Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes

Article abstract of DOI:10.1007/s13738-021-02254-4

We started our study by preparation two ketoximes. Later, there were studies to reveal these ketoximes' effects in the electrophilic amination reaction with organocadmium reagents. Primarily, it was observed that arylcadmium iodides could not be reacted with ketoximes at room temperature in the absence of a catalyst. CuCN was a suitable catalyst for this electrophilic amination reaction of arylcadmium iodides and allowed the preparation of functionalized aniline derivatives in good yields under mild reaction conditions. We obtained the results indicated that the yield of primary arylamines was strongly dependent on the steric and electronic effects of organocadmium reagent and amination agent. In the case of both amination reagents, meta-substituted arylamines were obtained in higher yields than para-substituted arylamines. We observed that acetone O-(4-chlorophenylsulfonyl)oxime, 1, as an aminating agent, was more successful than acetone O-(2-Naphthylsulfonyl)oxime, 2, in the synthesis of functionalized arylamines by electrophilic amination of corresponding aryl cadmium iodides. In this method, there is no cadmium release to the environment.

Full text of DOI:10.1007/s13738-021-02254-4

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-021-02254-4
ORIGINAL PAPER
Room‑temperature copper‑catalyzed electrophilic amination
of arylcadmium iodides with ketoximes
Adem Korkmaz1
Received: 24 February 2021 / Accepted: 16 April 2021
© Iranian Chemical Society 2021
Abstract
We started our study by preparation two ketoximes. Later, there were studies to reveal these ketoximes’ efects in the electro-
philic amination reaction with organocadmium reagents. Primarily, it was observed that arylcadmium iodides could not be
reacted with ketoximes at room temperature in the absence of a catalyst. CuCN was a suitable catalyst for this electrophilic
amination reaction of arylcadmium iodides and allowed the preparation of functionalized aniline derivatives in good yields
under mild reaction conditions. We obtained the results indicated that the yield of primary arylamines was strongly dependent
on the steric and electronic efects of organocadmium reagent and amination agent. In the case of both amination reagents,
meta-substituted arylamines were obtained in higher yields than para-substituted arylamines. We observed that acetone
O-(4-chlorophenylsulfonyl)oxime, 1, as an aminating agent, was more successful than acetone O-(2-Naphthylsulfonyl)oxime,
2, in the synthesis of functionalized arylamines by electrophilic amination of corresponding aryl cadmium iodides. In this
method, there is no cadmium release to the environment.
Keywords Electrophilic amination · Organocadmium reagents · Amines · Ketoximes · Catalysis · Organometallic
Introduction
equiv.) as an aminating agent in the presence of 5 mol%
FeSO4 as a catalyst in MeCN/H2O at room temperature
after a 16 h reaction. Amination of electron-poor arenes
by this method was performed in HFIP (hexafuoroisopro-
panol), in the presence of 1 mol% FeSO4 at 60 °C [15]. Jiao
and co-workers used 4-NO2-PhCOONH3+ −OTf as an aryl
C−H amination agent [16]. The reaction was carried out
successfully in the presence of FeBr2 as catalyst (5 mol%)
and AgNTf2 as an additive (10 mol%). Cu(OTf)2/1,10-phen-
anthroline-catalyzed amination of arenes in the presence of
CsOH.H2O in HFIP using hydroxylamine-O-sulfonic acid
(H2N-OSO3H) as an electrophilic nitrogen source resulted
in good yields of primary arylamines [17].
Since amines are used as starting materials both in organic
synthesis and in the preparation of important compounds
and materials in the industry [1–8]. New studies are con-
stantly being carried out to develop more applicable and
highly efcient methods for their synthesis [9].
Therefore, the development of procedures allowing the
synthesis of arylamines under mild reaction conditions
and in high yields is of signifcant importance. Although
nearly all the methods in the literature let obtaining primary
arylamines in good yields, most of them have signifcant
drawbacks such as the requirement of a high temperature,
long reaction condition, high pressure, expensive or specifc
catalysts, and ligands[10–13].
To date, many procedures have been published for the
electrophilic amination of organomagnesium, -zinc and
-copper reagents with various electrophilic amination
agents [18]. Recently, Knochel’s group showed that cobalt-
catalyzed electrophilic amination of arylzinc pivalates with
several anthranil derivatives allowed the formation of cor-
responding amino-aldehydes and amino-ketones in good
to high yields at room temperature after 16 h [19]. Kürti’s
group used N–H oxaziridines (1.2 equiv.) for the transfer of
primary amino group (–NH2) to arylmagnesium bromides.
