Ni-Catalyzed Dimerization and Arylation of Diarylacetylenes with Arylboronic Acids

Article abstract of DOI:10.1021/acs.orglett.7b03398

A new, facile, and efficient protocol for the synthesis of polysubstituted conjugated 1,3-dienes through Ni-catalyzed tandem dimerization/cross-coupling reaction of diarylacetylenes and arylboronic acids in the presence of a catalytic amount of B₂pin₂ has been developed. A series of arynes and arylboronic acids with different substituents participated well in this catalytic system, affording a variety of useful conjugated 1,3-dienes.

Full text of DOI:10.1021/acs.orglett.7b03398

Letter
Cite This: Org. Lett. XXXX, XXX, XXX−XXX
pubs.acs.org/OrgLett
Ni-Catalyzed Dimerization and Arylation of Diarylacetylenes with
Arylboronic Acids
Yang Liu, Guoying Zhang, and Hanmin Huang*,†,‡
†
,§
†
†State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of
Sciences, Lanzhou 730000, P. R. China
‡
Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China
§University of Chinese Academy of Sciences, Beijing 100049, P. R. China
*
S Supporting Information
ABSTRACT: A new, facile, and efficient protocol for the synthesis of
polysubstituted conjugated 1,3-dienes through Ni-catalyzed tandem dimeriza-
tion/cross-coupling reaction of diarylacetylenes and arylboronic acids in the
presence of a catalytic amount of B pin has been developed. A series of arynes
2
2
and arylboronic acids with different substituents participated well in this
catalytic system, affording a variety of useful conjugated 1,3-dienes.
he conjugated 1,3-dienes are an important class of
As active organic electrophiles, alkynes have been used as
T
molecules which are prevalent in a variety of biologically
coupling partners for the Ni-catalyzed cross-coupling reac-
1
11
active natural compounds and pharmaceuticals. Due to their
unique reactivities, they are also vital building blocks for the
tions. In 2015, our group reported a Ni-catalyzed reductive
tetramerization of diarylacetylenes with B pin as an environ-
2
2
2
12
synthesis of diverse carbocycles, heterocycles, and lactams.
mental and efficient reductant. Mechanistic studies disclosed
that the five-membered nickelacycle species was involved as a
Several common synthetic approaches including olefination of
3
carbonyl compounds, transition-metal-catalyzed cross-cou-
key intermediate. Based on the resulting mechanistic insight
4
9d,12,13
pling reactions, rearrangement, reduction, and metathesis of
and inspired by previous reports,
we reasoned that the
5
enynes, as well as the Wittig reactions of allylic phosphonium
alkenyl-Ni species would be transferred to the desired
polysubstituted dienes with arylboronic acids (Scheme 1).
6
ylides with aldehydes have been developed with the aim of
gaining conjugated dienes. Generally, linear dienes such as A
can be prepared easily, whereas synthesis of polysubstituted
conjugated dienes, such as B, which are a kind of efficient
luminescent material processing various potential applications,
Scheme 1. Strategies for Synthesis of Polysubstituted Dienes
7
,8
is more challenging (Figure 1). Several common methods to
Herein, we report a Ni-catalyzed tandem dimerization/cross-
coupling reaction of diarylacetylenes with arylboronic acids,
providing an efficient method to prepare a series of
polysubstituted conjugated 1,3-dienes.
Figure 1. Linear (A) and polysubstituted (B) diene.
At the start of our studies, we used 1,2-diphenylethyne (1a)
and (4-methoxyphenyl)boronic acid (2a) as the model
substrates to test the viability of our hypothesis, and the
reaction was performed at 120 °C for 12 h. To our delight, the
prepare the polysubstituted conjugated dienes, such as dienyl
rearrangement, alkaline desilylation, allene isomerization, and
5e,9
aryne dimerization, have been reported.
However, those
approaches almost always involve noble metal catalysts such as
8c,9e
9b,c
5e
reaction smoothly took place in the presence of Ni(COD) and
2
Pd,
Au,
Ru which are sensitive to air and moisture,
gave the desired product 3aa in 31% yield (Table 1, entry 1).
leading to not only difficult operation, but also high cost.
Hence, it is desirable and challenging to explore inexpensive
and green reagents as well as efficient methods to prepare the
polysubstituted conjugated 1,3-dienes.
