Cu(ii)-catalyzed sulfide construction: both aryl groups utilization of intermolecular and intramolecular diaryliodonium salt

Article abstract of DOI:10.1039/c6cc09201b

A sulfur-iodine exchange protocol of diaryliodonium salts with inorganic sulfur salt was developed. Both aryl groups in the diaryliodonium salt were fully exerted in this transformation. Five- to eight-membered sulfur-containing heterocycles were achieved. Note that [1]benzothieno-[3,2-b][1]benzothiophene (BTBT) (an organic field-effect transistor (OFET) material) and Zaltoprofen were efficiently established through this method.

Full text of DOI:10.1039/c6cc09201b

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Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
Reactivity differences of Sc3N@C2n (2n 68 and 80). Synthesis of the
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Cu(II)-Catalyzed Sulfide Construction: Both Aryl Groups Utilization
of Intermolecular and Intramolecular Diaryliodonium Salt
Ming Wang,a Jianpeng Wei,a Qiaoling Fana and Xuefeng Jiang*ab
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
(A) Significant Functional Sulfides
A sulfur-iodine exchange protocol of diaryliodonium salts with
inorganic sulfur salt was developed. Both aryl groups in
diaryliodonium salt were fully exerted in this transformation. Five-
to eight-membered sulfur-containing heterocycles were achieved.
Notably, key unit of [1]benzothieno-[3,2-b][1]benzothiophene
(BTBT) as organic field-effect transistor (OFET) material and
Zaltoprofen were efficiently established through this method.
♦ Semiconductor material
♦ Pharmaceutical
S
S
S
Me
COOH
S
S
O
DNTT
BTBT
Zaltoprofen
(B) Both Aryl Groups Utilization of Diaryliodonium Salt
(1) Greaney's work: C-C, C-N Bonds Formations
Ar1
Sulfur-containing molecules extensively exist in materials,1
natural products,2 pharmaceuticals,3 and even food.4 In
organic photoelectric materials, sulfur atom plays the unique
role owing to its higher resonance energy than other
heteroatoms.1c For example, thienothiophenes, thienoacenes
and their derivatives are well-known organic functional
material structure for thin film transistors.1 More than 20% of
top 200 U.S. prescriptions drugs were sulfur-containing drugs,
and the percentage is still fleetly increasing.3a Thiophene,
thiazepine and thiazine structures are typically occured in
several famous pharmaceuticals (Scheme 1, A).3 Traditionally,
these widely existent heterocyclic sulfide structures were
X'
Cu(I)
I
R
Ar1
Ar2
R
+
C-arylation
N-arylation
N
N
H
Ar2
(ref.14: JACS, 2015, 137, 1416)
(2) Our Approach: I-S Exchange in One Step
I
S
I-S Exchange
X'
S source
S
I
Ar1
Ar2
2.66
Ar1
Ar2
Electronegativity
2.58
1.04
one step
Atomic Radius (Å) 1.33
Two C-S Bonds Formations
(3) This work:
X
√
√
Intermolecular
S
I
Sulfur salt
(symmetrical & unsymmetrical)
Ar1
Ar2
Ar1
Ar2
Cu(II)/L
Intramolecular
up to 91% yield
(5- to 8-membered ring)
♦ Both Aryl Groups Employment
♦ Odourless Inorganic Sulfur Salt
♦ The Late Stage Introduction Sulfur
♦ Material and Pharmaceutical Syntheses
synthesized through cross-coupling between thiophenols and
aryl halides followed by cyclization.1c,
Scheme 1 Functional sulfides and diaryliodonium salts chemistry.
5
Nevertheless,
stable and abundant inorganic sulfur source for sulfur
introduction in the late stage is highly desirable.
Diaryliodonium salt is an air-/moisture-stable and well-
established reagent reported by Hartmann and Meyer since
1894,6 which is prepared easily by one step process7 and has
shown to be one of the most efficient arylation reagent in
organic synthesis.8 Cross-coupling reactions involving
diaryliodonium salts with arenes,9 alkynes,10 alkenes,11
heteroatoms12 and carbonyl compounds13 have been well
developed, in which diaryliodonium salt was generally applied
as a single arylation reagent. The applications of both aryl
groups in diaryliodonium salt were concerned recently.
