Cu-catalyzed oxygenation of alkene-tethered amides with O2: Via unactivated CC bond cleavage: A direct approach to cyclic imides

Article abstract of DOI:10.1039/c9sc03175h

The transformations of unactivated alkenes through CC bond double cleavage are always attractive but very challenging. We report herein a chemoselective approach to valuable cyclic imides by a novel Cu-catalyzed geminal amino-oxygenation of unactivated CC bonds. O₂ was successfully employed as the oxidant as well as the O-source and was incorporated into alkenyl amides via CC bond cleavage for the efficient preparation of succinimide or glutarimide derivatives. Moreover, the present strategy under simple conditions can be used in the late-stage modification of biologically active compounds and the synthesis of pharmaceuticals, which demonstrated the potential application.

Full text of DOI:10.1039/c9sc03175h

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DOI: 10.1039/C9SC03175H
COMMUNICATION
Cu-catalyzed Oxygenation of Alkene-tethered Amides with O2 via
Unactivated C=C Bond Cleavage: A Direct Approach to Cyclic
Imides
Received 00th January 20xx,
Accepted 00th January 20xx
Junhua Li,a Jialiang Wei,a Bencong Zhu,a Teng Wangb and Ning Jiao*ac
DOI: 10.1039/x0xx00000x
The transformations of unactivated alkenes through C=C bond
double cleavage are always attractive but very challenging. We
report herein a chemoselective approach to valuable cyclic imides
by a novel Cu-catalyzed geminal amino-oxygenation on the
unactivated C=C bonds. O2 was successfully employed as the
oxidant as well as the O-source, and was incorporated into alkenyl
amides via C=C bond cleavage for the efficient preparation of
succinimide or glutarimide derivatives. Moreover, the present
strategy under simple conditions can be used in the late-stage
modification of biologically active compounds and the synthesis of
pharmaceuticals, which demonstrated the potential application.
Figure 1. Some pharmaceuticals with succinimide and glutarimide moieties.
challenging due to tedious transformations that are required
for the preparation of anhydride precursors.
It is instructive that the difunctionalization of alkenes is such
a versatile transformation for the assembly of two individual
functional groups across C=C double bonds.11 Alkene-tethered
amides, which serve as the substrates for intramolecular
amidation of unactivated alkenes initiated by the photo-
induced amidyl radical formation or metal-mediated
amidocyclization, have emerged as the ideal precursor of γ-
lactams in recent years with well established transformations12
(Scheme 1 a1).
Recently, O2 or air has been regarded as an ideal oxidant
because of its inexpensive, environmentally benign and high
atom economy characteristics, which attracts academic and
industrial attentions.13 The oxygenations of olefins enable
efficient protocols for the construction of epoxides,14 diols,15
and ketones16 with/without C=C double bond cleavage.17
Given what we discovered in our previous studies on the
oxygen mediated C=C bond cleavage,18 we proposed that the
geminal olefin amino-oxygenation of pent-4-enamides via
chemoselective C=C double bond cleavage, would be highly
promising to produce succinimides in the presence of oxygen
(Scheme 1b). To date, the aerobic oxidation of enamides has
only been documented in the Pd(II)-catayzed intramolecular
The 5- and 6-membered cyclic imide moiety is frequently
present as the key subunit in substantial pharmaceuticals and
bioactive compounds1 (Figure 1). For instance, the 5-
membered cyclic imides (succinimides)
commonly used to treat petit malepilepsy,2 while the 6-
membered cyclic imides (glutarimides) iv , and vi could be
used as antineoplastic and
sedative-hypnotics,3
i, ii and iii are
,
v
immunomodulatory drugs.4 Interestingly, the penitential
thalidomide vi has returned to the market as the treatment of
cancer under the brand name Immunoprin,5 since the
conviction of the culprit of phocomelia in 1960s.6 The
evolution of synthetic methods for cyclic imides is
continuously driven forward by their importance in medicinal
chemistry. Typical methods for the synthesis of simple imides
include the ammonolysis of anhydrides under high
temperature,7 the oxidation of lactams with strong or special
oxidants,8 and the reduction of unsaturated imides such as
maleimide,9 or metal-catalyzed carbonylation of various
precursors.10 However, the approaches to polysubstituted
cyclic imides remains
aza-Wacker-type cyclization.19 Recently,
aminooxygenation 4
a
significant
‑
pentenylsulfonamides was reported by
Chemler and coworkers (Scheme 1 a2),20 in which the C=C
bond cleavage were successfully achieved but by two steps.
