, Chemical Science and Engineering, Jiaxing University,
118 Jiahang Road, Jiaxing 314001, China; E-mail:
xianghuazeng@mail.zjxu.edu.cn
preparation of heterocycles and heteroatom-containing
13
b School of Biotechnology and Health Science, Wuyi University, Jiangmen,
Guangdong Province 529090, China, E-mail: wyuchemcl@126.com;
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
compounds
. We herein divulge a highly regio- and
stereoselective synthesis of (E)-β-iodoalkenyl selenides via the
reaction of various alkynes with molecular iodine and
diorganoyldiselenides
under
mild
conditions
using
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environmentally friendly aqueous media. Initially, we focused
on developing a more efficient protocol in vitue of the reaction
of 1a and 2a as a model system. After the screening reaction, an
optimal yield (95%) and the ratio of E:Z to 97:3 of 3a was
obtained (See Table S1 in Supporting Information I (SI)). Under
the optimized reaction conditions (Table S1, entry 10), we
examined the scope and limitations of the iodoselenylation, the
results for which are shown in Table 1. More specifically, 1-
ethynyl-4-methylbenzene and 1-ethynyl-3-methylbenzene
underwent iodoselenation successfully to afford the
corresponding β-iodoalkenyl selenides in 94-96% yields and
with excellent stereoselectivities (Table 1, 3b and 3c). We next
a
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DOI: 10.1039/C9OB00524B
Reaction conditions: Unless otherwise stated, alkynes (0.50
mmol), diselane (0.25 mmol), I2 (0.275 mmol) in EtOH/H2O (2:1,
1.5 mL) at 70 oC for 30 min under air atmosphere. b isolated yield.
Additionally, we also investigated the influence of electron-
deficient substituents, including –Cl and –F groups, at the para-
position of the aryl ring. The desired products were obtained in
satisfactory yields (Table 1, 3i and 3j). The results show that the
electronic character of the aryl ring does not have a significant
influence on this transformation. The use of N-(4-
ethynylphenyl)-4-methylbenzenesulfonamide as a substrate
gave product 3k in 87% yield; the stereochemistry and precise
configuration
unambiguously confirmed by single-crystal X-ray analysis.
Interestingly, heteroaryl acetylenes, including 2-
of
(E)-β-Iodoalkenyl
selenide
were
employed
ethynylbenzene,
the
electron-rich
1-ethynyl-4-propylbenzene,
compounds
1-ethyl-4-
1-butyl-4-
ethynylbenzene, 1-ethynyl-4-heptylbenzene and 1-ethynyl-4-
methoxybenzene as substrates, and the corresponding
products were obtained with excellent regioselectivity and
stereoselectivity (Table 1, 3d-3h).
ethynylthiophene and 3-ethynylthiophene, also served as
effective coupling partners and generated their corresponding
β-iodoalkenyl selenides in high yields (Table 1, 3l and 3m).
To further expand the substrate scope, we turned our
attention to the application of terminal alkyl acetylenes. As
illustrated in Table 1, substrates bearing alkyl chains, such as n-
oct and n-butyl compounds, underwent efficient coupling to
produce the desired products in 85-87% yield (Table 1, 3n and
3o). We then tested the reactivity of different diselanes with
Table 1 Substrate scope of terminal alkynes a,b
I2
I
Se
R'
+
R'
Se
R
EtOH/H2O, 70 oC, 0.5 h
R'
e
R
S
this
protocol.
1,2-Bis(4-chlorophenyl)diselane,
1,2-dihexyldiselane and
1,2-
1,2-di-p-
I
I
I
dimethyldiselane,
tolyldiselane were all well tolerated, affording the
corresponding products in 90-96% yield (Table 1, 3p-3t).
Se
Se
Se
Me
Me
3b
3a
: E/Z=97:3
: E/Z=98:2
96% yield
3c
: E/Z=90:10
94% yield
Table 2 Substrate scope of internal alkynes a,b
95% yield
I
I
R2
I2
I
R3
Se
R3
R1
R2
Se
+
Se
Se
R3
EtOH/H2O, 70 oC, 0.5 h
R1
e
S
1
3
2
TsHN
X
3d
X = Et, : E/Z=99:1, 91% yield
3e
X = n-Pr, : E/Z=96:4, 95% yield
I
3f
X = n-Bu, : E/Z=96:4, 96% yield
I
I
3g
X = n-Hep, : E/Z=89:11, 96% yield
Se
3h
X = OMe, : E/Z=80:20, 90% yield
Se
Se
3i
X = Cl, : E/Z=85:15, 95% yield
CCDC:1882045
: E/Z=99:1, 87% yield
3j
X = F, : E/Z=99:1, 96% yield
3k
3v
: E/Z=90:10
94% yield
3w
I
: E/Z=95:5
90% yield
3u
: E/Z=93:7
92% yield
I
I
I
Se
Se
Se
n=4
I
I
S
S
3m
Se
Se
Se
Me
3n
I
: E/Z=85:15
85% yield
3l
: E/Z=86:14
94% yield
: E/Z=85:15
90% yield
n=5
n=5
3x
: E/Z=93:7
90% yield
3y
: E/Z=94:6
95% yield
3z
: E/Z=95:5
95% yield
I
I
Se
Cl
Se
Cl
Se
n=2
3o
a
Reaction conditions: Unless otherwise stated, alkynes (0.50
mmol), diselane (0.25 mmol), I2 (0.275 mmol) in EtOH/H2O (2:1,
1.5 mL) at 70 oC for 30 min under air atmosphere. b isolated yield.