They conducted this electrophilic amination reaction in
Morondi and co-workers described an iron-catalyzed
aromatic C–H amination procedure for the preparation of
primary anilines [14]. They managed to obtain various func-
tionalized primary anilines, using MsO-NH3+ −OTf (1.5
* Adem Korkmaz
a.korkmaz@alparslan.edu.tr
1
Department of Occupational Health and Safety, Faculty
of Health Sciences, Muş Alparslan University, Muş, Turkey
Vol.:(0123456789)
1 3

Journal of the Iranian Chemical Society
toluene/THF mixture at 45 or 78 °C. The reactions were
completed in 16 h and arylamines were obtained in 16–89%
yields [20]. They used N–H oxaziridines for the electrophilic
amination of functionalized arylcuprates which prepared by
transmetallation of arylmagnesium, -zinc or -lithium rea-
gents with CuCN.2LiCl or CuCl.2LiCl at 78 °C [21].
Organocadmium reagents have been mostly used for the
synthesis of ketones from active substrates such as acid
halides or acid anhydrides. In addition, they have been
employed as alkylation reagents in the regioselective alkyla-
tion of quinines [22, 23]. But they have a high functional
group tolerance and if can be increased their reactivity
they can be used for the synthesis of functionalized organic
compounds.
temperature. To this mixture, CuCN (0.0089 g, 0.01 mmol),
and a solution of 1 or 2 (0.247 g or 0.263 g, 1 mmol) in dry
THF (2 mL) were added. The reaction mixture was stirred
at room temperature for 30 min and then worked up by the
addition of conc. HCl with stirring at room temperature for
24 h. The aqueous phase was washed with diethyl ether,
made basic with conc. NaOH (Cd(OH)2 precipitated as a
white solid) and the free amine was extracted with diethyl
ether (3×50 ml). The organic layer was dried over Na2SO4,
and the solvent was evaporated and the crude product was
converted to its N-benzoyl derivative by reaction with ben-
zoyl chloride in the presence of NaOH. The product was
recrystallized from ethanol–water (4:1). Benzamide deriva-
tives were identifed from their melting points 1H NMR and
13C NMR analysis.
Up to now, the Daşkapan group was developed successful
procedures for electrophilic amination of organomagnesium,
organozinc, and organocopper reagents [24–29]. The studies
in the literature about electrophilic amination of organocad-
mium reagents were published by our group [30, 34].
General procedure for the preparation of acetone
O‑(4‑Chlorophenylsulfonyl)oxime (1) and acetone
O‑(2‑Naphthylsulfonyl)oxime (2)
Acetone O-(4-Chlorophenylsulfonyl)oxime (1) and acetone
O-(2-Naphthylsulfonyl)oxime (2) were prepared accord-
ing to the method made by Korkmaz [34]. Acetonoxime
(13.70 mmol), DMF (4 mL), and triethylamine (1.9 mL)
were placed into 100-mL fask. This fask was immersed
into the ice bath and set up on a magnetic stirrer. Then,
4-chlorophenylsulfonyl chloride (13.70 mmol) was atten-
tively added piece by piece keeping stirring in 5–10 min.
The resulted reaction mixture stirred for 1 h, keeping in ice
bath. Then white solid formed by gently diluting the reaction
mixture by adding 50 mL of ice water. This crude product
was fltered of under vacua and dried in a desiccator. The
dry white solid was crystallized from hexane-benzene (5: 1)
mixture (1.962 g, 58%, mp 89–92 °C); 1H NMR spectrum
(CDCl3, ppm): 7.91–7.89 (d, 2H, Ar–C-H), 7.51–7.49 (d,
2H, Ar–C-H), 1.98 (s, 3H, CH3), 1.92 (s, 3H, CH3). 13C
NMR spectrum (CDCl3 olacak) δ(ppm): 165.36 (R1R2C=N),
140.46, 134.33, 130.22, 129.24 (Ar–C), 21.62, 16.96 (R–C).
