NCC Pincer Ni (II) Complexes Catalyzed Hydrophosphination of Nitroalkenes with Diphenylphosphine

Article abstract of DOI:10.1002/aoc.5954

An efficient NCC pincer Ni (II)-catalyzed hydrophosphination of nitroalkenes with diphenylphosphine has been developed. Under the optimized conditions, both (hetero)aromatic and aliphatic nitroalkenes were well tolerated, irrespective of electronic effect, to provide the corresponding products in up to 99% yield.

Full text of DOI:10.1002/aoc.5954

Received: 7 February 2020
DOI: 10.1002/aoc.5954
Revised: 10 June 2020
Accepted: 5 July 2020
C O M M U N I C A T I O N
NCC Pincer Ni (II) Complexes Catalyzed
Hydrophosphination of Nitroalkenes with
Diphenylphosphine
Jing Yan | Yan-Bing Wang | Senyao Hou | Linlin Shi | Xinju Zhu
Xin-Qi Hao | Mao-Ping Song
|
College of Chemistry, Zhengzhou
An efficient NCC pincer Ni (II)-catalyzed hydrophosphination of nitroalkenes
with diphenylphosphine has been developed. Under the optimized conditions,
both (hetero)aromatic and aliphatic nitroalkenes were well tolerated,
irrespective of electronic effect, to provide the corresponding products in up to
University, No. 100 of Science Road,
Zhengzhou, Henan, 450001, P. R. China
Correspondence
Xinju Zhu, College of Chemistry,
Zhengzhou University, No. 100 of Science
Road, Zhengzhou, Henan 450001, P. R.
China.
99% yield.
K E Y W O R D S
Email: zhuxinju@zzu.edu.cn
Hydrophosphination, NCC pincer Ni (II) complexes, Nitroalkenes
Mao-Ping Song College of Chemistry,
Zhengzhou University, No. 100 of Science
Road, Zhengzhou, Henan 450001, P. R.
China.
Email: mpsong@zzu.edu.cn
Funding information
National Natural Science Foundation of
China, Grant/Award Numbers: 21672192
and 21803059 and 21929101 and U1904212
1
| INTRODUCTION
Consequently, the combination of imidazoline and
NHC moieties around metal center enables generation
of efficient and stable catalysts with superior catalytic
reactivity.
Pincer complexes are important class of well-defined
structures supported by tridentate ligands, which
exhibits superior performance in catalytic transforma-
tions via suitable choice of transition metals as well as
fine modifications of steric and electronic effects of
ligands. Up to now, a series of NCN, PCP, NNC,
PNP, PNN, and other tridentate metal complexes have
been successfully synthesized through variations of
Organophosphorus compounds are versatile building
blocks in organic synthesis, pharmaceuticals, and mate-
[
6]
rials science.
Meanwhile, they served as important
[1]
ligands in transition-metal catalyzed and organocatalytic
[
7]
reactions.
Moreover, phosphorus moieties could
also be utilized as ortho-directing groups to facilitate
[2]
[8]
donor moieties.
recognized as representative nitrogen donor moieties,
In special, imidazolines have been
regioselective C-H activation. Recently, great effort has
[
3]
[9]
been made to prepare P-containing compounds, mainly
which have been utilized in Morita-Baylis-Hillman reac-
tions, alkynylation of trifluoropyruvates, alkylations of
phthalan, and sequential hydroboration/hydrogenation
including metal catalyzed cross-coupling of pre-
[
10]
functionalized arenes,
matics and other substrates,
C-H functionalization of aro-
and difunctionalization of
with various phosphorus pre-
[
11]
[4]
[12]
[13]
of internal alkynes. Recently, N-heterocyclic carbenes
alkenes
and alkynes
(
NHCs) have also demonstrated superior σ-donating
cursors. Among these categories, metal-catalyzed hydro-
phosphination of alkeneand alkynes represents an
[
5]
ability to form stable metal-NHC complexes.
Appl Organomet Chem. 2020;e5954.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
1 of 6
https://doi.org/10.1002/aoc.5954

