Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and Its Derivatives

Article abstract of DOI:10.1002/anie.201713333

A nickel(0)-catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a new atom- and step-economical approach to allylic amines by using alkenes instead of alkenyl-metallic reagents. Experiments and DFT calculations showed that TsNH₂ promotes the proton transfer from the coordinated olefin to the imine, accompanied by a new C?C bond formation.

Full text of DOI:10.1002/anie.201713333

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Accepted Article
Title: Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and
Derivatives
Authors: Qi-Lin Zhou, Li-Jun Xiao, Chao-Yue Zhao, Lei Cheng, Bo-Ya
Feng, Wei-Min Feng, Jian-Hua Xie, and Xiu-Fang Xu
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10.1002/anie.201713333
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Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and
Derivatives
Li-Jun Xiao,[a] Chao-Yue Zhao,[b] Lei Cheng,[a] Bo-Ya Feng,[b] Wei-Min Feng,[a] Jian-Hua Xie,[a] Xiu-Fang
Xu,*[b] and Qi-Lin Zhou*[a,c]
Abstract: We have developed a Ni(0)-catalyzed hydroalkenylation of
imines with styrene and derivatives. A wide range of aromatic and
aliphatic imines directly coupled with styrene and derivatives,
providing various synthetically useful allylic amines with up to 95%
yield. The reaction offers a new atom- and step-economical approach
to allylic amines by using abundant alkenes instead of alkenyl-metallic
reagents. Experiments and DFT calculations showed that the TsNH2
promotes the proton transfer from the coordinated olefin to imine,
accompanied by a new C–C bond formation.
remains a challenge.[10] Recently, Jia and co-workers developed
a Lewis acid-catalyzed direct coupling of styrene and derivatives
with highly-activated imines bearing two electron-deficient
groups,[11] providing allylic amines in atom-economical fashion
(Scheme 1c). However, the common aldimines are inert in the
reaction. Herein we report a nickel-catalyzed direct coupling of
aldimines with styrene and derivatives, producing allylic amines
(Scheme 1d). The presence of catalytic amount of TsNH2 proved
to be critical for the reaction efficiency. The experiments and
density functional theory (DFT) calculations showed that the
TsNH2 acts as a Brønsted acid to aid the ring opening of
nickellacycle and facilitates the coupling reaction.
Allylic amine moieties not only widely exist in a large number of
important naturally occurring nitrogen-containing compounds,
agrochemicals and pharmaceutical but also act as a versatile
building block in organic synthesis.[1] In this context, the
development of general and efficient methods for the synthesis of
allylic amines has been a topic of considerable interest.[2] Among
various potential methods, direct C–C coupling of imines and -
compounds represents one of the most attractive pathways
because it allows two smaller carbon skeletons to be joined
together, meaning that more abundant and inexpensive starting
materials could be used.[3] Traditional strategy for such couplings
mainly relies on nucleophilic additions of alkenylmetals to imines
(Scheme 1a), in which alkenylmetals are generally in situ
prepared from alkenyl halides[4] or alkynes[5] with organometallic
reagents. To avoid the use of sensitive alkenylmetals, some
alternative methods are developed. One is reductive coupling[6] or
alkylative coupling[7] of alkynes with imines in the presence of
various reductants or alkylmetallic reagents (Scheme 1b).
Another is the coupling of activated alkenes with imines such as
in the Morita–Baylis–Hillman reaction[8] and C–H addition
reaction[9]. Despite these progresses, the coupling of abundantly
available alkenes such as styrene and -olefins with imines
Scheme 1. The synthesis of allylic amines by C–C couplings of
imines with -compounds
The Ni(0)-catalyzed coupling reaction of -components and
carbonyls or imines is one of the most efficient protocols for their
join via C–C bond formation.[12] Jamison and co-workers
pioneered in achieving a Ni(0)-catalyzed coupling of aromatic
aldehydes with -olefins in the presence of Et3SiOTf and Et3N,
providing allylic alcohol silyl ethers.[13] We recently developed a
Ni(0)-catalyzed hydroacylation of alkenes with aldehydes,
delivering ketones.[14] When the aldehyde was switched into an
imine, surprisingly, we obtained a small amount of allylic amine,
instead of ketimine as expected. Encouraged by this result, we
decided to investigate the reaction of imines with alkenes in detail.