Aceton O-(2-naphthylsulphonyl)oxime (2) was syn-
thesized following the same procedure (2.161 g, 60%, mp
92–95 °C); 1H NMR spectrum (CDCl3, ppm): 8.56 (s, 1H,
naphthyl-H), 7.93–7.90 (m, 4H, naphthyl -H), 7.68–7.59 (m,
Experimental section
General
All reactions involving arylcadmium iodide reagents were
performed in fame-dried glassware with standard syringe/
cannula techniques under an atmosphere of dry, oxygen-free
argon [31]. Melting points were determined on a Gallen-
camp capillary melting point. NMR spectra were recorded
on a Bruker DRX-400 high-performance digital FT-NMR
spectrometer. All chemical shifts were given in ppm down-
feld from tetramethylsilane (TMS).
THF was freshly distilled from the solution of
sodium–benzophenone under dry argon and kept over
molecular sieves (4 Å 4–8 mesh) and under argon atmos-
phere. Copper (I) cyanide was purifed prior to use and kept
under a dry argon atmosphere [32].
Organomagnesium bromides were prepared in THF by
conventional standard methods and their concentrations
were determined by the method of Watson and Eastham
[33]. Aryl bromides (Sigma-Aldrich) were in high purities
and used without any further purifcation.
2H, naphthyl -H), 1.98 (s, 3H, CH3), 1.89 (s, 3H, CH3). 13
C
NMR spectrum (CDCl3, ppm): 165.10 (R1R2C=N), 135.35,
132,80, 131.93, 130.70, 129.44, 129.30, 129.13, 127.93,
127.58, 123.32 (naphthyl-C), 21.64, 16.95 (R–C).
General procedure for CuCN‑Catalyzed electrophilic
amination of arylcadmium iodides with ketoximes
A solution of CdI2 (0.7324 g, 2 mmol) in anhydrous THF
(5 mL) was cooled to 10 °C under argon atmosphere and
2 mmol of arylmagnesium bromide in THF was added drop-
wise via syringe. The reaction mixture was stirred for an
additional 10 min, the cooling bath was removed, and the
resulting white suspension was allowed to warm to room
Results and discussion
In this manuscript, the results of our works on the reac-
tion of arylcadmium iodides with ketoximes in the pres-
ence of CuCN as a catalyst at room temperature are given.
1 3

Journal of the Iranian Chemical Society
According to our knowledge, these results will be the frst
data about electrophilic amination of arylcadmium iodides
with ketoximes.
Firstly, we reacted phenyl cadmium iodide with ketoxime
under catalyst-free conditions and we observed that the reac-
tion failed (Table 1, entries 1 and 2). Then we decided to
perform the reaction in the presence of a catalyst. For this
reason, we used 2.5–10 mol% CuCN as a catalyst and con-
tinued the reactions for 30 min. We observed that 5 mol%
of CuCN needed for the best arylamine yield. Chancing the
reaction time as 15 min or 60 min led to a decrease in the
yield (entry 7 and 8).
We used two novel ketoximes, acetone O-(4-chlorophe-
nylsulfonyl)oxime, 1, and acetone O-(2-Naphthylsulfonyl)
oxime, 2, as amination reagents. We prepared and purifed
these compounds according to the methods described in the
literature [35]. Arylcadmium iodides were prepared by trans-
metallation of the corresponding arylmagnesium bromides
with CdI2 in THF and controlled by Gilman’s color test [36].
Amination reaction was performed by cannulation of THF
solution of 1 or 2 into organocadmium reagent.
After determination of optimal reaction conditions using
amination reaction of phenylcadmium iodide as a model
reaction, we prepared various functionalized arylcadmium
reagents and reacted them with 1 under these reaction condi-
tions to show the scope of the method. As is seen in Table 1,
when aryl ring has a good electron-donating group, electro-
philic amination reaction resulted in high yield (entry 11)
but in the presence of strong electron-withdrawing group
lower yield of amine was obtained (entry 15). The results
obtained from reaction of functionalized arylcadmium
reagents showed that arylcadmium reagent gave a selec-
tive reaction with 1. For example, in the presence of an
electron-withdrawing substituent, meta-substituted aniline
was obtained in higher yield compared to para-substituted
Arylamines as the fnal products were removed from the
reaction mixture as their benzamide derivatives and these
known compounds were identifed from their melting points,
1H NMR, and 13C NMR analysis [37–42]. Cadmium was
removed from the reaction mixture as its white-colored salt
(Cd(OH)2) during the reaction mixture’s basifcation of
after hydrolysis with conc. HCl. Thereby cadmium was not
thrown as waste to the environment.
