Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with Methylarenes through Benzylic C-H Bond Oxidation

Article abstract of DOI:10.1055/s-0035-1561402

An efficient catalytic method has been developed for the synthesis of N-aroylated sulfoximines from readily available toluenes (methylarenes) as source of the aroyl coupling partner and NH-sulfoximines, employing an environmentally benign iron catalyst. T

Full text of DOI:10.1055/s-0035-1561402

SYNTHESIS
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© Georg Thieme Verlag Stuttgart · New York
2016, 48, A–I
paper
A
M. Muneeswara et al.
Paper
Synthesis
Iron-Catalyzed One-Pot N-Aroylation of NH-Sulfoximines with
Methylarenes through Benzylic C–H Bond Oxidation
Madithedu Muneeswara
R2
O
R2
NCS, MeCN
Surya Srinivas Kotha
Govindasamy Sekar*
O
O
S
S
Me
N
N
H
Ar
R1
R1
Ar
Department of Chemistry, Indian Institute of Technology
Madras, Chennai, Tamil Nadu 600 036, India
gsekar@iitm.ac.in
R1 = Ar, R2 = Me, Et
R1 = Ar, R2 = Me, Et
53–95%
FeSO4•7H2O (10 mol%)
TBHP, 85 °C
26 examples
Received: 08.10.2015
Accepted after revision: 11.02.2016
Published online: 22.03.2016
construction of various C–N bonds.7 However, for the func-
tionalization of benzylic bonds to form C(sp2)–N bonds,
there are relatively few methods available. Hydrocarbons
such as toluenes are the cheapest and most readily available
raw materials for the chemical industry. A successful devel-
opment of cross-coupling of toluenes could lead to various
synthetically useful compounds. For example, an oxidative
carbon–heteroatom bond forming strategy has been suc-
cessfully applied to the esterification, cyanation, and ami-
dation of toluenes.8
Traditionally, N-acylsulfoximines are prepared from
sulfoximines and pre-activated coupling partners such as
acyl chlorides,5a,9 aliphatic carboxylic acids,10 anhy-
drides,5d,e and benzaldehydes.11 Recently, a MnO2-mediated
aroylation of N-chlorosulfoximines employing methyl-
arenes as the source of the aroyl coupling partner was de-
scribed by Bolm and co-workers (Scheme 1).12 The reaction
failed in the case of methylarenes bearing electron-donat-
ing groups at para and ortho hindered substrates.12 Very re-
cently, Dong et al.13a and Zhao et al.13b described a transi-
tion-metal-free and an iron-catalyzed aroylation of NH-
sulfoximines with methylarenes, respectively.
Iron, a nontoxic, readily available, and inexpensive tran-
sition metal, has been successfully used as catalyst for ben-
zylic C(sp3)–H bond cross-coupling with N–H bond.14 As
part of our ongoing effort in developing an iron-catalyzed
organic transformations,15 we recently developed an iron-
catalyzed synthesis of amides from toluenes.16 Inspired by
previous results, herein we report a new route for the syn-
thesis of N-aroylsulfoximines by iron catalysis using
methylarenes as aroyl precursors (Scheme 1).
The initial study was carried out by treating S-methyl-S-
phenylsulfoximine (1a; 1 equiv) with N-chlorosuccinimide
(NCS) (1.3 equiv) in acetonitrile at room temperature for 4
hours. The resulting N-chlorosulfoximine was treated with
DOI: 10.1055/s-0035-1561402; Art ID: ss-2015-t0588-op
Abstract An efficient catalytic method has been developed for the
synthesis of N-aroylated sulfoximines from readily available toluenes
(methylarenes) as source of the aroyl coupling partner and NH-sulfoxi-
mines, employing an environmentally benign iron catalyst. This proto-
col involves oxidation of benzylic C–H bonds of toluenes to generate
aroyl radical intermediates followed by oxidative coupling with NH-sulf-
oximines to form N-aroylated sulfoximines in good to excellent yields.
The intermediate aroyl radical is successfully trapped with TEMPO to
prove the radical pathway of the reaction.
Key words iron, oxidation, amides, cross-coupling, radical reaction
Compounds containing a sulfoximine moiety have at-
tracted significant attention of chemists due to their nu-
merous use in medicinal and agricultural chemistry.1 N-Ac-
ylated sulfoximines represent one of the important classes
of sulfoximine derivatives, which have found wide applica-
tion in both biology and synthesis.2 For instance, recently
N-acylatesulfoximines were introduced in few important
bioactive pseudopeptides to provide unique secondary
structures.3 From the synthetic standpoint, sulfoximines
derivatives are being used in asymmetric synthesis as li-
gands and chiral auxiliaries.4 Likewise, N-acylated sulfoxi-
mines are utilized as a directing group for C–H bond activa-
tion.5 These potential applications increased the interest of
several research groups to develop new, efficient, and prac-
tical synthetic methods for the synthesis of sulfoximines
and their derivatives.