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YAN ET AL.
1
3
efficient methodology for the preparation of
J = 7.2 Hz, 3H). C NMR (101 MHz, CDCl ) δ 168.7,
3
[14–16]
functionalized phosphorus products.
Specially, pin-
168.3, 144.3, 141.0, 137.8, 136.1, 135.1, 129.9, 129.1, 128.7,
127.3, 127.0, 126.6126.3, 123.2, 121.0, 120.5, 113.1, 110.5,
80.2, 72.1, 44.6, 21.1, 16.8. HRMS (positive ESI):
cer complexes catalyzed hydrophosphination of electron-
deficient alkenes with secondary phosphines has been
well established by the group of Duan, Leung, Pullarkat,
+
[M − Cl] calcd for C H N Ni 539.1746, found
33
29 4
[17–21]
Zhang, and Song groups.
Despite the above elegant
539.1735.
work, most of the reported systems rely on precious pal-
ladium metal. It is thus highly desirable to develop earth-
abundant metal catalyzed hydrophosphination.
2.2 | General procedure for the synthesis
of nitroalkenes (3a-r)
[24]
Our group has been interested in synthesizing novel
pincer-type complexes and exploring the corresponding
[17c,21]
catalytic activity.
Recently, we have also developed
To a stirred mixture of aldehyde derivatives (10 mmol)
and nitromethane (11 mmol) in methanol (5 ml) at
imidazoline- and imidazopyridine-based pincer com-
plexes, which exhibited good activity in Friedel-Crafts
alkylation, Suzuki-Miyaura reaction, transfer hydrogena-
ꢀ
0 C was added an aqueous solution of sodium hydrox-
ide (5 M, 4 ml) over a period of 30 min. The reaction
[22,23]
ꢀ
ꢀ
tions, and other applications.
As the continuation of
mixture was stirred at 0 C to 5 C for another 30 min.
After warmed to room temperature, the reaction
was completed in 1–12 hr, which was monitored by
TLC. Next, the reaction mixture was mixed with ice
water (2 ml) and poured over crushed ice containing
concentrated HCl (5 M, 10 ml). The yellow precipita-
tion was filtered, dried in a vacuum desiccator, and
crystallized from hot EtOH to give the corresponding
niroalkenes 3.
our previous work, we herein firstly developed NCC pin-
cer Ni (II) complex 2a catalyzed hydrophosphination of
nitroalkenes (Scheme 1).
2
2
| EXPERIMENTAL
.1 | Synthesis of complexes Ni
(II) complex 2 g
In a 25 ml two-necked Schlenk tube were added NCC
ligand precursor (0.25 g, 0.44 mmol), NaOAc (0.36 g,
2.3 | General procedure for
Hydrophosphination
4
.40 mmol), and NiCl2 (0.11 g, 0.77 mmol) in dry
DMAc (10 ml). The mixture was refluxed under an Ar
atmosphere for 48 hr. After removal of organic solvent,
the residue was purified by passing through a short col-
umn containing a layer of Celite and a layer of silica
with dichloromethane as the eluent. The desired prod-
ucts 2 g were purified once again by preparative TLC
on silica gel plates with CH Cl /EtOAc = 1/1 as
To a mixture of KOAc (1.96 mg, 10 μmol) and 2a (4.5 mg,
10 μmol) in 1,2,3-trichloropropane (2 ml) was added dip-
henylphosphine 4a (17.0 μL, 0.10 mmol) and the
ꢀ
resulting solution was stirred at −20 C for 30 min. After
addition of trans-β-nitrostyrene 3 (0.15 mmol), the solu-
ꢀ
tion was stirred at −20 C for 12 hr, followed by directly
oxidation by H O aqueous solution (30%, 40 μL). The
2
2
2 2
the eluent.
Yield: 17% (0.043 g). [α]
reaction mixture was warmed to room temperature and
stirred for another 2 hr. Then saturated NaCl aqueous
solution (0.15 ml) was added and the solution was
extracted with dichloromethane. The organic phase was
collected and dried over anhydrous Na SO . After
20
ꢀ
= +160 (c 0.25, CHCl ).
D
3
1
H NMR (400 MHz, CDCl ) δ 7.46 (d, J = 7.3 Hz, 2H),
3
7
.42–7.27 (m, 7H), 7.21 (d, J = 1.9 Hz, 1H), 7.07 (d,
J = 7.7 Hz, 2H), 7.01–6.90 (m, 2H), 6.72 (q, J = 7.5 Hz,
2
4
2H), 6.76 (d, J = 1.9 Hz, 1H), 6.27 (dd, J = 6.7, 1.6 Hz,
1H), 5.23 (d, J = 4.4 Hz, 1H), 4.70 (d, J = 4.5 Hz, 1H),
4.67 (m, 1H), 4.46 (m, 1H), 2.33 (s, 3H), 1.39 (t,
removal of organic solvent, the residue was purified by
silica gel chromatography using CH Cl /EA = 2/1 as
eluent to afford the product 5.
2
2
SCHEME 1 Ni (ll) complex 3a catalyzed
hydrophosphination of nitroalkenes

