Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

Article abstract of DOI:10.1021/acs.orglett.0c01183

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

Full text of DOI:10.1021/acs.orglett.0c01183

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Letter
Palladium-Catalyzed Cascade Decarboxylative Amination/6-endo-
dig Benzannulation of o‑Alkynylarylketones with N‑Hydroxyamides
To Access Diverse 1‑Naphthylamine Derivatives
Youpeng Zuo, Xinwei He,* Qiang Tang, Wangcheng Hu, Tongtong Zhou, and Yongjia Shang*
Cite This: https://dx.doi.org/10.1021/acs.orglett.0c01183
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ABSTRACT: An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-
catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad
range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to
give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with
benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.
Scheme 1. Transition-Metal-Catalyzed Intermolecular and
Intramolecular Benzannulations for Construction 1-
Naphthylamine Skeleton
ompounds incorporating a naphthalene ring structure
exist in a broad array of both natural products and
C
bioactive molecules, which have been found to exhibit a wide
spectrum of biological activities.1 Among them, 1-naphthyl-
amines represent an important class that is found in key
structural frameworks of numerous biologically active mole-
cules and functional materials.2 As a consequence, great effort
has been devoted to developing efficient protocols for their
preparation.3 Intermolecular and intramolecular benzannula-
tions have attracted considerable attention as the efficient and
reliable synthetic tool for the synthesis of 1-naphthylamines in
a single operation (Scheme 1a).4 Very recently, Liu and co-
workers developed the copper- or nickel-catalyzed intra-
molecular benzannulation of o-allenylaryl nitriles for the
synthesis of 3-boryl/aryl-1-naphthylamine derivatives (Scheme
1b).5 Li’s group reported a AgNO3-catalyzed cycloisomeriza-
tion of o-alkynylphenyl enaminones for the synthesis of 4-acyl-
1-naphthylamine derivatives (Scheme 1c).6 Wang and co-
workers disclosed an intermolecular annulation of β-
enaminonitriles with alkynes via Rh(III)-catalyzed C−H
activation to construct highly substituted 1-naphthylamines
(Scheme 1d).7 In 2019, Zhou and coauthors found that amides
could be used as aminating agents, which were excellent
alternatives to toxic and/or odorous amines, and they
developed an efficient, convenient, and general method to
directly synthesize the valuable functionalized 1-naphthyl-
amines from readily available terminal alkynes, 2-bromoaryl
ketones, and amides via copper-catalyzed benzannulation in a
Received: April 2, 2020
https://dx.doi.org/10.1021/acs.orglett.0c01183
© XXXX American Chemical Society
Org. Lett. XXXX, XXX, XXX−XXX
A

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Letter
green solvent (Scheme 1e).8 In addition, copper-catalyzed
aminobenzannulation of ortho-alkynylarylketones with amines
has been described by Wen’s and Hua’s group, respectively.9
Consequently, the development of new efficient strategies that
provide straightforward access to highly functionalized 1-
naphthylamines is of significant importance.
a
Table 1. Optimization of the Reaction Conditions
b
entry
catalyst
base
solvent
temp/°C yield/%
It has been well established that ortho-alkynyl aryl carbonyl
species are competent reactants endowed with multiple
reactive sites, thus they have been widely served as versatile
precursors for many important targets of chemical and
biomedical potentials, allowing them to undergo a variety of
transformations, such as nucleophilic additions and Diels−
Alder reactions.10 As a member of the family of o-alkynyl aryl
carbonyl compounds, o-alkynylarylketones also attract great
interest within the scientific community.11 It is well-known that
o-alkynyl aryl ketones preferentially undergo the Lewis/
Brøsted acid induced intramolecular 5-exo-dig and 6-endo-dig
oxocyclization to form a variety of biological isobenzofuran
isobenzopyran derivatives12 as well as carbocyclization to
c
1
Pd(OAc)2
Pd(PPh3)4
Pd2(dba)3
−
NaOAc
NaOAc
NaOAc
NaOAc
−
CsOAc
AgOAc
KOAc
NaHCO3
Na2CO3
K2CO3
Et3N
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
NaOAc
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
PhCl
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
reflux
50
refulx
refulx
refulx
refulx
refulx
refulx
refulx
68
94
74
nr
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
Pd(PPh3)4
nr
81
85
87
54
57
15
37
51
trace
trace
29
53
68
92
48
48
92
41
86
48
94
70
prepare the useful 1-indanone and 1-naphthol skeletons.13
A
DMF
literature survey indicated that the synthesis of 1-naphthyl-
amine derivatives via the cascade reaction starting from 6-endo-
dig carbocylization using the o-alkynylarylketones, to the best
of our knowledge, remains rare. Herein, we report the first
palladium-catalyzed cascade decarboxylative amination/6-endo-
dig benzannulation of o-alkynylarylketones with N-hydroxya-
mides, which provides an efficient protocol for highly
functionalized 1-naphthylamine derivatives (Scheme 1f).