3q
: E/Z=95:5
96% yield
Cl
: E/Z=85:15
87% yield
3p
I
: E/Z=89:11
91% yield
I
I
In addition to terminal alkynes, we also employed internal
alkynes as substrates, including diaryl, arylalkyl and dialkyl
compounds. Reaction with these substrates proceeded
smoothly, affording the desired products in good yields (Table
2, 3u-3w). In comparison with previously reported protocols,
this represents the first example of the preparation of
difunctionalized alkenes with internal alkynes. Furthermore, we
Se
Se
Se
n=5
3r
: E/Z=99:1
86% yield
3s
: E/Z=80:20
90% yield
3t
: E/Z=95:5
94% yield
2 | J. Name., 2012, 00, 1-3
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employed 1,2-di-p-tolyldiselane and 1,2-diheptyldiselane as
substrates for reaction with oct-4-yne and 1,2-diphenylethyne,
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In order to gain mechanistic insight intDoOtIh: 1e0r.1e0a3c9t/iCo9nO,Bs0e0v5e2r4aBl
and the target products were obtained in high yields (Table 2, control experiments were performed. First, we performed the
3x-3z).
reaction of phenyl(phenylethynyl)selane and I2 under the
optimal conditions and the unexpected disubstituted
iodoalkenyl selenide 7a was obtained (Scheme 4A). When (E)-
(1,2-diiodovinyl)benzene was employed as a substrate under
the standard conditions, the desired product 4a was obtained
(Scheme 4B). Next, we selected phenylacetylene and phenyl
hypoiodoselenoite as starting materials for reaction under the
standard conditions and the target product 4a was obtained in
good yield and stereoselectivity (Scheme 4, C).
Scheme 2 Synthesis of β-haloalkenyl selenides
Br
NBS (0.22 mmol)
standard condition
Se
Se
Se
(a)
+
+
+
4a
: E/Z=71:29
95% yield
0.1mmol
0.2 mmol
Cl
NCS (0.22 mmol)
standard condition
Se
Se
Se
(b)
(c)
4b
: E/Z=58:42
94% yield
Scheme 4 Control experiments
0.1mmol
0.2 mmol
0.2 mmol
F
I
I
Se
Se
Selectfluor(0.22 mmol)
standard condition
Se
I2 (1.1 eq)
Se
(A)
Se
0.2 mmol
standard condition
0.1mmol
4c:
7a
: 78% yield
no reaction
I
I
Se
To explore the generality of this protocol, we selected NBS
and NCS as halogen sources to promote this transformation
under the standard conditions. The expected bromoalkenyl and
chloroalkenyl selenides were obtained, respectively, but with
relatively poor E:Z selectivity (Scheme 2a and Scheme 2b).
When we employed selectfluor as a halogen source in this
model reaction, the expected product 4c was not detected
(Scheme 2c).