We found that the Ni(0) complexes with monophosphine
ligands catalyzed the hydroalkenylation of imine 2a with styrene
(1a) (Table 1, entries 1–6) and that PCy3 was the best ligand,
providing allylic amine 3a in 56% yield (entry 4). The use of
diphosphine ligands such as 1,2-bis(diphenylphosphaneyl)-
[a]
[b]
[c]
L.-J. Xiao, L. Cheng, W.-M. Feng, Prof. J.-H. Xie, Prof. Q.-L. Zhou
State Key Laboratory and Institute of Elemento-organic Chemistry
College of Chemistry, Nankai University
Tianjin 300071, China
E-mail: qlzhou@nankai.edu.cn
Homepage: http://zhou.nankai.edu.cn
C.-Y. Zhao, B.-Y. Feng, Prof. X.-F. Xu
Department of Chemistry, Key Laboratory of Advanced Energy
Materials Chemistry (Ministry of Education)
College of Chemistry, Nankai University
Tianjin 300071, China
E-mail: xxfang@nankai.edu.cn
Prof. Q.-L. Zhou
Collaborative Innovation Center of Chemical Science and
Engineering (Tianjin)
Tianjin 300071, China
Supporting information for this article is given via a link at the end of
the document.
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10.1002/anie.201713333
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ethane (dppe), 1,3-bis(diphenylphos-phaneyl)propane (dppp)
gave no reaction. To improve the yield of the hydroalkenylation
product, various additives were evaluated. In the presence of a
Brønsted acid, such as H2O, PhOH, the yield of allylic amine 3a
was slightly increased (entries 7–11). Surprisingly, the TsNH2
dramatically promoted the reaction. When 10 mol % TsNH2 was
added, the yield of 3a increased to 97% (entry 11).
alkenes reacted with 2a smoothly to give desired products 4k–4n
in 80–85% yield. It is worth noting that vinylsilanes were also
suitable substrates, affording useful silane-terminated allylic
amines 4o and 4p in moderate yields. However, the reactions of
aliphatic alkenes with aldimines produced a mixture of allylic and
homoallylic amines, and sometimes the homoallyic amine
became the main product (4q–4t).[15]
Table 1. Optimization of reaction conditions[a]
Table 2. Nickel-catalyzed hydroalkenylation of imines 2 with
styrene[a]
entry
1
ligand
PPh3
additive (mol%)
yield (%)[b]
‒
12
16
35
56
8
2
PPh2Cy
PPhCy2
PCy3
‒
3
‒
4
‒
5
PnBu3
PtBu3
PCy3
‒
6
‒
5
7
TfNH2 (10)
H2O (10)
PhOH (10)
PhCO2H (10)
TsNH2 (10)
TsNH2 (5)
TsNH2 (20)
33
62
60
51
97 (92)
84
74
8
PCy3
9
PCy3
10
11
12
13
PCy3
PCy3
PCy3
PCy3
[a] Reaction condition: 1a (1.0 mmol), 2a (0.5 mmol), toluene (1 mL). [b]
Determined by 1H NMR analysis using an internal standard.
Using the above-described optimal reaction conditions, we
evaluated a wide variety of aldimines 2 in the reaction with styrene
(Table 2). The protecting group on the imine N atom proved to be
necessary, and various frequently used protecting groups were
suitable, providing 81–92% yield (3a–3d). Aromatic aldimines
derived either from aromatic aldehydes bearing substituents with
various electronic and steric property (3e–3j), or from
heteroaromatic aldehydes (3k–3m), are suitable substrates,
affording the products in good to high yields (75%–96%). In
addition, we successfully carried out the reaction of aliphatic
aldimines, which are challenging substrates under traditional
addition reaction conditions owing to competing side-reactions
such as imine–enamine tautomerization, decomposition and self-
condensation. All the tested aliphatic aldimines bearing different
steric alkyl group gave the desired products in high yield (3n–3q,
85–95%). It was delighted to find that the ketimine, which often
displays extremely low reactivity in coupling reaction, can also
react with styrene, affording the allylic amine 3r with a tertiary
carbon in 50% yield.
[a] Isolated yield, TsF = 4-CF3C6H4SO2. [b] 4-CF3C6H4SO2NH2 (10
mol%) was added.