Greaney group reported the first intermolecular
diaryliodonium salts for double arylation of indole (Scheme 1,
B1).14 There is no other example describing the both aryl
groups transformation of intermolecular diaryliodonium salt.
Despite some elegant works of intramolecular diaryliodonium
salts were explored,15 it will be challenge to avoid the homo-
introduction of sulfur in the early stage of synthetic process
confronts with several conundrums: 1) Poison effect toward
catalysts in the following steps due to strong coordination
from sulfur to transition metals. 2) Over-oxidization to
disulfide, sulfoxides, and sulphones due to sensitivity to
oxidative conditions. 3) Environmental-unfriendly poison and
smelly thiophenol application. Since extensive application of
sulfides mentioned above, the methodology of using odourless,
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coupling product in the both utilization of intermolecular diaryliodonium salts derived from aryl iodides with various
diaryliodonium salt. Continuous with our concept of sulfur substituents (2a 2h). The unsymmetrical diaryl sulfides 2i
-
atom transfer study,16 it was envisioned that sulfur-iodine could be obtained as well when 4-phenoxyl was installed
exchange for sulfide construction can stem from their similar instead of 4-methoxyl. Notably, phenyl-pyridine and phenyl-
electronegativity and atomic radius property by electron uracil iodonium salts were good candidates for corresponding
equilibration between sulfur and iodine(III) (Scheme 1, B2). aryl sulfides 2j-2k construction.18 Logically, symmetrical
Herein, we reported a new strategy for highly efficient diphenyl-sulfide (2l) was readily achieved through exchanging
construction of sulfides through double arylation of sulfur between diphenyliodonium salt and potassium thioacetate.
atom. This strategy, taking potassium thioacetate as sulfur Both electron-withdrawing (2m) and –neutral substituent (2n
)
source in the late stage of functional sulfide synthesis, was on phenyl rings formed desired products smoothly. What
compliant with both intermolecular and intramolecular sulfur- needs to be pointed out, ortho-position substituted with
iodine exchange (Scheme 1, B3).
methyl did not impede the exchanging, affording sulfides 2o
and 2p in 69% and 44% yield respectively.
Table 1 Conditions optimizationa
Table 2 Intermolecular sulfur-iodine exchangea
Entry
1c
2c
3c
4c
5c
6c
7c
S Source
S8
Solvent
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
DMF
X
Yield (%)b
trace
trace
trace
15
BF4
BF4
BF4
BF4
BF4
BF4
BF4
BF4
BF4
BF4
BF4
OTf
OTs
I
Na2S2O3
(NH2)2C=S
Na2S
K2S
18
KSAc
KSAc
KSAc
KSAc
KSAc
KSAc
KSAc
KSAc
23
32
8
DMF
71
9
DMA
56
10
11
12
13
Dioxane
DMSO
DMSO
DMSO
DMSO
27
77
aThe reaction conditions:
1 (0.1 mmol), KSAc (0.2 mmol), Cu(OTf)2
72
(0.01 mmol), 1, 10-phenanthrolin (0.012 mmol), K3PO4 (0.2 mmol),
DMSO (1 mL). Isolated yields. bPerformed at 80 oC. cTriflate was instead
of tosyloxy. dTetrafluoroborate was instead of tosyloxy.
87
14
KSAc
69
a
b
Table 3 Intramolecular sulfur-iodine exchange a
The reactions were carried out with 0.1 mmol of 1a in 1 mL of solvent.
Isolated yields of 2a. c Performed at room temperature.
We
commenced
our
study
with
unsymmetric
diaryliodonium salt 1a and different inorganic sulfur sources
catalyzed by copper in methanol at room temperature.
Potassium thioacetate,17 possessing electron-withdrawing
acetyl on sulfur, was shown to be the best result and
generated desired unsymmetrical aryl sulfides 2a in 23% yield
(Table 1, entries 1-6). N, N-Dimethylformamide was chosen as
solvent instead of methanol to restrain the formation of
symmetrical aryl sulfides 2a′ as by-product (Table 1, entry 7),
in order to averting alcoholysis of acetyl. Higher temperature
helped to promote the transformation to 71% (Table 1, entry
8). Dimethyl sulfoxide was fixed to be the solvent giving better
yield of 2a in 77% (Table 1, entries 9-11). Counter anions in
diaryliodonium salts also played a crucial role for 2a formation.