However, Ni(COD) is not only expensive, but also sensitive to
2
air and moisture. Therefore, we wished to use cheap, stable Ni-
precursor and environmental B pin as catalyst and reductant,
2
2
Ni-catalyzed reductive cross-coupling reactions between two
organic electrophiles have emerged as effective methods for C−
Received: November 1, 2017
10,11
C bond construction and have drawn increasing attention.
©
XXXX American Chemical Society
A
DOI: 10.1021/acs.orglett.7b03398
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
a
Table 1. Optimization of Reaction Conditions
°C for 6 h (Table 1, entries 16−20). It is worth mentioning that
the reaction is highly selective: only (1Z,3Z)-isomer 3aa was
observed in all cases.
With the optimized reaction conditions identified, the
generality of the Ni-catalyzed cross-coupling reaction of
diarylacetylenes with arylboronic acids was investigated. The
scope of the arylboronic acids was first examined by the
adoption of 1,2-diphenylethyne as the coupling partner, and the
results are summarized in Table 2. Various arylboronic acids
entry
[Ni]
B pin (equiv)
solvent
yield (%)
2
2
1
2
3
4
5
6
7
8
9
Ni(COD)2
0
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
MeOH
EtOH
31
<5
0
NiSO4
0.5
0.5
0.5
0.5
0.5
0.3
0.2
0.1
0.05
0.3
0
NiBr2
a
Ni(NO3)
2
17
64
80
78
66
44
18
0
Table 2. Substrate Scope of Arylboronic Acids and Arynes
Ni(COD)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
entry
Ar
Ar
Ar′
yield (%)
10
11
12
13
14
15
16
17
18
19
20
1
2
3
4
5
6
7
8
9
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
4-OCH
3-OCH
C
C
H
H
3aa (82)
3ab (62)
3ac (77)
3ad (70)
3ae (63)
3af (65)
3ag (78)
3ah (72)
3ai (65)
3aj (60)
3ba (63)
3ca (74)
3da (49)
3ea (62)
3fa (58)
3ga (70)
3ha (72)
3ia (31)
3
6
4
4
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
Ni(OAc)2
0
3
6
0.3
0.3
0.3
0.3
0.3
0.3
0.3
0.3
40
30
<5
81
82
75
81
72
4-OCF
Ph
C H
3 6 4
n
PrOH
iPrOH
MeOH
MeOH
MeOH
MeOH
MeOH
3-CH
C
H
6
3
4
b
c
d
e
f
4-CH C H
3
6
4
3,5-(CH ) C H
3
3
2
6
6
4-FC H4
6
3-FC H4
1
0
6
4-ClC H4
a
11
3-CH C H
3-CH C H
4-OCH C H
3 6
3
6
4
3
6
4
4
4
4
4
4
4
4
4
General conditions: 1a (178 mg, 1.0 mmol), 2a (182 mg, 1.2 mmol),
Ni] (0.05 mmol, 5 mol %), solvent (2.0 mL), 120 °C, 12 h, isolated
1
1
2
3
4-CH C H
4-CH C H
4-OCH C H
3 6
[
3
6
4
3
6
4
b
c
d
e
f
3-OCH C H
3-OCH C H
4-OCH C H
yield. 120 °C, 18 h. 120 °C, 6 h. 120 °C, 3 h. 150 °C, 6 h. 90 °C,
3
3
6
4
4
3
3
6
4
4
3
6
6
h.
14
4-OCH
C
H
6
4-OCH
C
H
6
4-OCH
C
3
H
6
15
16
17
18
3,5-(CH ) C H
3,5-(CH ) C H
4-OCH C H
3 6
3
2
6
3
3
2
6
3
4-FC H4
4-FC H4
4-OCH C H
3 6
6
6
respectively, to optimize the reaction conditions. First,
screening of the Ni precursors revealed that Ni(OAc) gave
the best result. When the reaction was catalyzed by Ni(OAc)2
in the presence of 0.5 equiv of B pin in MeOH at 120 °C for
2 h, the desired product 3aa was isolated in 80% yield as a
single regio- and stereoisomer (Table 1, entry 6). Several other
Ni catalysts, such as NiSO , NiBr , and Ni(NO ) , showed
b
b
Ph
Ph
4-CH C H
4-OCH C H
3 6
3
6
4
2
CH3
4-OCH C H
3 6
a
General conditions: 1 (1.0 mmol), 2 (1.2 mmol), Ni(OAc) (0.05
2
2
2
mmol, 5 mol %), B pin (0.3 mmol), MeOH (2.0 mL), 120 °C, 6 h,
2
2
1
b
isolated yield. 3ha and 3ia were a mixture of regioisomers.