Since we aimed to develop an easy applicable procedure
for the electrophilic amination of arylcadmium iodides with
ketoximes, we conducted our works at room temperature.
Table 1 CuCN-catalyzed electrophilic amination of ArCdI with 1
Entry
Ar
CuCN (%)
Time (min.)
Yieldb (%)
1
2
3
4
5
6
7
8
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
4-ClC6H4
3-ClC6H4
4-CH3SC6H4
3,5-Cl2C6H3
4-MeOC6H4
3-MeOC6H4
4-FC6H4
4-CH3C6H4
4-Cl-2-MeC6H3
3,4,5-(MeO)3C6H2
0
0
7.5
5
10
2.5
5
5
5
5
5
5
5
5
5
5
5
5
30
180
30
30
30
30
15
60
30
30
30
30
30
30
30
30
30
30
–
–
50
73
41
65
61
55
58
70
73
48
59
85
64
60
64
51
9
10
11
12
13
14
15
16
17
18
aArCdI/1=2
1
bYield of amines was isolated as their N-benzoyl derivatives, and these known compounds were identifed from their melting point, H NMR,
and 13C NMR analysis [38–42]
1 3

Journal of the Iranian Chemical Society
aniline (entry 9 and 10). Similar results were obtained from
the reaction of the electron-donating group substituted
arylcadmium reagents (entry 13 and 14). While two elec-
tron-withdrawing group substituted arylcadmium gave the
corresponding amine in low yield (entry 12), electrophilic
amination reaction of one electron-withdrawing and one
electron-donating group substituted arylcadmium reagent
with 1 resulted in a good yield (entry 17).
and copper-catalyzed binding of organozinc reagents, and
explanations have been made considering these mechanisms
[43]. Arylcadmium iodides react with CuCN catalyst to form
catalytic amount of arylcyanocuprate, which is the real cata-
lyst. ArCuCN−, as a nucleophile, attacks on the electrophilic
nitrogen of ketoxime to form a Cu-III complex (Scheme 2,
a, oxidative addition).
The rate-determining step can prefer oxidative addition or
the reductive elimination step in the mechanism depending
on the reaction conditions, the nucleophile structure, and the
electrophile. Furthermore, both the electronic efects and
steric efects of these structures are efective in selecting
the rate-determining step [44, 45]. In the case of the amina-
tion of diarylcadmium containing a functional group, it is
not possible to give a precise sequence of activities. Steric
hindrance and electronegativity can be evaluated where they
are performed under the same reaction conditions. Thus, for
the arylcadmium iodide reagents having the same functional
group at diferent positions, the rate-determining step can
be estimated as the oxidative addition step or the reductive
elimination step thanks to the amine yields obtained.
It seems that this step occurs more easily when 1 is used
as an electrophilic amination agent for the aryl C-N bond for-
mation employing arylcadmium iodides as an organometallic
Unfortunately, acetone O-(2-Naphthylsulfonyl)oxime,
2, as an electrophilic nitrogen source, has not been as suc-
cessful as 1 in the electrophilic amination of aryl cadmium
reagents. Besides, in the presence of electron-withdrawing
group, there was not observed any meta-para selectivity
(Table 2, entries 8 and 9), in the case of electron-donating
substituent a low selectivity in favor of meta-position was
observed (Entries 12 and 13). According to these results,
the use of 1 for the formation of aryl C-N bond employing
arylcadmium iodides as the organometallic reagent is more
suitable than 2 (Scheme 1).
Scheme 2 shows the proposed mechanism for CuCN-
catalyzed electrophilic amination of arylcadmium iodides
with ketoximes. A mechanism for the CuCN-catalyzed elec-
trophilic amination of arylcadmium iodides has been pro-
posed using the literature data of organo-copper compounds
Table 2 CuCN-catalyzed electrophilic amination of ArCdI with 2
Entry
Ar
CuCN (%)
Time (min.)