YAN ET AL.
3 of 6
3
3
| RESULTS AND DISCUSSION
.1 | Catalytic investigation
Initially, various base, such as t-BuONa, KOAc, NaOAc,
and Na CO , were employed, indicating NaOAc is the
2
3
best choice (Table 2, entries 1–4). Either increasing or
decreasing temperature is detrimental to reaction effi-
ciency (Table 2, entries 5 and 6). When the reaction was
performed under air, no corresponding product could be
detected, probably due to the oxygen sensitivity of the
Pincer Pd and Ni complexes 1 and 2 were prepared
according to previous report by our group.
[22a]
In addi-
tion, complex 2 g was new compound and fully charac-
terized. Our initial investigation started with
hydrophosphination of trans-β-nitrostyrene 3a with dip-
henylphosphine 4a in the presence of Pd and Ni com-
plexes (Table 1). To our delight, the desire product 5a
could be obtained in the range of 65–94% yield when dif-
ferent catalyst was employed. In general, Pd
[
18b]
phosphine group (Table 2, entry 7).
Next, various sol-
vent, including CH Cl , 1,2,3-trichloropropane, acetone,
2
2
THF, CH CN, and toluene, were examined (Table 2,
3
entries 8–13). When 1,2,3-trichloropropane was utilized,
product 5a could be obtained in up to 99% yield (Table 2,
entry 9). Finally, the molar ratio of 3a/4a was investi-
gated. Decreasing the molar ratio of 3a/4a to 1/1 led to
low reaction efficiency (Table 2, entry 14), while increas-
ing the molar ration of 3a/4a to 2/1 gave no increased
efficiency (Table 2, entry 15). More details of hydro-
phosphination investigation are provided in Supporting
Information (Tables S1-S4).
With the optimized conditions in hand, the substrate
scope of nitroalkenes and phosphines was investigated
(Scheme 2). Initially, aromatic nitroalkenes with substitu-
ents at the para-, meta-, and ortho-positions were
examined. Both electron-rich (OMe and Me) and
electron-deficient (F, Cl, and Br) substrates were well
(
II) complexes 1a-g demonstrates superior reactivity com-
pared with Ni (II) complexes 2a-g. For Pd (II) complexes,
b exhibited the best performance to afford 5a in 94%
1
yield (Table 1, entry 2), while Ni (II) complex 2a could
also provide 5a in 91% yield (Table 1, entry 8). Consider-
ing the low toxicity and inexpensiveness of Ni complex,
catalyst 2a was chosen for further evaluation. Meanwhile,
H O was added at the work-up step to obtain an oxide-
phosphine complex due to the oxygen sensitivity of the
phosphine group.
Subsequently, the effect of base, solvent, temperature,
and molar ratio was systematically evaluated (Table 2).
2
2
a
TABLE 1 Optimization of reaction conditions
Entry
Complex
Yield (%)
Entry
8
Complex
Yield (%)
1
2
3
4
5
6
7
1a
1b
1c
1d
1e
1f
92
94
91
92
81
89
93
2a
2b
2c
2d
2e
2f
91
75
64
77
65
71
78
9
10
11
12
13
14
1 g
2 g
a
ꢀ
Reaction conditions: 3a (0.15 mmol), 4a (0.10 mmol), pincer complex (10 mol%), NaOAc (10 mol%), CHCl
3
2 2
, −20 C, 12 hr; then H O (2.5
ꢀ
equiv), −20 C to r.t., 2 hr. Isolated yields.