4
2
3 2
much lower catalytic activities under the same reaction
containing both electron-rich and electron-deficient functional
groups on the phenyl ring participated well in this catalytic
reaction, affording the desired product in good yields. Typical
functional groups such as methyl, methoxy, fluoro, chloro, and
trifluoromethoxyl were well tolerated under the reaction
conditions. For instance, the substrates with electron-rich
groups at the para- or meta-position on the phenyl ring
proceeded smoothly to afford the corresponding products in
good yields (Table 2, entries 1−7). Furthermore, the substrates
bearing electron-deficient halogen groups, such as F and Cl, on
the meta- or para-position of the phenyl ring were also
transformed into the desired products under the standard
conditions (Table 2, entries 8−10). Meanwhile, disubstituted
arylboronic acid was also a suitable substrate which worked well
in the reaction and provided the desired product 3ag in 78%
yield (Table 2, entry 7). Unfortunately, substrates with strong
conditions (Table 1, entries 2−4). It is worth noting that the
reaction proceeded smoothly with Ni(COD) as catalyst in the
2
presence of B pin and afforded 3aa in 64% yield, which
2
2
indicated that B pin played an important role in this catalytic
2
2
system. Additionally, the impact of B pin over the reactivity of
2
2
this reaction was investigated, and it was found that the loading
of B pin was crucial to obtain good yields (Table 1, entries 6−
2
2
1
0
0). Furthermore, when the loading of B pin was decreased to
.1 equiv, a moderate yield was still obtained. It is important to
2 2
mention that no desired product was observed under identical
conditions in the absence of B pin or Ni(OAc) (Table 1,
2
2
2
entries 11 and 12). During the exploration of the ligand effects
for this reaction, we discovered that the reaction was virtually
stopped when phosphine ligand was introduced into the
catalytic system (see the Supporting Information). Further
optimization of the reaction conditions revealed that the choice
of alcohol solvent was vital to the present catalytic system.
Screening of some representative alcohols demonstrated that
the most efficient catalysis was furnished in MeOH, affording
the desired product in 78% isolated yield (Table 1, entries 7
and 13−15). Finally, the effects of time and temperature on the
reaction were also investigated; the best result could be
obtained in 82% yield when the reaction was conducted at 120
electron-withdrawing groups such as CN, CF , and substrates
3
with substituents on the ortho-position of the phenyl ring were
not applicable in this transformation.
Next, the scope of various diarylacetylenes was examined for
this reaction. As shown in Table 2, diarylacetylenes bearing
electron-rich functional groups proceeded well to give the
corresponding products in good yields. For instance, the
substrates with electron-rich functional groups such as CH and
3
B
DOI: 10.1021/acs.orglett.7b03398
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
OCH3 were compatible with the present catalytic system
Scheme 2. Plausible Reaction Mechanism
(Table 2, entries 11−15). In addition, the fluorine substituted
diarylacetylene 1g also proceeded smoothly during this cross-
coupling reaction (Table 2, entry 16), whereas the substrates
with strong electron-withdrawing functional groups including
Cl, Br, CF were not applied in this reaction. Meanwhile, the
3
steric hindrance on the benzene ring of diarylacetylenes had a
slight effect on the reactivities (Table 2, 3ba vs 3ca, 3da vs
3
ea). Furthermore, the unsymmetrical arynes could also work
well under the present catalytic system and gave the desired
product 3ha and 3ia, but with lower regioselectivities (Table 2,
entries 17 and 18). Finally, the structure of 3ae was confirmed
by single-crystal X-ray analysis, and other products were
tentatively assigned by analogy.