Initially, by using the Pd(OAc)2/PPh3 as a catalyst system,
the reaction of 1-(2-(phenylethynyl)phenyl)ethan-1-one (1a)
and N-hydroxybenzamide (2a) was performed in the presence
of NaOAc as an additive in toluene, and the desired product
3aa was isolated in 68% yield (Table 1, entry 1). Encouraged
by this result, we further examined the reactivity in other
palladium catalysts (Table 1, entries 2, 3). To our delight,
compound 3aa was generated in 94% yield when Pd(PPh3)4
was used as a catalyst in the absence of ligand. Control
experiments proved that the presences of Pd(PPh3)4 and base
were both mandatory for the formation of 3aa (Table 1, entries
4, 5). Next, various common inorganic and/or organic bases
were investigated to modulate the product formation (Table 1,
entries 5−11), and sodium acetate (NaOAc) was proven to be
the best choice. Afterward, the solvent effect was also evaluated
(Table 1, entries 12−17), and toluene was finally proven to be
the optimal solvent for the formation of compound 3aa.
Further optimization of the reaction conditions indicated that a
5 mol % Pd(PPh3)4/1.0 equiv of NaOAc catalyst system was
sufficient to promote this cascade reaction (Table 1, entry 2).
With the optimized reaction conditions in hand, we then
started to investigate the N-hydroxyamides for this cascade
decarboxylative amination/6-endo-dig benzannulation process
with 1-(2-(phenylethynyl)phenyl)ethan-1-one (2a). As shown
in Table 2, both alkyl and aryl N-hydroxyamides were well
proceeded under the optimal conditions, giving the desired
products 3 in moderate to excellent yields (68−94%)
regardless of their substitution patterns and electronic natures.
Electron-rich (4-OMe), electron-neutral (4-Me, 4-tBu, 3-Me)
and electron-deficient (4-F, 4-Cl, 4-Br, 4-CF3, 3-Br) N-
hydroxyl aryl amides provided the corresponding products
(3aa−3am) in moderate to excellent yields. It was particularly
that sterically hindered N-hydroxyl arylamides were success-
fully coupled with 1a and generated mono- and di-ortho-
substituted N-phenylnaphthalen-1-amines in 75−88%yields
MeNO2
MeCN
DCE
THF
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
d
21
22
23
24
25
26
27
e
f
g
h
i
j
a
Reaction conditions: 1-(2-(phenylethynyl)phenyl)ethan-1-one 1a
(0.25 mmol), N-hydroxybenzamide 2a (0.3 mmol), solvent (3 mL),
catalyst (5 mol %), and base (1.0 equiv) under an argon atmosphere
for 8 h. Ioslated yields. PPh3 used as ligand. The catalyst loading
was 2.5 mol %. The catalyst loading was 10 mol %. The base loading
was 0.5 equiv. The base loading was 2.0 equiv. Reaction time for 4
b
c
d
e
f
g
h
i
j
h. Reaction time for 16 h. 1 equiv of 2a was used.
(Table 2, 3aj, 3al, 3an, 3ao, and 3aq, respectively).
Encouragingly, disubstituted N-hydroxybenzamide, N-hy-
droxy-2-phenylacetamide, and N-hydroxylnaphthamides were
also compatible with this palladium-catalyzed cascade trans-
formation with good yields (Table 2, 3ap, 3ar−3at).
Interestingly, N-hydroxyl alkyl amides, such as t-butyl,
cyclohexyl, and adamantly, gave the desired products 3au,
3av, and 3aw in 85%, 89%, and 76% yields, respectively.
Moreover, the structure of compound 3aq was unambiguously
characterized via single crystal X-ray crystallographic analysis
(see the Supporting Information, for details).
We subsequently examined the structural diversity of various
o-alkynylarylketones 2 by assessing the substitution effect on
both the two benzene rings and R4 substituent. First, substrates
R2 with a broad range of substitution were examined.