4
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YAN ET AL.
a
TABLE 2 Optimization of reaction conditions
o
Entry
Solvent
Base
T [ C]
Yield (%)
91
1
2
3
4
5
6
CHCl
CHCl
CHCl
CHCl
CHCl
CHCl
CHCl
3
3
3
3
3
3
3
t-BuONa
KOAc
−20
−20
−20
−20
30
91
NaOAc
93
Na
2
CO
3
66
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
57
−40
−20
−20
−20
−20
−20
−20
−20
−20
−20
82
b
7
N.R.
90
8
2 2
CH Cl
9
1,2,3-Trichloropropane
99
10
11
12
13
14
15
Acetone
THF
77
61
CH
3
CN
79
Toluene
59
c
1,2,3-Trichloropropane
1,2,3-Trichloropropane
58
d
99
a
ꢀ
2 2
Reaction conditions: 3a (0.15 mmol), 4a (0.10 mmol), complex 2a (10 mol%), base (10 mol%), 12 hr; then H O (2.5 equiv), −20 C to r.t.,
2
hr. Isolated yields.
b
in the air.
c
d
3
a (0.10 mmol), 4a (0.10 mmol). 3a (0.20 mmol), 4a (0.10 mmol).
tolerated to afford the corresponding products 5a-l in
3–99% yields. The molecular structure of product 5 k
neutral nitro-nickel intermediate III with increased
[
26]
7
reactivity,
which might equilibrate with the zwitter-
was further confirmed by X-ray analysis, which is pro-
vided in Supporting Information (Figure S1 and
Table S5). Also, dimethoxy-substituted nitroalkene could
react with diphenylphosphine to provide 5 m in 77%
yield. Next, heteroaromatic and 2-naphthyl-substituted
nitroalkenes were also employed, which generated prod-
ucts 5n-p in 80–94% yield. Moreover, the current protocol
could be applied to aliphatic nitroalkenes to deliver prod-
ucts 5q and 5r in 81% and 87% yields, respectively.
Finally, bis (adamant-1-yl)phosphine was also proved to
be a suitable substrate, which reacted with nitroalkenes
to furnish the corresponding products 5 s-v in 40–80%
yields.
ionic Ni-phosphine complex IV. Finally, the protonolysis
of intermediate IV in the presence of HOAc would
provide the desired product 5a accompanied with
regeneration of reactive Ni species I.
4 | CONCLUSIONS
In conclusion, we have developed pincer Ni (II)-catalyzed
of 1,4-addition of diphenylphosphine to nitroalkenes,
generating the corresponding phosphinated products in
good to excellent yield. The current protocol exhibits
several
characteristics,
including
earth-abundant
On the basis of previous literatures, 17–21] a plausible
mechanism was proposed (Scheme 3). Initially, replace-
ment of chloride in Ni (II) complex 2a by OAc would
afford Ni-OAc complex I, which underwent
[
transition-metal, broad substrate scope, and high
efficiency.
ACKNOWLEDGMENTS
transphosphination reaction with Ph PH 4a to give Ni-
Financial support from the National Natural Science
Foundation of China (Grant Nos. 21672192, 21803059,
U1904212, and 21929101) is gratefully appreciated.
2
PPh complex II. Subsequently, nucleophilic attack of
2
[25]
nickel phosphide to nitroalkene 3a
would generate a

YAN ET AL.
5 of 6
SCHEME 3 Proposed mechanism
ORCID
Xinju Zhu https://orcid.org/0000-0003-1966-3480
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SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
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How to cite this article: Yan J, Wang Y-B,
Hou S, et al. NCC Pincer Ni (II) Complexes
Catalyzed Hydrophosphination of Nitroalkenes
with Diphenylphosphine. Appl Organomet Chem.
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