In addition, we were pleased to find that the product 4a was
obtained in 46% yield in the presence of 1 equiv of B pin2
2
under similar reaction conditions (Table 3, entry 1). Mean-
Table 3. Ni-Catalyzed Reaction of Diarylacetylenes with
B2pin2
a
the active catalyst for the next catalytic cycle. On the other
hand, the intermediate II could also react with B pin in the
2
2
absence of arylboronic acid by transmetalation to produce
intermediate IV, which underwent reductive elimination to
afford 4aa.
In summary, we have successfully developed a new, facile,
and efficient method for the preparation of polysubstituted
conjugated 1,3-dienes through a Ni-catalyzed tandem dimeriza-
tion/cross-coupling reaction of diarylacetylenes with arylbor-
onic acids in the presence of B pin . A series of arynes and
arylboronic acids with different substituents proceeded well in
the catalytic system, affording a variety of useful conjugated 1,3-
dienes. In view of the readily available starting materials and
simple operation, this method may become a useful protocol
for the synthesis of polysubstituted conjugated 1,3-dienes.
Further investigations on application of products and detailed
mechanism of this reaction are currently underway in our
group.
entry
Ar
Ar
yield (%)
4a (46)
1
2
3
4
Ph
3-CH C H
Ph
3-CH C H
5a (40)
5b (30)
5c (37)
5d (32)
5e (36)
4b (32)
4c (44)
4d (38)
4e (48)
3
6
4
4
3
6
4
4
4-CH C H
4-CH C H
3
6
3
6
2
2
4-FC H4
4-FC H
6
6
4
b
5
Ph
4-CH C H
3 6
4
a
General conditions: 1 (1.0 mmol), B pin (1.0 mmol), Ni(OAc)
2
2
2
(
0.05 mmol, 5 mol %), MeOH (2.0 mL), 120 °C, 9 h, isolated yield.
b
4
e and 5e were the mixture of regioisomers.
while, the diphenylethyne dimerization reaction occurred in
this reaction and afforded the corresponding 5a in 40% yield as
a mixture with different stereoisomers. Further optimization of
this reaction parameters, such as temperature, time, solvents
and ligands, did not significantly improve the selectivity (see
the SI). Subsequently, we investigated several simple diary-
lacetylenes, and the results are shown in Table 3. Obviously, the
ASSOCIATED CONTENT
Supporting Information
■
*
S
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.or-
glett.7b03398.
substrates with functional groups, such as CH and F, could
3
participate the present catalytic system, affording the
corresponding products in the range of 32%−44% yields
Experimental procedures and compound characterization
data (PDF)
(
Table 3, entries 2 and 3). Moreover, the unsymmetrical
diarylacetylene also gave the desired product 4e in 48% yield
with lower regioselectivity (Table 3, entry 5). Finally, the
structure of 4c and one isomer of 5a were further validated by
single-crystal X-ray diffraction analysis.
Accession Codes
CCDC 1582910−1582912 contain the supplementary crystal-
lographic data for this paper. These data can be obtained free of
charge via www.ccdc.cam.ac.uk/data_request/cif, or by email-
ing data_request@ccdc.cam.ac.uk, or by contacting The
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
9d,12,13
On the basis of the above results and previous reports,
a plausible reaction pathway for the Ni-catalyzed cross-coupling
reaction of diarylacetylenes and arylboronic acids is proposed in
Scheme 2. Initially, reduction of Ni(II) precatalyst by B pin2
2
gave a catalytically active Ni(0) species. Subsequently, the
Ni(0) species could undergo oxidative cycloaddition with
diphenylethyne (1a) to generate five-membered nickelacycle I,
followed by protonation with MeOH to produce the key
intermediate II. The crowded environment promotes the Ni-
mediated cis−trans isomerization to form intermediate II. The
consequent transmetalation of II with arylboronic acid (2a)
took place to form intermediate III. Then, reductive
elimination of III gave the desired product 3aa and regenerated
AUTHOR INFORMATION
Corresponding Author
■
*
E-mail: hanmin@ustc.edu.cn.
ORCID
13
Hanmin Huang: 0000-0002-0108-6542
Notes
The authors declare no competing financial interest.
C
DOI: 10.1021/acs.orglett.7b03398
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
(
9) (a) Yamaguchi, S.; Endo, T.; Uchida, M.; Izumizawa, T.;
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Innovation Team and the National Natural Science Foundation
of China (21672199).
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