Yieldb (%)
1
2
3
4
5
6
7
8
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
4-ClC6H4
3-ClC6H4
4-CH3SC6H4
3,5-Cl2C6H3
4-MeOC6H4
3-MeOC6H4
4-FC6H4
4-CH3C6H4
4-Cl-2-MeC6H3
3,4,5-(MeO)3C6H2
10
7.5
5
30
30
30
30
30
15
60
30
30
30
30
30
30
30
30
30
30
33
32
49
61
34
56
42
52
56
55
52
39
50
63
52
53
22
2.5
1.25
2.5
2.5
2.5
2.5
2.5
2.5
2.5
2.5
2.5
2.5
2.5
2.5
9
10
11
12
13
14
15
16
17
aArCdI/2=2
1
bYield of amines was isolated as their N-benzoyl derivatives, and these known compounds were identifed from their melting point, H NMR,
and 13C NMR analysis[38–42]
1 3

Journal of the Iranian Chemical Society
O
Cl
S Cl
O
O
CH3
CH3
Cl
S O N
O
DMF, Et3N, 1h, -10 oC
1
CH3
HO N
O
S Cl
O
CH3
O
CH3
CH3
S O N
O
DMF, Et3N, 1h, -10 oC
2
Scheme 1 Preparation of ketoximes
reagent. Because naphthylsulfonyiloxy group is bulkier than
4-chlorophenylsulfonyloxy group, and this leads to the need
less energy for the formation of Cu-III complex during the
reaction of 1 with arylcadmiums, compared to the forma-
tion by reaction of 2. meta-selectivity is interpreted as: the
meta-structure is more rounded than para-structure and thus
facilitates reductive elimination (Scheme 2, b) by creating a
steric efect in the Cu-III complex. The lack of a signifcant
selectivity in the amination reaction of 2 is due to the fact
that the bulky naphthylsulfonyloxy group facilitates reduc-
tive elimination (Scheme 2, b).
when 4-chlorophenylsulfonate was used as leaving group. It
was determined that the experimental data were in accord-
ance with the theoretical data explained.
The reaction conditions of the previously performed
with acetone O- (Mesitylenesulfonyl)oxime were deter-
mined as 5% CuCN catalysis at 60 min [30]. In the study
of the acetone O-(4-Chlorophenylsulfonyl)oxime, the time
was reduced to half (30 min) using the same catalyst ratio.
Moreover, arylamine yields were observed almost the same
in some reagents (Tables 1, Experiments 11 and 15). Some
of them, the yields were obtained with higher than before
the studied (Table 1, Experiments 10 and 14). Further-
more, di(4-Chloro-2-methylphenyl)cadmium and di(3,4,5-
tri(methoxy)phenyl) cadmium reagents were tested in this
study (Table 1, Experiments 17 and 18).
One of the aims of our study was to determine the ef-
cacy of acetone O-(4-Chlorophenylsulfonyl)oxime and
acetone O-(2-Naphthylsulfonyl)oxime molecules with aryl-
cadmium iodide reagents with the electrophilic amination
reactions. There are naphthyl and 4-chlorophenylsülphonate
structures as leaving groups in these molecular structures.
The naphthyl group is a larger group than the 4-chlorophe-
nyl structure. It means that the naphthyl group has a more
signifcant steric efect on the reaction mechanism. Owing
to the steric efect of the naphthyl group, it thought that
the complex formed of the oxidative addition step became
unstable. Thus, it was predicted that unstable complex for-
mation in the oxidative addition step reduced the arylamine
yield. It has been observed that the experimental yields
agree with the theoretical concepts considered. On the other
hand, the efectiveness of the leaving group 4-chlorophe-
nylsulfonate was considered. Since this structure is linear,
it was thought that it had a less steric efect in the oxida-
tive addition step compared to the naphthyl group. So, it
was thought that higher arylamine yields would be obtained
Conclusion
In this work, the ketoximes (1 and 2) were prepared and
tested in the CuCN-catalyzed electrophilic amination reac-
tion of aryl cadmium iodides, as the aminating agent. The
obtained results are the frst results about electrophilic ami-
nation of arylcadmium iodides with ketoximes. While 2 gave
functionalized anilines in moderate yields, 1 was found to be
a successful aminating agent for the synthesis of arylamines
by electrophilic amination of arylcadmium iodides, where
cadmium is not released into the environment. Especially,
when looking at the results obtained from this study, it was
determined that the structure of each amination reagent
afects the reductive elimination and oxidative addition
1 3

Journal of the Iranian Chemical Society
Scheme 2 Proposed mechanism
for the CuCN-catalyzed elec-
trophilic amination of arylcad-
mium iodides with ketoximes
CuCN
CdI
FG
CuCNCdI
CuCNCdI
a
a
FG
FG
O
S
O
S
H3C
H3C
H3C
H3C
C
N
O
C
N
O
Cl
O
O
Oxidative Addition Step
H3C CH3
H3C CH3
N
Cu O
CN
O
S
N
Cu O
CN
O
S
lll
lll
Cl
FG
FG
O
O
less steric group
more steric group
H3C CH3
H3C CH3
N
N
O
O
lll
lll
Cu O
CN
S
Cu O
CN
S
FG
FG
O
O
Reductive Elimination Step
CuCN,
Cdl(LG)
b
CH3
N
CH3
FG
1.Conc. HCl
2. PhCOCl
O
NH
FG
FG : 4-ClC6H4, 3-ClC6H4, 4-MeOC6H4, 3-MeOC6H4, 4-MeC6H4, 2-Cl-4-MeC6H3, 4-MeSC6H4,
3,5-(Cl)2C6H3, 4-FC6H4, 3,4,5-(MeO)3C6H2.