The DABCO was required as a base with the formation of γ-
lactam products. To the best of our knowledge, the
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Table 2. Substrate scope for the synthesis of succinimidesa
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chemoselective cleavage of C=C double bonds in alkene-
tethered amides for cyclic imides synthesis has not been
accomplished yet.
DOI: 10.1039/C9SC03175H
Scheme 1. The strategies for the oxygenation of unactivated alkenyl amides.
Our investigation commenced with N-methoxy alkenyl
amide 1a. After a lot of experiments, we were surprised to find
that the containing unactivated C=C double bond could be
cleaved with the incorporation of one oxygen atom by O2.
Encouraged by the copper catalyzed olefin amino-oxygenation
which delivered 2a in 47% yield (Table 1, entry 1), a variety of
conditions were screened (see SI). The control experiments
demonstrated that the reaction could not work in the absence
of copper catalyst, or oxygen atmosphere (Table 1, entries 2-3).
Besides, different copper catalyst, solvents, additives and
ligands were also screened (Table 1, entries 5-10). The yields
were sharply decreased when bases or acids were used as
additives. Finally, we found that the reaction with copper
acetate as the catalyst, bathocuproine (Ligand II) as ligand in
toluene executed the unactivated C=C double bond geminal
amino-oxygenation reaction well and produced the desired
succinimide product 2a in excellent efficiency (83% isolated
yield, Table 1, entry 10).
a Reaction conditions: see entry 10, Table 1. Isolated yields. b Reaction for 48
hours.
Subsequently, a good number of pent-4-enamides were
smoothly converted to succinimides in moderate to good
yields (Table 2). Several N-alkoxy protecting groups were well
tolerated (up to 84%, 2a
groups were inferior (2d
-
,
2c) while substrates bearing bulky
2e). When hydrogen atom (2f) or
benzyl group (2g) attached to the amide nitrogen, the reaction
did not work. The reason is that the alkyl−metal intermediates
formation might be favored in the assistance of alkoxy
12e
protecting group.12d,
α-Geminal substituted substrates
worked well in this transformation (Table 2, 2h-2o), producing
polysubstituted and spiro-succinimides in moderate to good
yields. It is noteworthy that the reaction could contain one of
the identical allyl groups specifically to give the allylic imide in
44% yield (2o). The mono methyl or benzyl substituted
enamides were also tolerated, and the desired products could
be obtained in fair yields (2p and 2q). To our delight, the
vinylcyclohexane derived enamide underwent the process
smoothly to afford the corresponding imide 2s. The 2-
vinylbenzamide was also compatible to give the synthetic
important phathlimide 2t albeit the efficiency is a little bit low,
because the conjugated alkenes would undergo un-wanted
oxidation. Unfortunately, the alkene-tethered amide without
alkylation on the backbone did not work. Notably, the
Table 1. Screening of reaction conditionsa
glutarimide derivatives 4a-4d were also obtained in moderate
yields with hex-5-enamides (Table 3).
To demonstrate the synthetic value of our strategy, several
late-stage modifications of biologically active compounds were
carried out under the standard conditions (Scheme 2).
Table 3. Substrate scope for the synthesis of glutarimidesa
a
Reaction conditions: 1a (0.2 mmol), catalyst (0.02 mmol), ligand (0.024
mmol) and additive (1.0 equiv.) were stirred in solvent (2.0 mL) at 80 ℃
under O2. b Determined by H NMR analysis using 1,1,2,2-tetrachloroethane
1
c
as internal standard. The numbers in parentheses are isolated yields.
Under argon atmosphere. Not detected. e This reaction was carried out
d
under air.
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cyclization process. Then, to investigate the intermediacy of
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aldehyde in the C=C bond cleavage, 2-DpOyrI:ro10li.1d0i3n9o/nCe9SC10931w75aHs
employed under standard conditions. The formation of 2r with
some unconsumed raw materials compared with the result in
Table 2 indicate that the aldehyde might be involved in this
transformation (Scheme 4b). In addition, the isotopic labeling
studies under 18O2 delivered the labeled succinimide [18O]-2a
in
a Reaction conditions: see entry 10, Table 1. Isolated yields.