Cross coupling reactions that involves direct functional-
ization of unactivated C–H bonds to form C–C or C–hetero-
atom bonds have become a very efficient strategy in organ-
ic synthesis with high atom and step economy.6 Over the
past few decades, great progress has been made in the area
of oxidative coupling of C(sp)–H and C(sp2)–H bonds for the
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

B
M. Muneeswara et al.
Paper
Synthesis
Table 1 Optimization of Reaction Conditions
Previous work:
R2
N
CuBr, TBHP,
MeCN, 80 °C
O
O
O
R2
O
S
NCS (1.3 equiv)
MeCN (3 mL), 4 h
S
S
Me
O
O
O
Me
NH
+
+
+
H
R1
S
S
Bolm et al.
ref. 11
Ar
Ar
N
H
R1
Ph
Ph
N
Ph
PhMe (2a), Fe salt (10 mol%)
1a
TBHP, 85 °C, 24 h
3a
R2
N
O
O
O
MnO2, TBHP,
MeCN, 80 °C
R2
N
Me
O
S
S
Entry
Fe salt (10 mol%)
2a (equiv)
TBHP (equiv) Yield (%)
Ar
R1
Ar
Ar
Cl
H
Bolm et al.
ref. 12
R1
1
2
Fe(OAc)2
10
10
10
10
10
10
10
10
10
10
10
10
8
10
10
10
10
10
10
10
10
10
8
84
R2
N
O
FeCl2
80
R2
N
Me
O
I2, TBHP, 80 °C
S
3
FeBr2
78
Ar
R1
Dong et al.
ref. 13
R1
4
FeSO4·7H2O
FeC2O4·2H2O
FeCl3
90
5
81
R2
N
Present work:
O
O
NCS, MeCN
Me
6
86
R2
S
O
R1
S
7
Fe(acac)3
59
Ar
N
H
R1
R1 = Ar, R2 = Me, Et
Ar
8
FeNO3·9H2O
FeSO4·nH2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
–
70
R1 = Ar, R2 = Me, Et
9
73
Fe salt (10 mol%),
TBHP, 85 °C
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
91
Scheme 1 N-Aroylation of sulfoximines
8
45a
74
6
8
70
Fe(OAc)2 (10 mol%), toluene (2a; 10 equiv), and tert-butyl
hydroperoxide (TBHP, 10 equiv in decane, 5–6 M) at 85 °C
for 24 hours, in one-pot. To our delight, N-benzoylsulfoxi-
mine 3a was isolated in 84% yield (Table 1, entry 1). In order
to increase the efficiency of the oxidative cross coupling re-
action, different parameters like catalysts, reaction tem-
perature, and oxidants were screened. Among the various
iron slats examined, FeSO4·7H2O gave the higher yield of 3a
(entries 2–9). Next, the use of FeSO4·7H2O and TBHP (8
equiv) led to a maximum yield of 91% at 85 °C in MeCN (en-
try 10). When the same reaction was carried out with
aqueous TBHP, the yield of 3a was decreased to 45% (entry
11). In this reaction, more benzoic acid (1:2) was isolated
compared with the reaction using TBHP in decane (entry
10). This suggests that TBHP in water may facilitate the
overoxidation of benzaldehyde to benzoic acid. A sequential
increase (90 °C and 100 °C) or decrease (70 °C and 60 °C) of
reaction temperatures provided lower yield of 3a. Other
solvents like CH2Cl2, DCE, TCE, THF, and 1,4-dioxane were
found to be inferior compared to acetonitrile. In the ab-
sence of either Fe-catalyst or oxidant, the reaction failed to
give the product 3a. This indicates that the iron catalyst and
the oxidant are essential for this reaction. Similarly, the de-
sired product 3a was not formed in the absence of NCS,
which evidences the possible involvement of N-chlorosulf-
oximine in the reaction process (entry 20). When NBS was
used instead of NCS, the yield was reduced to 57% (entry
21). Other oxidants such as di-tert-butyl peroxide (DTBP)
and PhI(OAc)2 failed to yield the product 3a. Interestingly,
87% of N-aroylated product 3a was isolated when all re-
agents are added at the same time under optimized condi-
tions (entry 24).
10
10
10
10
10
10
10
10
10
10
10
8
70b
80c
45d
80e
ndf
nd
8
8
8
8
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
FeSO4·7H2O
–
8
ndg
57h
ndi
ndj
87k
8
–
–
8
a Reaction with aq TBHP (70% in H2O).
b Reaction with 5 mol% of Fe salt.
c Reaction with 20 mol% of Fe salt.
d Reaction at 60 °C.
e Reaction at 100 °C.
f nd: Not detected.
g Reaction without NCS.
h Reaction with NBS.
i Reaction with DTBP.
j Reaction with PhI(OAc)2.
k All reagents were added at the same time.