LG : -OSO2-2-C10H7, -OSO2(4-ClC6H4)
1 3

Journal of the Iranian Chemical Society
18. T. Daşkapan, Arkivoc 2011(5), 230–262 (2011)
19. J. Li, E. Tan, N. Keller, Y.H. Chen, P.M. Zehetmaier, A.C.
Jakowetz, P.J. Knochel, J. Am. Chem. Soc. 141(1), 98–103 (2018)
20. H. Gao, Z. Zhou, D.H. Kwon, J. Coombs, S. Jones, N.E. Behnke,
L. Kürti, Nat. Chem. 9(7), 681 (2017)
steps. Thus, it has been determined that the structure of the
amination reagent has an efect on the yield using diferent
functional arylcadmium reagents. As a result, it has been
observed that it can be achieved by changing the structure
of the amination reagent to synthesize the desired functional
arylamine in the best yield.
21. Z. Zhou, Z. Ma, N.E. Behnke, H. Gao, L. Kürti, J. Am. Chem.
Soc. 139(1), 115–118 (2017)
22. P. O’Brine, M.A. Malik, Science of Synthesis: In houben-weyl
methods of molecular transformations (George Thieme Verlag,
Stuttgart, Germany, 2004)
Supplementary Information The online version contains supplemen-
tary material available at https://doi.org/10.1007/s13738-021-02254-4.
23. M. Shahidzadeh, M. Ghandi, J. Organomet. Chem. 625, 108–111
(2001)
Funding This study was fnancially supported by Muş Alparslan Uni-
versity Research Foundation (Grant No. BAP-17-TBMY-4901–01).
Thereby, the author thanks Muş Alparslan University Research
Foundation.
24. T. Daşkapan, Tetrahedron Lett. 47, 2879 (2006)
25. T. Daşkapan, F. Yeşilbağ, S. Koca, Appl. Organomet. Chem. 23,
213 (2009)
26. T. Daşkapan, S. Koca, Appl. Organomet. Chem. 24, 12 (2010)
27. T. Daşkapan, S. Çiçek, Synth. Commun. 47(9), 899–906 (2017)
28. T. Daşkapan, M. Cengiz, Süleyman Demirel Üniversitesi Fen Bil-
imleri Enstitüsü Dergisi. 12(1), 9–12 (2009)
Declarations
29. E. Erdik, T. Daşkapan, Tetrahedron Lett. 43(35), 6237–6239
(2002)
Confıct of ınterest The author declares no confict of interest, fnancial
or otherwise.
