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Synthesis of Enaminones via Copper-Catalyzed Decarboxylative
Coupling Reaction under Redox-Neutral Conditions
Zhongzhi Zhu, Xiaodong Tang, Jianxiao Li, Xianwei Li, Wanqing Wu, Guohua Deng*, Huanfeng Jiang*
Published on 21 February 2017. Downloaded by University of Newcastle on 21/02/2017 18:40:24.

Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5 DOI: 10.1039/b000000x

ChemComm Accepted Manuscript

A novel copper-catalyzed C(sp3)-H oxidative functionalization
of aromatic oxime acetates with -oxocarboxylic acids was
reported. This process involved N-O/C-C bond cleavages and
C-C bond formations to furnish substituted enaminones
10 under redox-neutral conditions. The oxime acetates served as
both reactants and internal oxidants. Furthermore, this
transformation also features good functional group tolerance
and needs no ligands or additional bases.
Enaminones are key core units found in biologically active
15 molecules, 1a natural products,1b materials science1c and synthetic
pharmaceutical agents. They are also used in the synthesis of
heterocycles and pharmaceutical compounds. For example,
bioactive heterocycles (pyrroles,2a, 2b quinolines,2c, 2d
pyridaziniums,2e indoles2f, 2g, pyrazoles2h, 2l pyridines2m) and
20 drugs3(anticonvulsants3a, antibacterials 3b). Moreover, they were
also used as ligands for transition metal-catalyzed reactions.4
Therefore, the development of efficient transformations for the
preparation of enaminones from readily available starting
materials has attracted considerable attention. Over the past
25 decades, many methods have been developed for the synthesis of
enaminones, such as the direct condensation reaction of 1,3-
dicarbonyl compounds with amines,5 the aldol-type addition
reaction of carbonyl compounds with nitrile and the rings
opening reaction of heterocycles. There were also some good
30 work by polymerization approaches with alkynes, amines and
aldehydes9 or diaroyl chlorides.10 In spite of the successful
synthesis of enaminones, there are some limitations, including the
need of high functional substrates such 1,3-dicarbonyls or the use
cross-coupling of benzoyl radical and -carbon radical can lead to
the formation of carbon-carbon bond.
Oximes are fascinating and versatile building blocks in organic
synthesis due to their easy preparation, efficient reactivity and
50 harmless by-products. In addition, they were widely employed for
preparing the nitrogen-bearing heterocyclic compounds via SN2
reaction,15 radical cyclization.16 Recently, CH functionalization
of oxime derivatives with transition-metal catalyzed have
attracted more and more chemists attentions 17, especially oxime
55 derivatives used as radical reagents for the transition-metal-
catalyzed a-C(sp3)-H bond activation reactions14. Our group first
reported copper-catalyzed radical cross-coupling reaction of
oxime acetates with sodium sulfinates for the synthesis of sulfone
derivatives (Scheme 1a).14b Whereafter, Leis group developed
60 copper-catalyzed -phosphorylation of aryl ketone O-
acetyloximes for the formation of -ketophosphonates (Scheme
1b).14c Though the significant progress that has been achieved
along these lines, the obvious restrictive limitation is that the
product are usually hydrolysis to ketone because of the instability
65 of enamine group. Herein, we report the development of a
copper-catalyzed alkyl C(sp3)-H bond activation and
decarboxylative with -oxocarboxylic acids and directly afforded
enaminones as the stabilizing effect of intramolecular hydrogen
bonds.
(a) Our Previous work
OAc O
N
R3SO2Na
Cu(OAc) 2,100 oC
SO2R3 C-S formation
+ Ar
R1
Ar ref 16a
R1
Enamine hydrolysis

of excessive additives and/or ligands. Therefore, the preparation (b) Lei 's work

35 of enaminones from readily accessible materials with mild N

OAc O O O
R'
+ H P R' CuCl, 130 oC P C-P bond formation
conditions is one continuing challenge. Ar
R
R'
Ar
R' Enamine hydrolysis
ref 16b R
(c) This work
Carbon-carbon bond formation plays a central role in organic OAc O NH2 O
synthesis.11 As an important strategy, the selective radical/radical N
R + Ar' OH CuI, 90 oC C-C bond formation
Ar Ar Ar' Enamine retain
cross-coupling12 between a persistent radical and a transient 70
O R

40 radical have represented a powerful approach for achieving this
goal. Benzoyl radical may be considered as a persistent radical
which is easily produced from -oxocarboxylic acids.13 Based on
our and others continuous studies on oxime acetates14, it is
believed that enamide intermediate radicals or -carbon radical
45 species could be formed by the oxime esters. Thus, the selective
Scheme 1. The a-C(sp3)-H bond activation of oxime acetates.
In our initial studies, we took acetophenone oxime acetate (1a),
2-oxo-2-phenylacetic acid (2a) as the model substrates to
75 investigate different reaction conditions, and the results were
summarized in Table 1. To our delight, the desired product