Scheme 4. Mechanistic studies.
Scheme 2. Application in the synthesis of drug analogues.
Scheme 3. Synthesis of succinimide-containing medicines.
100
80
60
40
20
0
Naproxen, approved by the USA Food and Drug Administration
(FDA) for anti-inflammation, antipyretics and analgesics, could
deliver succinimide
6
in 78% yield via analogue
5
under the
was
standard conditions (Scheme 2). The structure of
6
confirmed by X-ray single crystal structural analysis.
Additionally, the derivatives of best-seller drugs Ibuprofen and
Flurbriprofen could also undergo the present transformation
0
200
400
600
800
1000
Time (min)
Figure 2. Kinetic profile of this C=C bond oxygenation reaction.
to afford the desired product
8 in 60% yield and 10 in 75%
80% yield (67% 18O) due to the exchange with H2O (see SI),
which supports our expectation. We also studied the reaction
kinetic profile, which showed the initial increase and later
consumption of aldehyde intermediate along with the
formation of succinimide (Figure 2). This result was in
accordance with our aforementioned observation. The
tentative studies on trapping intermediates were also carried
out by EPR (see SI).
yield respectively. These results provide efficient approaches
to drug analogues for future medicinal chemistry studies.
Furthermore, our strategy can be applied to the synthesis of
two pharmaceutical compounds Ethosuximide
i
and
Methsuximide ii (Figure 1). As shown in Scheme 3, the
amidocyclization of 11 gave N-benzyloxy succinimide 12 in 69%
yield under the standard conditions, followed by the removal
of the N-benzyloxy group by hydrogenation and treatment of
2-bromoacetophenone and triethylamine to furnish21 the
Based on previous reported12e, 20 and our own mechanistic
studies, a plausible mechanism is shown in Scheme 5. We
proposed that copper(I) is oxidized to copper(II) by O2 in the
initial step. Then, copper(II)-catalyzed alkene cis-
amidocupration affordes an unstable organocopper(II)
Ethosuximide in high yield
(13, 83%), which possess
antiepileptic effect. This method avoids the use of highly toxic
hydrocyanic acid in industrial production. Similarly, the
Methsuximide 17 could also be obtained from the succinimide
15 in good overall yield.
In order to probe the mechanism, some control experiments
were designed and investigated (Scheme 4). Firstly, the
reaction was conducted in the presence of TEMPO as a radical
scavenger, and the difunctionalization product 18 could be
obtained in 87% yield, with the formation of 2a in only 10%
yield (Scheme 4a). This result indicates that an alkyl radical
intermediate was produced after the intramolecular amido-
intermediate
TEMPO (Scheme 4a), is subsequently generated by the C−Cu
homolysis of intermidiate B 22
The mechanism is not
B. Primary radical C which could be trapped by
.
completely clear yet. Alternatively, the lack of detection of the
amidyl radical by EPR analysis (see SI) could not fully disprove
its presence under the reaction conditions. The primary radical
C
may also be generated by the addition of amidyl radical to
the double bond. Then, the radical species is trapped by
C
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molecular oxygen and produces the superoxide radical
the intramolecular 1,3-hydrogen migration occurs to form the
intermediate , followed by the O−O homolysis to give the
aldehyde and hydroxyl radical which is unstable and easily
reduced in situ to give hydroxide anion. The intermediate
D. Then,
Notes and references
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DOI: 10.1039/C9SC03175H
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the alkene-tethered amides via
a
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cyclization/C=C bond cleavage processes that revealed an
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Conflicts of interest
The authors declare no competing financial interest.
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Financial support from the National Basic Research Program of
China (973 Program) (No. 2015CB856600), the National
Natural Science Foundation of China (21632001, 21772002,
81821004), the Drug Innovation Major Project (2018ZX09711-
001), and the Open Research Fund of Shanghai Key Laboratory
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appreciated.. We thank Xinyi Zhao in our group for
reproducing the results of 2n and 4b
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