Subsequently, a wide range of methylarenes were ex-
amined under the optimized reaction conditions and the
results are summarized in Table 2. Halogen-substituted
methylarenes at the 3- or 4-position worked notably well
and gave the corresponding N-aroylsulfoximines in good to
excellent yields (76–95%, 3f–k). Methylarenes containing
methyl, methoxy, and nitro groups also gave products in
good yields (3b–e and 3o–r). Sterically crowded ortho-sub-
stituted (methyl or halo groups) methylarenes also success-
fully gave the corresponding N-aroylsulfoximines 3l–o in
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

C
M. Muneeswara et al.
Paper
Synthesis
Table 2 (continued)
good yields. Methylarenes containing two or more methyl
groups were selectively monoaroylated to 3o–r in good
yields.17
Entry 2
Product 3
Time Yield
(h) (%)
O
O
O
O
Me
N
Cl
Me
O
Table 2 Substrate Scope of Methylarenes
S
S
S
S
Cl
F
10
3j
24 80
24 80
24 64
48 62
24 53
24 61
18 76a
Ph
NCS (1.3 equiv)
MeCN (3 mL), 4 h
O
O
Me
NH
Me
N
O
S
S
Ph
2 (10 equiv)
Me
N
Ph
Ar
F
Me
O
FeSO4•7H2O (10 mol%)
TBHP (8 equiv), 85 °C
1a
11
3k
Ph
3a–t
Entry 2
Product 3
Time Yield
(h) (%)
Cl
Br
Me
N
Me
O
12
3l
O
Me
N
Ph
Me
O
Cl
S
S
1
3a
3b
3c
3d
24 91
18 60
24 69
36 70
Ph
Me
N
Me
O
13
3m
O
Me
N
Ph
O
Me
Br
2
Ph
MeO
O
O
O
O
F
Me
N
Me
OMe
OMe
O
S
S
S
S
14
3n
O
O
Ph
Me
N
MeO
Me
Me
O
F
S
S
3
4
5
6
7
8
9
Ph
Me
Me
N
Me
O
15
3o
Me
N
Ph
O
Me
Ph
O2N
O2N
Me
N
Me
Me
Me
O
NO2
NO2
Me
16
3p
Ph
O
O
Me
N
Me
O
S
S
3e
3f
24 73
24 95
24 80
24 78
24 76
Ph
Me
N
O
17
3q
24 85a
Ph
Me
N
Me
Me
O
Me
Me
Ph
O
Me
N
Cl
Br
I
Me
O
Cl
Br
I
S
18
3r
24 63a
Ph
O
O
O
Me
N
O
Me
S
S
S
Me
Me
3g
3h
3i
Ph
Me
Me
O
O
Me
N
O
Me
N
S
S
19
3s
3t
24 66
O
Me
Ph
Ph
Me
N
Me
O
Me
N
20
24 77
Me
O
Ph
Ph
F
a Methylarene (2 mL) was used.
F
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

D
M. Muneeswara et al.
Paper
Synthesis
When methylheteroarenes such as methylfuran, meth-
ylthiophene and methylpyridine were used as the aroylat-
ing reagents under optimized conditions, unfortunately
none of them gave the corresponding N-aroylsulfoximines.
Methylnaphthalenes under the optimized conditions suc-
cessfully afforded the corresponding products 3s and 3t in
66% and 77% yield, respectively.
The substrate scope of the sulfoximine moiety was also
investigated under the standard reaction conditions with
toluene (Table 3). S-Methyl-S-arylsulfoximines having bro-
mo, nitro, methyl, and methoxy groups 1b–f were aroylated
in good yields (69–84%, Table 3, 3u–y). S-Ethyl-S-phenyl-
sulfoximine also gave corresponding aroylated product 3z
in 63% yield.
Next, control experiments were conducted to get in-
sights into the reaction mechanism. First, the standard re-
action was carried out in the presence of radical-scavenger
BHT (3,5-di-tert-butyl-4-hydroxytoluene,
3 equiv) and
TEMPO (10 equiv). In both reactions, no N-aroylated prod-
uct 3a was formed, however, aroyl-TEMPO adduct 5 was
isolated in 99% yield in the latter reaction (Scheme 2).
When the optimization reaction was carried out in the
presence of N-chlorosulfoximine, instead of sulfoximine
and NCS, formation of 93% of N-aroylated product 3a was
observed, which evidences the involvement of N-chloro-
sulfoximine in the reaction process.
Based on the above experimental results a plausible
mechanism is proposed as shown in Scheme 3. Toluene (2a)
is likely to be oxidized to benzaldehyde 9 followed by for-
mation of aroyl radical 10 with Fe/TBHP.16,18 N-Chlorosulf-
oximine 12, generated from NH-sulfoximine by NCS, may
generate an amino radical by N–Cl bond cleavage.19 The re-
In this one-pot reaction, all three benzylic bonds of the
tolyl methyl group are activated by FeSO4·7H2O catalyst. Ini-
tially, two of the benzylic bonds of the tolyl methyl group
are converted to C=O group and the third benzylic bond is
utilized for the generation of C(sp2)–N bond.