30. T. Daşkapan, A. Korkmaz, Synth. Commun. 46(9), 813–817
(2016)
31. J. Wu, J. Hou, H. Yun, X. Cui, R. Yuan, J. Organomet. Chem.
637–639, 793–795 (2001)
References
32. H.J. Barber, J. Chem. Soc. 1, 79 (1943)
33. S.C. Watson, J.F. Eastham, J. Organomet. Chem. 9, 165–167
(1967)
1. K.S. Hayes, Appl. Catal. A-Gen. 221(1–2), 187–195 (2001)
2. A.W. Czarnik, Acc. Chem. Res. 29(3), 112–113 (1996)
3. A.G. MacDiarmid, Synth. Met. 84(1–3), 27–34 (1997)
4. N. Gospodinova, L. Terlemezyan, Prog. in Polym. Sci. 23(8),
1443–1484 (1998)
34. Korkmaz, A. (accepted article in the press). Copper-Catalyzed
Electrophilic Amination of Diarylcadmium Reagents Utiliz-
ing Acetone O-(4-chlorophenylsulphonyl)oxime and Acetone
O-(naphthylsulphonyl)oxime as Amination Agent. Iğdır Üniver-
sitesi Fen Bilimleri Enstitüsü Dergisi (J. of the Inst. of Sci. and
Tech.).
5. K.Y. Law, Chem. Rev. 93(1), 449–486 (1993)
6. S.A. Lawrence, Amines: Synthesis, Properties and Applications
(Cambridge University Press, United Kingdom, 2004).
7. Z. Rappoport (ed.), The Chemistry of Anilines (Wiley, England,
2007)
35. L.A. Caprino, J. Am. Chem. Soc. 82, 3133–3135 (1960)
36. H. Gilman, F. Schulze, J. Am. Chem. Soc. 47(7), 2002–2005
(1925)
37. Z. Rappoport, M. Frankel, CRC Handbook of Tables for Organic
Compound Identifcation (CRC Press, 1967), pp. 1–586
38. J. Wang, X. Yin, J. Wu, D. Wu, Y. Pan, Tetrahedron 69(48),
10463–10469 (2013)
8. V. Froidevaux, C. Negrell, S. Caillol, J.P. Pascault, Boutevin. B.
Chem. Rev. 116(22), 14181–14224 (2016)
9. E. Ciganek, Organic reactions, in Electrophilic amination of
carbanions, enolates, and their surrogates, ed. by S.E. Denmark
(Wiley, New York, 2009)
39. D.X. Zhang, S.K. Xiang, H. Hu, W. Tan, C. Feng, B.Q. Wang, H.
Yang, Tetrahedron 69(47), 10022–10029 (2013)
40. P. Du, X.K. Jiang, Z.T. Li, Tetrahedron Lett. 50(3), 320–324
(2009)
10. F. Ullmann, Dtsch. Chem. Gesellschaft 36, 2382–2384 (1903)
11. J. Liu, W. Guo, H. Sun, R. Li, Z. Feng, X. Zhou, J. Huang, Chem.
Res. Chinese Univ. 35, 457–462 (2019)
41. J. Liu, Q. Liu, H. Yi, C. Qin, R.Q.X. Bai, A. Lei, Angew. Chem.
Inter. Edit. 53(2), 502–506 (2014)
12. V. Snieckus, D.K. Kölmel, Synfacts 15(11), 1240 (2019)
13. A. Campbell Brewer, P.C. Hofman, J.R. Martinelli, M.E. Kob-
ierski, N. Mullane, D. Robbins, Org. Process Res. Dev. 23, 1484–
1498 (2019)
42. Y.C. Teo, F.F. Yong, I.K. Ithnin, S.H.T. Yio, Z. Lin, Eur. J. Org.
Chem. 2013(3), 515–524 (2013)
43. N. Yoshikai, E. Nakamura, Mechanisms of nucleophilic organo-
copper (I) reactions. Chem. Rev. 112(4), 2339–2372 (2012)
44. A.B. Gonzalez-Perez, R. Alvarez, O.N. Faza, A.R. de Lera, J.M.
Aurrecoechea, Organometallics 31(5), 2053–2058 (2012)
45. L. Liu, Z. Xi, Chin. J. of Chem. 36(12), 1213–1221 (2018)
14. L. Legnani, G. Prina Cerai, B. Morandi, ACS Catal. 6(12), 8162–
8165 (2016)
15. E.M. D’Amato, J. Börgel, T. Ritter, Chem. Sci. 10(8), 2424–2428
(2019)
16. J. Liu, K. Wu, T. Shen, Y. Liang, M. Zou, Y. Zhu, N. Jiao, Chem.
A Eur. J. 23(3), 563–567 (2017)
17. S. Munnuri, R.R. Anugu, J.R. Falck, Org. Lett. 21(6), 1926–1929
(2019)
1 3