I
standard condition
Se
Se
no reaction
(B)
(C)
+
0.1 mmol
Se
0.2 mmol
I
standard condition
I
Se
+
0.2 mmol
0.2 mmol
3a
: E/Z=98:2, 95% yield
I
I2 (0.22 mmol)
TEMPO (2 eq)
Se
Se
Se
+
(D)
(E)
standard condition
Scheme 3 Synthetic applications
0.2 mmol
0.1 mmol
3a
: E/Z=97:3, 95% yield
Br
I
I2 (0.22 mmol)
BHT (2 eq)
Se
, 89% yield
Se
Se
Se
7a
Se
E-4a, E/Z=88:12, 81% yield
Condition D
+
standard condition
Condition C
SH
0.2 mmol
99%
0.1 mmol
3a
: E/Z=97:3, 91% yield
I
I
S
Se
Cl
Se
R
O
Condition A
Me
94%
O
I
D
Condition B
Me
Se
D
(F)
E-3: R=H, Cl
I2 (0.11 mmol)
R
Cl
Se
E-5a, 78% yield
Se
Se
+
Condition E
NC
standard condition
Condition F
E-6a, 56% yield
0.2 mmol
0.1 mmol
3a-D
: E/Z=97:3, 92% yield
Se
Se
It was found that the addition of a radical scavenger (2 equiv
E-8a, 52% yield
E-9a, 92% yield
of TEMPO or BHT) had no effect on the reaction outcome,
suggesting that a single electron transfer process might not be
involved in this iodoalkenyl selenide reaction (Scheme 4D, and
4E). Furthermore, by replacing phenylacetylene with
deuterated phenylacetylene and carrying out the reaction
under the optimal conditions with PhSeSePh and I2, the
corresponding β-iodoalkenyl selenide was obtained in 92% yield
as a mixture of deuterated products with a ratio of 94:6
deuterated 3a-D/non-deuterated 3a-H. These results provide
evidence that the reaction proceeds with hydrogen retention
on the phenylacetylene starting material (Scheme 4F).
Reaction conditions: (A) 3q (0.2 mmol), mCBPA (3 eq), CH2Cl2 (2mL), 40
oC, 12h, under N2. (B) 3a (0.2 mmol), p-toluenethiol (1.1 eq), CuI (0.1eq),
o
Et3N (2eq), 1,4-dioxane (2mL), 25 C, 8h, under N2. (C) 3a (0.2 mmol),
Cs2CO3 (2eq), H2O (2mL), 100 oC, 12h, under N2. (D) 3a (0.2 mmol), CuBr2
o
(2eq), THF (2mL), 40 C, 24h, under N2. (E) 3a (0.2 mmol), Cu2O (1eq),
phenylacetonitrile (1.5eq), DMF (2mL), 130 oC, 12h, under air. (F) 3a (0.2
mmol), phenylboronic acid (1.5 eq), Pd(PPh3)4 (0.1eq), K2CO3 (2eq),
DMF/H2O (2 mL/0.2 mL), 100 oC, 12h, under N2.
The synthetic utility of the β-Iodoalkenyl selenide products
was also explored. Selenide 3q could be oxidized with mCPBA in
dichloromethane solvent to give the corresponding compound
E-5a in 78% yield. Furthermore, selenide 3a was treated under
standard Ullmann-type coupling14, dehydroiodization,
bromination15, cyanation16 and Suzuki17 conditions, providing
the corresponding coupling products 4a and 6a-9a in good
yields (Scheme 3).
On the basis of the above findings, a plausible reaction
pathway is depicted in Scheme 5. Initially, the presence of I2
leads to electrophilic addition to the 1,2-diphenyldiselane to
form phenyl hypoiodoselenoite A, which subsequently reacts
6
with phenylacetylene to form intermediate B or C . I- then
undergoes nucleophilic attack at the more substituted site of B
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leading to ring opening via the possible intermediate C,
affording difunctionalized product 3.
Scheme 5 Proposed reaction mechanism
R1
Se+
4
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1
H
I
H
R2
H
Se
I-
R1
I2
R1
Se
R1
I
Se R1
R2
R2
R1
Se
R2
H
Se
2
3
B
A
C
Conclusions
In summary, we have developed a new environmentally
friendly, economical and straightforward approach to the
synthesis of β-haloalkenyl selenides from readily available and
inexpensive diselanes and I2 with various aryl and alkyl alkynes.
In comparison with previously reported protocols, the
developed chemistry is also amenable to the transformation of
internal alkynes, including halo-substituted compounds. The
transformation proceeds in aqueous ethanol under mild
conditions, furnishing the desired products in good to excellent
isolated yields. The protocol is adaptable to a broad substrate
scope with good functional group tolerance and provides an
important foundation for the efficient preparation of functional
alkenes from non-activated alkynes.
5
6
7
8
Acknowledgements
9
F. Manarin, J. A. Roehrs, R. M. Gay, R. Brandao, P. H. Menezes,
C. W. Nogueira and G. Zeni. J. Org. Chem., 2009, 74, 2153–
2162.
The authors are grateful to the funds of the Natural Science
Foundation of Zhejiang Province (LY17B030011), Science
Foundation for Young Teachers of Wuyi University (2016zk03),
the Foundation of the Department of Education
10 a) N. Taniguchi. Synlett., 2008, 6, 849–852; b) N. Taniguchi.
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Guangdong Province
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2017KZDXM085,
12 X. Zeng, L. Chen. Org. Biomol. Chem., 2018, 16, 7557-7560.
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professor Pierre H. Dixneuf for helpful discussion during
manuscript preparation.
14 P. E. Fanta, Synthesis, 1974, 9–21.
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