Table 3 Substrate Scope for Sulfoximines
R2
R2
NCS (1.3 equiv)
MeCN (3 mL), 4h
O
O
O
S
S
NH
N
Ph
R1
R1
PhMe (2a; 10 equiv)
FeSO4·7H2O (10 mol%)
TBHP (8 equiv), 85 °C, 24 h
1b–g
3u–z
R1 = aryl, R2 = Me, Et
Entry
1
1
Product 3
Yield (%)
82
O
O
Me
Me
Br
S
Br
S
O
1b
1c
3u
3v
NH
N
Ph
O
O
S
Me
Me
O2N
S
O2N
S
O
2
3
69
84
NH
N
Ph
O
O
Me
Me
S
S
O
1d
1e
3w
3x
NH
N
Ph
O
Br
Br
O
O
Me
Me
NH
S
4
70
N
Ph
Me
Me
O
O
Me
Me
S
S
O
5
6
1f
3y
3z
77
63
NH
N
Ph
MeO
MeO
O
O
Et
Et
S
S
O
1g
NH
N
Ph
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

E
M. Muneeswara et al.
Paper
Synthesis
Me
N
NCS (1.3 equiv)
MeCN (3 mL), 4 h
All reactions were carried out in reaction tubes under aerobic atmo-
sphere, unless otherwise mentioned. All the solvents and chemicals
were purchased from commercial sources and used without further
purification, unless otherwise mentioned. Wherever necessary, sol-
vents were dried by standard literature procedures. Reactions were
monitored by TLC using Merck silica gel 60 F254 precoated plates (0.25
mm) and analyzed by UV fluorescence quenching using appropriate
mixture of EtOAc and hexanes as eluent. Silica gel (particle size 100–
200 mesh) purchased from SRL India was used for column chroma-
tography using hexanes and EtOAc mixture as eluent. FeSO4·7H2O,
and TBHP were purchased from Sigma-Aldrich. Thioanisoles were
purchased from TCI and Sigma-Aldrich. Reactions were carried out in
O
O
O
Me
S
S
Ph
Ph
NH
Ph
PhMe (2a; 10 equiv)
FeSO4•7H2O (10 mol%)
BHT (3 equiv)
1a
3a, not detected
TBHP (8 equiv), 85 °C
NCS (1.3 equiv)
MeCN (3 mL), 4 h
O
O
Me
NH
N
S
O
Ph
4-methylanisole (10 equiv)
FeSO4•7H2O (10 mol%)
TEMPO (10 equiv)
1a
MeO
1
temperature-controlled IKA magnetic stirrers. H and 13C NMR spec-
5, 99%
1
tra were recorded on a Bruker 400 or 500 MHz instrument. H NMR
TBHP (8 equiv), 85 °C
TEMPO adduct
spectra were reported relative to Me4Si (δ = 0.0) or residual CHCl3 (δ =
7.26). 13C NMR were reported relative to CDCl3 (δ = 77.16). FTIR spec-
tra were recorded on a Nicolet 6700 spectrometer and were reported
in frequency of absorption (cm–1). High-resolution mass spectra
(HRMS) were recorded on Q-Tof Micro mass spectrometer. All sulfoxi-
mines were synthesized according to literature procedures.5
Me
N
O
O
O
Me
N
MeCN (3 mL)
PhMe (2a; 10 equiv)
S
S
Ph
Ph
Cl
Ph
FeSO4•7H2O (10 mol%)
TBHP (8 equiv), 85 °C
3a, 93%
Sulfoximines 3a–z; General Procedure
S-Methyl-S-arylsulfoximine 1 (1 mmol) and N-chlorosuccinimide
(174 mg, 1.3 mmol) in MeCN (3 mL) were taken in an oven dried reac-
tion tube. The reaction mixture was stirred at r.t. for 4 h. To this mix-
ture were added FeSO4·7H2O (10 mol%, 28 mg), the corresponding
methylarene 2 (10 mmol), and TBHP (5–6 M in decane, 8 mmol). The
reaction mixture was stirred at 85 °C in a preheated oil bath and the
reaction was monitored by TLC. After completion of the reaction, the
solvent was removed by rotary evaporator. The resulting mixture was
washed with sat. aq Na2S2O3 (10 mL) followed by sat. aq NaHCO3 (10
mL) and extracted with EtOAc (3 × 10 mL). The combined organic lay-
ers were dried over Na2SO4 and the solvent was evaporated under re-
duced pressure. The crude mixture was purified by column chroma-
tography using hexanes/EtOAc as eluent.
Scheme 2 Control experiments
tBuOOH
+
+
OH–
+
Fe2+
Fe3+
Fe3+
Fe2+
tBuO
+
6
tBuOOH
6
7
tBuOO
H+
+
+
8
O
Fe2+
tBuOOH (6)
Ph Me
2a
Ph
H
9
O
O
tBuO
tBuOH
+
+
Ph
H
Ph
9
7
10
11
N-Benzoyl-S-methyl-S-phenylsulfoximine (3a)
Yield: 91% (236 mg); white solid; mp 122–124 °C (Lit.11 mp 122–
123 °C); Rf = 0.35 (30% EtOAc in hexanes).