Substituents including electron-donating groups (−OMe,
−Me) and electron-withdrawing groups (−F, −Cl, −CF3) at
the 4-, 5-, and 6-positions of the benzene rings were well
tolerated, affording the corresponding products 3ba−3ma in
good to excellent yields. No significant effect was observed
when altering the position of the fluoro group (3da, 3ha, and
B
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Letter
a b
,
Table 2. Substrate Scope of N-Hydroxyamides 1
Table 3. Scope of Diverse o-Alkynylarylketones for the
a b
,
Palladium-Catalyzed Cascade Reactions
a
Reaction conditions: unless otherwise specified, 1-(2-
(phenylethynyl)phenyl)ethan-1-one 2a (0.25 mmol), N-hydroxya-
mide 1 (0.3 mmol, 1.2 equiv), Pd(PPh3)4 (5 mol %), and NaOAc (1.0
equiv) in toluene (3 mL) under an argon atmosphere at 100 °C for 8
a
Reaction conditions: unless otherwise specified, (o-phenylethynyl)-
arylketones 2 (0.25 mmol), N-hydroxybenzamide 1a (0.3 mmol),
Pd(PPh3)4 (5 mmol %), and NaOAc (1.0 equiv) in toluene (3 mL)
b
h. Isolated yields.
b
under argon atmosphere at 100 °C for 8 h. Isolated yield.
3la showed 86%, 82%, and 92% yields, respectively). Reaction
with electron-rich o-alkynylarylketones smoothly afforded the
desired products 3na and 3oa in 94% and 92% yields,
respectively. The same results were then observed with R3
substituents bearing both electron-donating groups (−Me,
−Et, −OMe) and electron-withdrawing groups (−F, −Cl, −Br,
−CF3) at the phenyl rings regardless of their substitution
positions (Table 3, 3pa−3za). Moreover, the phenyl group
could be replaced by isopropyl or ferrocenyl, leading to the
desired 1-naphthylamines 3b′a and 3c′a in 68% and 86%
yields, respectively. Additionally, we turned our attention to
studying the suitability of the substituent R4 (changing methyl
to ethyl or acetyl ethyl ester group), and the desired products
3d′a and 3e′a were successfully obtained in 88% and 86%
yields, respectively.
Scheme 2. Further Studies
To further amplify the substrate diversity, nonaromatic
acetylenone, such as 3,5-eneynic ketone, was deployed for this
palladium-catalyzed cascade reaction. The isolated product was
the intramolecular 5-exo-dig oxocyclization rather than the
desired diphenylamine 5, and the isolated yield is 75% yield
(Scheme 2a). Next, the feasibility of the palladium-catalyzed
three-component reaction of 2-haloaryl ketones (6: X = Br and
7: X = I), phenylacetylene 8, and N-hydroxybenzamide 1a was
investigated, affording the desired product 3aa in 15% and 34%
yields, respectively (Scheme 2b). In addition, the reaction
between o-alkynylarylketone 1a with N-hydroxyamide 2a was
scaled up to 40 times under the standard conditions. The
C
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corresponding product 3aa was afforded on a gram-scale
without reducing the percentage yield (Scheme 2c). To
showcase the synthetic utilities, product 3aa was used for late-
stage transformation. In the presence of sodium hydride, N-
methylation between compound 3aa and iodomethane easily
generated N,N-disubstituted 1-naphthylamine derivative 9aa in
92% yield (Scheme 2d), highlighting the synthetic utility of the
current protocol.
in Scheme 4. Initially, the condensation of substrate 1 and 2 to
generates the intermediate A. Meanwhile, the oxidative
Scheme 4. Proposed Mechanism
To gain some mechanistic insights into the present protocol,
several control experiments were performed (Scheme 3). To
Scheme 3. Mechanistic Studies
addition of N-hydroxyamide 2 to the Pd(0) catalyst generates
the Pd(II) catalyst. Subsequently, the coordination of Pd(II) to
the triple bond in the intermediate A forms the intermediate B,
followed by an intramolecular 6-endo-dig carbocyclization to
afford the intermediate C. Then, the hydrolysis of intermediate
C leads to the intermediate D with concomitant regeneration
of the Pd(II) catalyst. The deprotonation of intermediate D in
the presence of sodium acetate as a basic salt generates
intermediate E. Finally, the Lossen rearrangement process
occurrs as reported in literature,14 furnishing the intermediate
F, which quickly performs decarboxylation and protonolysis to
afford the desired product 3.