87% of unsymmetric sulfide 2a was achieved when tosyloxy
served as anion (Table 1, entries 12-14).
aThe reaction conditions:
(0.01 mmol), 1, 10-phen (0.012 mmol), K3PO4 (0.2 mmol), DMSO (1 mL).
Isolated yields. bTriflate was instead of tosyloxy. c80 oC. d60 oC.
3 (0.1 mmol), KSAc (0.2 mmol), Cu(OTf)2
With optimized conditions in hand, intermolecular
construction of unsymmetrical diaryl sulfides were sysmatically
probed (Table 2). Different kinds of unsymmetrical diaryl
sulfides were efficiently achieved through corresponding
Following success of intermolecular sulfur-iodine exchange,
intramolecular diaryl sulfides were further studied for widely
existing sulfur-containing heterocycles in materials and
pharmaceuticals
(Table
3).
Five-membered
sulfur
2 | J. Name., 2012, 00, 1-3
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heteroaromatics with diverse electronic properties were was highly efficiently synthesized from diaryliodonium salt 3r
,
afforded in good to excellent yields (4a 4g), which is a core followed by only two steps of hydrolysis and oxidation
-
structure in OFET materials.1 Heteoaryl sulfides, derived from (Scheme 3b), which provided a new synthetic route for
corresponding iodonium salts, could be also accommodated Zaltoprofen, different from the traditional strategy.21
and furnished important multi-heterocyclic material structures
4h and 4i. Six-membered sulfur-containing heterocyclic, which
are of great importance in biological active lead compound
structures,19 were obtained in 62-84% yields
(4j-4m).
Remarkably, even seven- and eight-membered diaryliodonium
salts efficiently formed the corresponding seven- and eight-
membered sulfur-containing heterocyclic products (4n-4p) in
good yields, which were kernel structures of pharmaceutical
intermediate.5f These results indicated that sulfur-iodine
exchange processed predominant compatibility for different
size ring formation.
Scheme 3 Application in the syntheses of BTBT and Zaltoprofen.
In summary, an efficient sulfur-iodine exchange protocol
between odourless safe sulfur salt and readily available
diaryliodonium salts was developed. Both intermolecular and
intramolecular sulfur-iodine exchanging process performed
well to afford different types of functional sulfur-containing
structures, which introduce sulfur in the late stage as a
practical approach for the construction of sulfides. New
pathways of the semiconductor material BTBT and non-
steroidal anti-inflammatory drug Zaltoprofen exhibited great
potential of this method. Further explorations of
diaryliodonium salts are in progress in our laboratory.
Scheme 2 The plausible mechanism.
In order to figure out the mechanism of sulfur-iodine
exchange reaction, we tried to detect key intermediates
o
through decreasing the temperature to 25 C, which gave the
We are grateful for financial support provided by NSFC
(21672069, 21472050, 21272075), NSFC (21502054 for MW),
DFMEC (20130076110023), Fok Ying Tung Education
Foundation (141011), Program for Shanghai Rising Star
(15QA1401800), Professor of Special Appointment (Eastern
Scholar) at Shanghai Institutions of Higher Learning, and the
National Program for Support of Top-notch Young
Professionals.
desired aryl sulfides 2a in only 29% yield with aryl thioacetate
2a′′ in 50% yield (SI, Scheme S1a). Further, 47% of homo-
coupling product of 2a′ was isolated with only 25% of product
2a under standard conditions when aryl thioacetate 2a′′ was
subjucted to diaryliodonium salt 1a. However, intermediate
2a′′ and aryl iodide
5 could afford the desired product 2a in 88%
yield under standard conditions (SI, Scheme S1b). It illustrated
that aryl thioacetate is the key intermediate during sulfur-
iodine exchange process. Thus, a postulated reaction pathway
Notes and references
is depicted in Scheme 2. Intermediate
6
was afforded through
with Cu(I) species
1
2
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intermediate 10. Reductive elimination of 10 afforded desired
product 2 and regenerated Cu(I) catalyst (Scheme 2).
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