R1
R1
O
O
NCS
S
S
Cl
N
H
N
R2
R2
FTIR (KBr): 1630, 1539, 1448, 1309, 1138, 967 cm–1
.
12
1H NMR (400 MHz, CDCl3): δ = 3.47 (s, 3 H), 7.41 (t, J = 7.6 Hz, 2 H),
7.50 (t, J = 7.4 Hz, 1 H), 7.61 (t, J = 7.6 Hz, 2 H), 7.68 (t, J = 7.6 Hz, 1 H),
8.03–8.09 (m, 2 H), 8.14–8.21 (m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 44.5, 127.3, 128.1, 129.6, 129.8, 132.3,
133.9, 135.7, 139.2, 174.4.
R1
R1
O
O
O
O
S
S
+
+
Cl
N
Ph
N
Cl
R2
R2
Ph
10
12
3a
HRMS: m/z [M
+
H]+ calcd for C14H14NO2S: 260.0741; found:
Scheme 3 Plausible mechanism
260.0740.
N-(4-Methoxylbenzoyl)-S-methyl-S-phenylsulfoximine (3b)
Yield: 60% (174 mg); white solid; mp 136–138 °C (Lit.11 mp 138–
139 °C); Rf = 0.36 (40% EtOAc in hexanes).
action of aroyl radical 10 with the amino radical would give
the N-aroylated sulfoximine 3a.12,13a
FTIR (KBr): 1619, 1512, 1421, 1309, 1277, 1159, 983 cm–1
.
In conclusion, we have developed a one-pot additive-
and base-free method for the N-aroylation of NH-sulfoxi-
mines using iron-catalyzed oxidative cross coupling with
methylarenes. Electron-rich and sterically hindered methyl-
arenes were successfully converted to the corresponding
products. Furthermore, the aroyl radical intermediate was
trapped with TEMPO and an aroyl-TEMPO adduct was iso-
lated to understand the radical pathway of the reaction.
1H NMR (400 MHz, CDCl3): δ = 3.45 (s, 3 H), 3.85 (s, 3 H), 6.90 (d, J =
8.8 Hz, 2 H), 7.57–7.64 (m, 2 H), 7.64–7.72 (m, 1 H), 8.02–8.08 (m, 2
H), 8.12 (d, J = 8.8 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 44.4, 55.4, 113.2, 127.2, 128.3, 129.6,
131.5, 133.7, 139.3, 162.9, 173.8.
HRMS: m/z [M + Na]+ calcd for C15H15NO3SNa: 312.0670; found:
312.0671.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

F
M. Muneeswara et al.
Paper
Synthesis
N-(3-Methoxylbenzoyl)-S-methyl-S-phenylsulfoximine (3c)
13C NMR (100 MHz, CDCl3): δ = 44.5, 127.3, 127.3, 129.9, 131.2, 131.4,
Yield: 69% (200 mg); white solid; mp 82–84 °C (Lit.13a mp 83–85 °C);
134.4, 134.6, 138.9, 173.5.
HRMS: m/z [M + Na]+ calcd for C14H12BrNO2SNa: 359.9670; found:
Rf = 0.33 (30% EtOAc in hexanes).
FTIR (KBr): 1628, 1527, 1445, 1186, 1119, 1092, 983, 758 cm–1
.
359.9674.
1H NMR (400 MHz, CDCl3): δ = 3.45 (s, 3 H), 3.83 (s, 3 H), 7.05 (dd, J =
8.0, 2.4 Hz, 1 H), 7.31 (t, J = 8.0 Hz, 1 H), 7.60 (t, J = 7.6 Hz, 2 H), 7.65–
7.71 (m, 2 H), 7.77 (d, J = 7.6 Hz, 1 H), 8.04 (d, J = 8.0 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 44.5, 55.5, 113.8, 118.9, 122.1, 127.3,
129.1, 129.8, 133.9, 137.1, 139.0, 159.5, 174.2.
N-(4-Iodobenzoyl)-S-methyl-S-phenylsulfoximine (3h)
Yield: 78% (300 mg); pale yellow solid; mp 121–123 °C (Lit.13a mp
123–125 °C); Rf = 0.31 (20% EtOAc in hexanes).
FTIR (KBr): 1619, 1582, 1480, 1378, 1138, 1010, 763 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.45 (s, 3 H), 7.61 (t, J = 7.6 Hz, 2 H),
7.69 (t, J = 7.6 Hz, 1 H), 7.75 (d, J = 8.4 Hz, 2 H), 7.86 (d, J = 8.4 Hz, 2 H),
8.03 (d, J = 7.6 Hz, 2 H).
HRMS: m/z: [M
290.0845.