In conclusion, we developed a palladium-catalyzed cascade
decarboxylative amination/6-endo-dig benzannulation of o-
alkynylarylketones with N-hydroxyamides, which provided an
efficient and convenient protocol for the synthesis of highly
functionalized 1-naphthylamines with a wide range of
structural diversity under mild reaction conditions, regardless
of their attached substituents. Through the palladium-catalyzed
cascade reactions, the 1-naphthylamine framework was
efficiently accessed, in which one C−C bond, one C−N, and
a new benzene ring were formed simultaneously in a single
operation with exclusive 6-endo-dig selectivity. The reaction
can be easily transformed and scaled up to the gram scale
without diminishing the product yield.
assess the possibility of key intermediates, aniline, phenyl
isocyanate, and benzamide were subjected to the standard
condition, respectively (Scheme 3a). Only a trace amount of
the desired product 3aa was produced (detected by TLC). 3-
Phenyl-1-naphthalenol 10 was then employed instead of o-
alkynyl aryl ketone 1a to investigate whether it was an
intermediate in the process, yet the desired product 3aa was
not detected by TLC (Scheme 3b). Furthermore, other
amides, such as N-(benzoyloxy)benzamide 11 and benzyl
hydroxycarbamate 12, also failed to get the corresponding
products under the standard conditions (Scheme 3c, 3d). In
addition, a deuterium labeling experiment with the addition of
deuterium oxide (0.3 mL) to the reaction system was carried
out, and the result indicated only the deuterated product 3aa-
d2 with 90% deuteration at the C-2 and C-4 position was
obtained in 90% yield (Scheme 3e). However, the deuterated
product was hardly obtained when the reaction was performed
in toluene-d8 for12 h (Scheme 3f), illustrating that the reaction
may proceed via a keto−enol tautomerization, dehydration,
and/or hydrolysis process.
ASSOCIATED CONTENT
■
sı
* Supporting Information
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/acs.orglett.0c01183.
General experimental procedure, characterization data of
the compounds (PDF)
Accession Codes
CCDC 1989392 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
via www.ccdc.cam.ac.uk/data_request/cif, or by emailing
data_request@ccdc.cam.ac.uk, or by contacting The Cam-
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
On the basis of the experimental results and literature
reports,8 a plausible decarboxylative amination/intramolecular
6-endo-dig benzannulation process was proposed, as depicted
D
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Org. Lett. XXXX, XXX, XXX−XXX

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Letter
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AUTHOR INFORMATION
Corresponding Authors
■
Xinwei He − Key Laboratory of Functional Molecular Solids,
Ministry of Education, Anhui Laboratory of Molecule-Based
Materials (State Key Laboratory Cultivation Base), College of
Chemistry and Materials Science, Anhui Normal University,
Wuhu 241000, P. R. China; orcid.org/0000-0002-1974-
2464; Email: xinweihe@mail.ahnu.edu.cn
Yongjia Shang − Key Laboratory of Functional Molecular
Solids, Ministry of Education, Anhui Laboratory of Molecule-
Based Materials (State Key Laboratory Cultivation Base),
College of Chemistry and Materials Science, Anhui Normal
University, Wuhu 241000, P. R. China; orcid.org/0000-
0001-9873-9150; Email: shyj@mail.ahnu.edu.cn
Ma, Z.; Kurti, L.; Falck, J. R. Science 2016, 353, 1144. (f) Choy, P. Y.;
̈
Chung, K. H.; Yang, Q.; So, C. M.; Sun, R. W.-Y.; Kwong, F. Y. Chem.
- Asian J. 2018, 13, 2465.
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Authors
Youpeng Zuo − Key Laboratory of Functional Molecular Solids,
Ministry of Education, Anhui Laboratory of Molecule-Based
Materials (State Key Laboratory Cultivation Base), College of
Chemistry and Materials Science, Anhui Normal University,
Wuhu 241000, P. R. China
Qiang Tang − Key Laboratory of Functional Molecular Solids,
Ministry of Education, Anhui Laboratory of Molecule-Based
Materials (State Key Laboratory Cultivation Base), College of
Chemistry and Materials Science, Anhui Normal University,
Wuhu 241000, P. R. China
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S.-F. J. Am. Chem. Soc. 2019, 141, 2535.
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Wangcheng Hu − Key Laboratory of Functional Molecular
Solids, Ministry of Education, Anhui Laboratory of Molecule-
Based Materials (State Key Laboratory Cultivation Base),
College of Chemistry and Materials Science, Anhui Normal
University, Wuhu 241000, P. R. China
Tongtong Zhou − Key Laboratory of Functional Molecular
Solids, Ministry of Education, Anhui Laboratory of Molecule-
Based Materials (State Key Laboratory Cultivation Base),
College of Chemistry and Materials Science, Anhui Normal
University, Wuhu 241000, P. R. China
(11) (a) Guo, B.; Zhou, Y.; Zhang, L.; Hua, R. J. Org. Chem. 2015,
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Complete contact information is available at:
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The work was partially supported by the National Natural
Science Foundation of China (No. 21772001) and the Anhui
Provincial Natural Science Foundation (No. 1808085MB41).
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