This journal is The Royal Society of Chemistry [year] [journal], [year], [vol], 0000 | 1
 ChemComm Page 2 of 4
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DOI: 10.1039/C7CC00260B

enaminone 3aa was detected in 55% GC yield when using CuI as
the catalyst in CH3CN at 90 oC in a sealed tube for 6 h (entry 1).
Further copper salts screening suggested that copper(I) such as
CuCl, CuBr also catalyzed this reaction, but none of them were
5 found to be more efficient than CuI (entries 23). In contrast, the
copper(II) salts such as CuBr2, Cu(OAc)2, and Cu(OTf)2 did not
catalyze this conversion (entries 4-6). Subsequently, different
solvents such as DMSO, DMA, DMF, toluene and DCE were
also tested. DMF was revealed best to the reaction and gave 3aa
10 in 72% GC yield (entries 7-11). However, no significant effects
Published on 21 February 2017. Downloaded by University of Newcastle on 21/02/2017 18:40:24.
oxime acetates such as thiophene, furan, pyridine were
demonstrated compatible under our standard conditions,
40 rendering 3an, 3ao and 3ap in 73%, 61% and 52% yields,
respectively. 1-Acetylnaphthalene oxime acetate was a suitable
substrate for this reaction in 48% yield (3aq), In addition,
tetralone oxime acetate also afforded the desired product 3ar in
good yield.
45 Table 2. Substrate scope of various oxime acetates.a

were observed when the reactions were performed under O2 and

N2 atmosphere (entries 12-13). Moreover, considering the effect
of water on the reaction, molecular sieves (4) were added as an
additive increased the yield to 92% (entry 14). Thereafter,

ChemComm Accepted Manuscript

15 investigation of the temperature showed that 90 oC exhibited best
for this transformation (entries 15-16). Finally, no product was
obtained in the absence of copper salt (entry 17).
Table 1. Screening for optimal reaction conditions.a

Entry [Cu] Additive Solvent T (oC) Yield (%) b

1 CuI - CH3CN 90 55
2 CuCl - CH3CN 90 9
3 CuBr - CH3CN 90 11
4 CuBr2 - CH3CN 90 n.d.
5 Cu(OAc)2 - CH3CN 90 n.d.
6 Cu(OTf)2 - CH3CN 90 n.d.
7 CuI - DMSO 90 n.d. a
Reaction conditions: unless otherwise noted all reactions were
8 CuI - DMF 90 72 performed with 1 (0.3 mmol), 2a (0.36 mmol), CuI (10 mol %), 4 M.S.
9 CuI - toluene 90 n.d. 50 mg and dry DMF (2.0 mL) in a sealed tube for 6 h.
10 CuI - DCE 90 n.d. 50 Table 3. Substrate scope of various -oxocarboxylic acids.a
11 CuI - DMA 90 54
NOAc O NH2 O
12 c CuI - DMF 90 70 CuI, M.S.(4A)
O
CuI DMF 90 H
13 d - 72 +
R DMF, 90 oC
O
14 CuI e
M.S. DMF 90 92 (84) f R
1a 2 3
15 CuI e
M.S. DMF 80 66
16 CuI e
M.S. DMF 100 55 NH2 O NH2 O NH2 O

17 - e
M.S. DMF 90 n.d.
a F
20 Reaction conditions: unless otherwise noted, all reactions were
3as, 85% 3at, 84% 3au, 67%
performed with 1a (0.3 mmol), 2a (0.36 mmol), [Cu] (10 mol %),
additive (0.3 mmol) and solvent (2.0 mL) in a sealed tube for 6 h. b NH2 O NH2 O NH2 O
Yields analyzed by GC/MS based on 1a with dodecane as internal
standard. n.d. = not detected. c Under N2 atmosphere. d Under O2
Cl
25 atmosphere. f M.S. = molecular sieves (4 ), 50 mg was used. f Isolated Br O
3av, 76% 3aw, 71% 3ax, 61%
yield.
NH2 O NH2 O NH2 O
Based on the optimization study, we first investigated the O S
scope of oxime acetates and the results are summarized in Table
NO2
2. Generally, this reaction proceeded smoothly and gave the 3az, 65%
3ay, 64% 3ba, 61%
30 desired products 3 in moderate to good yields. A series of para- NH2 O
NH2 O
substituted acetophenone oxime acetate, including some with
electron-donating groups (Me, Et, OMe) and some with electron-
withdrawing groups (F, Cl, Br, CF3) were converted into the 3bb, 54% 3bc, 0%
corresponding enaminones in good yields (3aa3ah). a
Reaction conditions: unless otherwise noted all reactions were
35 Furthermore, ortho, meta-substituted and poly-substituted performed with 1a (0.3 mmol), 2 (0.36 mmol), CuI (10 mol %), 4 A M.S.
acetophenone oxime atceates were able to give the desired (50 mg) and dry DMF (2.0 mL) in a sealed tube for 6 h. Isolated yields.
products in moderate to good yields (3ai-3am). The heteroarene 55 Next, the scope of -oxocarboxylic acids was examined in this
reaction (Table 3). In general, a variety of -oxocarboxylic acids