+
H]+ calcd for C15H16NO3S: 290.0843; found:
N-(4-Nitrobenzoyl)-S-methyl-S-phenylsulfoximine (3d)
13C NMR (100 MHz, CDCl3): δ = 44.5, 99.9, 127.3, 129.9, 131.2, 134.0,
Yield: 70% (213 mg); pale yellow solid; mp 127–129 °C (Lit.13a mp
135.3, 137.4, 139.0, 173.7.
+
H]+ calcd for C14H13INO2S: 385.9705; found:
128–130 °C); Rf = 0.30 (40% EtOAc in hexanes).
HRMS: m/z [M
FTIR (KBr): 1641, 1512, 1421, 1357, 1186, 1122, 918 cm–1
.
385.9706.
1H NMR (400 MHz, CDCl3): δ = 3.50 (s, 3 H), 7.64 (t, J = 7.6 Hz, 2 H),
7.69–7.75 (m, 1 H), 8.03–8.07 (m, 2 H), 8.23 (d, J = 8.8 Hz, 2 H), 8.30
(d, J = 8.8 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 44.5, 123.4, 127.2, 130.0, 130.5, 134.3,
138.5, 141.2, 150.2, 172.2.
N-(4-Fluorobenzoyl)-S-methyl-S-phenylsulfoximine (3i)
Yield: 76% (211 mg); white solid; mp 112–114 °C (Lit.11 mp 110–
112 °C); Rf = 0.42 (30% EtOAc in hexanes).
FTIR (KBr): 1628, 1599, 1526, 1477, 1311, 1148, 1137, 1091, 980 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.06 (t, J = 8.8 Hz, 2 H),
7.61 (t, J = 7.6 Hz, 2 H), 7.67–7.73 (m, 1 H), 8.02–8.08 (m, 2 H), 8.13–
8.21 (m, 2 H).
HRMS: m/z [M
305.0591.
+
H]+ calcd for C14H13N2O4S: 305.0587; found:
N-(3-Nitrobenzoyl)-S-methyl-S-phenylsulfoximine (3e)
Yield: 73% (222 mg); pale yellow solid; mp 107–109 °C (Lit.13a mp
108–110 °C); Rf = 0.30 (40% EtOAc in hexanes).
13C NMR (100 MHz, CDCl3): δ = 44.5, 115.1 (J = 21.5 Hz), 127.3, 129.8,
132.0, 132.1, 134.0, 139.1, 165.6 (J = 250.6 Hz), 173.2.
HRMS: m/z [M + H]+ calcd for C14H13FNO2S: 278.0644; found:
FTIR (KBr): 1635, 1512, 1421, 1298, 1132, 972, 720 cm–1
.
278.0644.
1H NMR (400 MHz, CDCl3): δ = 3.50 (s, 3 H), 7.59 (t, J = 8.0 Hz, 1 H),
7.62–7.67 (m, 2 H), 7.71 (tt, J = 7.6, 1.2 Hz, 1 H), 8.03–8.06 (m, 2 H),
8.34 (dq, J = 8.4, 1.2 Hz, 1 H), 8.44 (dt, J = 7.6, 1.6 Hz, 1 H), 8.97 (t, J = 2
Hz, 1 H).
N-(3-Chlorobenzoyl)-S-methyl-S-phenylsulfoximine (3j)
Yield: 80% (235 mg); white solid; mp 108–110 °C (Lit.11 mp 110–
112 °C); Rf = 0.41 (30% EtOAc in hexanes).
FTIR (KBr): 1650, 1568, 1422, 1295, 1146, 1093, 982, 748 cm–1
.
13C NMR (100 MHz, CDCl3): δ = 44.6, 124.6, 126.7, 127.2, 129.3, 130.0,
1H NMR (400 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.34 (t, J = 8.0 Hz, 1 H),
7.47 (ddd, J = 8.0, 2.0, 1.2 Hz, 1 H), 7.62 (t, J = 7.7 Hz, 2 H), 7.69 (tt, J =
7.2, 1.2 Hz, 1 H), 8.01–8.07 (m, 3 H) 8.14 (t, J = 2.0 Hz, 1 H).
134.3, 135.2, 137.5, 138.5, 148.3, 171.9.
HRMS: m/z [M + Na]+ calcd for C14H12N2O4SNa: 327.0415; found:
327.0415.
13C NMR (100 MHz, CDCl3): δ = 44.5, 127.3, 127.6, 129.5, 129.7, 129.9,
N-(4-Chlorobenzoyl)-S-methyl-S-phenylsulfoximine (3f)
132.2, 134.1, 134.3, 137.6, 138.9, 173.0.
Yield: 95% (279 mg); pale yellow solid; mp 108–110 °C (Lit.12 mp
HRMS: m/z [M + Na]+ calcd for C14H12ClNO2SNa: 316.0715; found:
108–110 °C); Rf = 0.36 (30% EtOAc in hexanes).
316.0717.
FTIR (KBr): 1631, 1599, 1563, 1399, 1280, 1167, 1137, 1014, 981, 761
cm–1
.