To gain mechanistic insight into the hydroalkenylation reaction,
we carried out control experiments. When 10 mol % NiBr2(dme)
and 20 mol % PCy3 were used as catalyst, no reaction occurred
under standard reaction conditions. However, when Zn (40
mol %) was added as a reductant, the hydroalkenylation reaction
proceeded in high yield (92%) (Scheme 2a). This result indicated
that the reaction was catalyzed by Ni(0) instead of Ni(II). We found
that the yield of hydroalkenylation reaction in the absence of
TsNH2 can be increased from 56% (Table 1, entry 4) to 96% by
prolonging reaction time to 24 h. We speculated that a trace
amount of TsNH2 was produced by hydrolysis of imine 2a in the
reaction, which promotes the reaction. To confirm that, we
conducted the hydroalkenylation reaction with cyclic ketimine 2s
(Scheme 2b), which is stable and difficult to produce TsNH2 by
hydrolysis. Without adding TsNH2, only trace amount of
hydroalkenylation product was observed even in the presence of
Next, we investigated various alkenes 1 in the reaction with
benzaldimine 2a (Table 3). Aryl alkenes bearing substituents with
various steric and electronic property provided corresponding
products 4a–4j in high yields (80–95%). In addition, the heteroaryl
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H2O. However, by adding 10 mol% TsNH2, the hydroalkenylation
product was obtained in 42% yield. These results suggested that
the presence of catalytic amount of TsNH2 is critical for the
reaction.
Table 3. Nickel-catalyzed hydroalkenylation of imine 2a with
alkenesa
Scheme 2. Control experiments and proposed TsNH2’s role
To understand the reaction mechanism, DFT study was
performed using the reaction of imine 2a with styrene.[18] As
shown in Figure 1, the substrate-coordinated complex A1
undergoes oxidative cyclization to form the azanickellacycle
intermediate B1 through transition state TS1. Then, the reaction
can proceed along three distinct pathways: direct -hydride
elimination of B1 via transition state TS6 (in red); H2O promoting
the ring-opening of B1 via transition state TS4 (in blue); and
TsNH2 promoting the ring-opening of B1 via transition state TS2
(in black). TS2 is more stable than TS4 and TS6 by lowering the
overall barrier of the catalytic cycle to 30.9 kcal/mol, which means
that the rate-limiting step is the oxidative cyclization. The KIE
study (kH/kD = 1.1, see SI for details) also showed that the
hydrogen transfer process is not involved in rate-limiting step.
In summary, we have developed a protocol for direct
[a] Isolated yield, TsF = 4-CF3C6H4SO2. [b] 10.0 equiv. of 1o (neat). [c] 4-
CF3C6H4SO2NH2 (10 mol%) was added. [d] 5.0 equiv. of alkene 1. [e] Yield of
mixture of two isomers; A/H = ratio of allylic amine to homoallylic amine; The
E/Z-selectivity was determined by coupling constant of the olefinic hydrogens in
NMR spectra,16 and only E isomer was observed.
hydroalkenylation of imines with alkenes catalyzed by
a
Ni(0)/PCy3 complex. This protocol offers a straightforward method
for the synthesis of allylic amines. The alkenes function like the
alkenylmetal reagents that are used in conventional methods for
the synthesis of allylic amines. The experimental and
computational studies showed that the TsNH2 promotes ring-
opening of azanickellacycle intermediate and facilitates the proton
transfer from olefin to imine. Further investigations on the
asymmetric version of the reaction and its applications in organic
synthesis is in progress in our laboratory.
A plausible reaction path is proposed in Scheme 2c based on
the aforementioned experimental results and previous reports[17]
.
Oxidative cyclization of imine and alkene resulted in the formation
of a five-membered azanickellacycle intermediate I. The Brønsted
acid TsNH2 promoted the ring-opening of azanickellacycle to the
intermediate II through protonation to the N atom and coordination
to the Ni atom in the azanickellacycle. Subsequent -hydride
elimination of the intermediate II would be feasible to release an
allylic amine product and regenerate the nickel catalyst and
TsNH2.
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stir bar, Ni(cod)2 (14 mg, 0.05 mmol), PCy3 (28 mg, 0.1 mmol), TsNH2 (0.05
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product.
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Acknowledgements
We thank the National Natural Science Foundation of China (Nos.
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Keywords: Nickel Catalyst • hydroalkenylation • Imine• Alkene •
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Li-Jun Xiao, Chao-Yue Zhao, Lei Cheng,
Bo-Ya Feng, Wei-Min Feng, Jian-Hua Xie,
Xiu-Fang Xu*, and Qi-Lin Zhou*
Page No. – Page No.
Nickel(0)-Catalyzed Hydroalkenylation
of Imines with Styrene and Derivatives
A Ni(0)-catalyzed hydroalkenylation of imines with styrene and derivatives is reported.
The reaction offers a new atom- and step-economical approach to allylic amines by
using abundant alkenes instead of alkenylmetal reagents.
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