2 | Journal Name, [year], [vol], 0000 This journal is The Royal Society of Chemistry [year]
 Page 3 of 4
with different substituents on the aromatic ring were found to be
tolerable in this process. For example, -oxocarboxylic acids with
electron-donating substituents (Me, MeO) afforded the desired
enaminones in good yields (3as, 3at, 3ax). While -
5 oxocarboxylic acid derivatives bearing electron-withdrawing
substituents (F, Cl, Br, NO2) provided the desired products in
moderate yields ranging from 64% to 76% (3au-3aw, 3ay).
Satisfactorily, furoylformic acid and 2-thienylglyoxylic acid
offered the desired products in 65% and 61% yields, respectively.
10 Gratifyingly, naphthyl oxocarboxylic acid also efficiently reacted
Published on 21 February 2017. Downloaded by University of Newcastle on 21/02/2017 18:40:24.
with 2a, giving the product 3bb in 54% yield. Unfortunately,
aliphatic oxocarboxylic acid failed to undergo desired reaction
(3bc).
O O
4
99%
H
NH2 O H R
N N N
NOAc
2a, 1.8g R NH2
standard condition
3aa, 1.83g
1a, 1.77g
82% 6a, R = H, 84%
6b, R = Ph, 90%
NH2OH
O N
5, 90%
15
Scheme 2. Large-scale synthesis of 3aa and its application
To demonstrate the practical utility of this novel method, the
reaction of 1a and 2a was performed at the 10 mmol scale. The
20 desired 3aa was formed in 82% yield (Scheme 2). Hydrolysis of
3aa with dilute sulphuric acid is smoothly proceeded, almost
quantitatively providing the desired product 4. The
hydroxylamine cyclization of 3aa with hydroxylamine
hydrochloride also gave isoxazole 5 with high yield. Moreover,
25 3aa reacted smoothly with hydrazine hydrate or phenylhydrazine,
and gave the pyrrole products 6a and 6b with good yields.
To gain more insight into the mechanism of the process, we
conducted two control experiments illustrated in Scheme 3. When
2.0 equiv of TEMPO or butylated hydroxytoluene (BHT) was
30 added, the reaction was completely shut off. This result indicated
that a radical process may involve in this transformation.
Scheme 3. Investigation into the reaction mechanism.
35
On the basis of these experiments and previous reports,13, 14 a
plausible reaction mechanism involving radical/radical cross-
coupling was proposed (Scheme 4). Firstly, reductive acylation
of acetophenone oxime acetate 1 by CuI in a single-electron-
40 transfer reaction smoothly transferred to iminium radical I, which
quickly isomerized to -carbon radical II. On the other hand, CuII
This journal is The Royal Society of Chemistry [year]
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DOI: 10.1039/C7CC00260B
abstracted a single electron from carboxylate to produce the
carboxyl radical, and the latter was quickly decarboxylated to
produce acyl radical III. Subsequently, selective cross-coupling
45 of the radical species II and III constructed a new C-C bond to
afford imine IV, which rapidly isomerized to the desired product
3.
ChemComm Accepted Manuscript
Scheme 4. Possible reaction mechanism.
50 In summary, we have developed an novel copper-catalyzed
C(sp3)-H oxidative functionalization of oxime acetates with -
oxocarboxylic acids. Furthermore, the reaction was accomplished
6 through N-O/C-C bond cleavages and C-C bond formations to
afford substituted enaminones. Moreover, the use of simple
55 starting materials, no need of bases or ligands, no toxic
byproducts make this method practical and particularly attractive.
We are grateful to the National Natural Science Foundation of
China (21172076 and 21420102003) and the Fundamental
60 Research Funds for the Central Universities (2015ZY001).
Notes and references
Key Laboratory of Functional Molecular Engineering of Guangdong
Province, School of Chemistry and Chemical Engineering, South China
University of Technology, Guangzhou 510640, China. Fax: +86 20-
65 87112906; Tel: +86 20-87112906; E-mail: jianghf@scut.edu.cn;
ghdeng@scut.edu.cn.
Electronic Supplementary Information (ESI) available: Experimental
section, characterization of all compounds, copies of 1H and 13C NMR
spectra for selected compounds. See DOI: 10.1039/b000000x/
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4 | Journal Name, [year], [vol], 0000 This journal is The Royal Society of Chemistry [year]