N-(3-Fluorobenzoyl)-S-methyl-S-phenylsulfoximine (3k)
Yield: 80% (222 mg); white solid; mp 80–82 °C (Lit.13a mp 80–82 °C);
Rf = 0.40 (30% EtOAc in hexanes).
1H NMR (400 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.37 (d, J = 8.4 Hz, 2 H),
7.62 (t, J = 8.0 Hz, 2 H), 7.69 (t, J = 7.6 Hz, 1 H), 8.01–8.13 (m, 4 H).
FTIR (KBr): 1627, 1477, 1441, 1287, 1152, 1070, 985 cm–1
.
13C NMR (100 MHz, CDCl3): δ = 44.5, 127.3, 128.4, 129.9, 131.0, 133.9,
1H NMR (400 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.19 (td, J = 8.0, 2.4 Hz, 1
H), 7.37 (td, J = 8.0, 5.6 Hz, 1 H), 7.62 (t, J = 7.6 Hz, 2 H), 7.69 (tt, J = 7.6,
1.2 Hz, 1 H), 7.79 (dt, J = 8.0, 1.2 Hz, 1 H), 7.83 (ddd, J = 9.6, 2.8, 1.6 Hz,
1 H), 8.02–8.07 (m, 2 H).
134.2, 138.6, 139.0, 173.3.
HRMS: m/z [M + Na]+ calcd for C14H12ClNO2SNa: 316.0175; found:
316.0176.
N-(4-Bromobenzoyl)-S-methyl-S-phenylsulfoximine (3g)
Yield: 80% (270 mg); white solid; mp 117–119 °C (Lit.12 mp 119–
121 °C); Rf = 0.51 (30% EtOAc in hexanes).
13C NMR (100 MHz, CDCl3): δ = 44.5, 116.4 (J = 22.4 Hz), 119.2 (J = 21.3
Hz), 125.2 (J = 3.1 Hz), 127.3, 129.7 (J = 7.5 Hz), 129.9, 134.1, 138.2,
138.9, 162.7 (J = 224.6 Hz), 173.1.
HRMS: m/z [M + H]+ calcd for C14H13FNO2S: 278.0644; found:
278.0646.
FTIR (KBr): 1619, 1587, 1464, 1298, 1223, 1127, 742 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.51–7.56 (m, 2 H), 7.60–
7.65 (m, 1 H), 7.44 (tt, J = 7.2, 1.2 Hz, 1 H), 8.00–8.05 (m, 4 H).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

G
M. Muneeswara et al.
Paper
Synthesis
N-(2-Chlorobenzoyl)-S-methyl-S-phenylsulfoximine (3l)
1H NMR (400 MHz, CDCl3): δ = 2.32 (s, 3 H), 3.38 (s, 3 H), 7.22–7.24
(m, 2 H), 7.52 (t, J = 8.0 Hz, 2 H), 7.59 (t, J = 7.6 Hz, 1 H), 7.90–7.88 (m,
2 H), 7.93–8.02 (m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 21.3, 44.4, 126.6, 127.2, 128.0, 129.7,
130.0, 133.0, 133.8, 135.6, 137.7, 139.1, 174.5.
Yield: 64% (188 mg); pale yellow solid; mp 88–90 °C; Rf = 0.30 (30%
EtOAc in hexanes).
FTIR (KBr): 1624, 1464, 1427, 1298, 1223, 1138, 742 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.48 (s, 3 H), 7.29 (ddd, J = 14.0, 6.4, 2.0
Hz, 2 H), 7.33 (dd, J = 7.2, 1.6 Hz, 1 H), 7.39 (dd, J = 8.0, 1.6 Hz, 1 H),
7.59–7.69 (m, 3 H), 7.69 (tt, J = 7.6, 1.2 Hz, 1 H), 7.83 (dd, J = 7.2, 1.6
Hz, 1 H), 8.07–8.11 (m, 2 H).
HRMS: m/z [M
+
H]+ calcd for C15H16NO2S: 274.0894; found:
274.0896.
N-(4-Methylbenzoyl)-S-methyl-S-phenylsulfoximine (3q)
Yield: 85% (232 mg); white solid; mp 150–152 °C (Lit.13a mp 148–
13C NMR (100 MHz, CDCl3): δ = 44.4, 126.6, 127.4, 129.8, 130.7, 130.9,
131.3, 132.3, 134.1, 136.3, 138.5, 174.5.
150 °C); Rf = 0.43 (30% EtOAc in hexanes).
FTIR (KBr): 1614, 1581, 1312, 1281, 1134, 1093, 980, 782 cm–1
HRMS: m/z [M + Na]+ calcd for C14H12ClNO2SNa: 316.0715; found:
316.0717.
.
1H NMR (400 MHz, CDCl3): δ = 2.40 (s, 3 H), 3.46 (s, 3 H), 7.21 (d, J =
8.0 Hz, 2 H), 7.57–7.64 (m, 2 H), 7.67 (tt, J = 7.2, 1.2 Hz, 1 H), 8.03–8.09
(m, 2 Hz, 4 H).
N-(2-Bromobenzoyl)-S-methyl-S-phenylsulfoximine (3m)
Yield: 62% (210 mg); pale yellow solid; mp 83–85 °C; Rf = 0.29 (30%
EtOAc in hexanes).
13C NMR (100 MHz, CDCl3): δ = 21.8, 44.6, 127.4, 129.0, 129.8, 129.9,
FTIR (KBr): 1638, 1586, 1563, 1460, 1299, 1220, 1044, 979 cm–1
.
133.2, 134.0, 139.5, 142.9, 174.5.
1H NMR (400 MHz, CDCl3): δ = 3.48 (s, 3 H), 7.22 (dd, J = 7.6, 1.6 Hz, 1
H), 7.32 (td, J = 7.6, 1.2 Hz, 1 H), 7.56–7.65 (m, 3 H), 7.66–7.72 (m, 1
H), 7.79 (dd, J = 8.0, 2.0 Hz, 1 H), 8.08–8.13 (m, 2 H).
HRMS: m/z [M
274.0896.
+
H]+ calcd for C15H16NO2S: 274.0894; found:
N-(3,5-Dimethylbenzoyl)-S-methyl-S-phenylsulfoximine (3r)
Yield: 63% (181 mg); white solid; mp 114–116 °C (Lit.13a mp 114–
13C NMR (100 MHz, CDCl3): δ = 44.4, 120.5, 127.2, 127.4, 129.8, 130.7,
131.3, 133.8, 134.2, 138.4, 138.4, 175.1.
116 °C); Rf = 0.40 (30% EtOAc in hexanes).
FTIR (KBr): 1624, 1582, 1448, 1314, 1213 1127, 967 cm–1
HRMS: m/z [M + Na]+ calcd for C14H12BrNO2SNa: 359.9670; found:
359.9670.
.
1H NMR (400 MHz, CDCl3): δ = 2.35 (s, 6 H), 3.45 (s, 3 H), 7.14 (s, 1 H),
7.57–7.64 (m, 2 H), 7.67 (t, J = 7.6 Hz, 1 H), 7.77 (s, J = 7.7 Hz, 2 H),
8.02–8.07 (m, 2 H).
N-(2-Fluorobenzoyl)-S-methyl-S-phenylsulfoximine (3n)
Yield: 53% (147 mg); white solid; mp 109–111 °C; Rf = 0.29 (30% EtOAc
in hexanes).
13C NMR (100 MHz, CDCl3): δ = 21.2, 44.3, 127.2, 129.4, 129.7, 133.7,
FTIR (KBr): 1624, 1485, 1459, 1309, 1213, 1100, 977 cm–1
.
133.9, 135.5, 137.6, 139.2, 174.6.
+
H]+ calcd for C16H18NO2S: 288.1051; found:
1H NMR (400 MHz, CDCl3): δ = 3.48 (s, 3 H), 7.09 (t, J = 8.4 Hz, 1 H),
7.13–7.19 (m, 1 H), 7.40–7.48 (m, 1 H), 7.65–7.72 (m, 2 H), 7.68 (t, J =
7.2 Hz, 1 H), 8.00 (td, J = 7.6, 2.0 Hz, 1 H), 8.06–8.11 (m, 2 H).
HRMS: m/z [M
288.1051.
N-(1-Naphthoyl)-S-methyl-S-phenylsulfoximine (3s)
13C NMR (125 MHz, CDCl3): δ = 44.5, 116.8 (J = 22.6 Hz), 123.8 (J = 3.8
Hz), 124.5 (J = 9.4 Hz), 127.4, 129.8, 132.2, 133.4 (J = 8.8 Hz), 134.1,
138.7, 161.8 (J = 256.1 Hz), 172.3 (J = 3.6 Hz).
HRMS: m/z [M + H]+ calcd for C14H13FNO2S: 278.0644; found:
278.0646.
Yield: 66% (204 mg); pale yellow oil; Rf = 0.45 (30% EtOAc in hexanes).
FTIR (film): 1620, 1556, 1456, 1360, 1240, 1180, 1060, 960, 760 cm–1
1H NMR (500 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.44–7.50 (m, 2 H), 7.50–
7.55 (m, 1 H), 7.55–7.60 (m, 2 H), 7.61–7.68 (m, 1 H), 7.84 (d, J = 8.5
Hz, 1 H), 7.95 (d, J = 8.5 Hz, 1 H), 8.10 (d, J = 7.0 Hz, 2 H), 8.35 (d, J = 7.3
Hz, 1 H), 9.05 (d, J = 8.5 Hz, 1 H).
.
N-(2-Methylbenzoyl)-S-methyl-S-phenylsulfoximine (3o)
Yield: 61% (167 mg); white solid; mp 88–90 °C (Lit.13a mp 89–91 °C);
Rf = 0.36 (30% EtOAc in hexanes).
13C NMR (125 MHz, CDCl3): δ = 44.5, 124.6, 125.9, 126.4, 127.1, 127.2,
128.3, 129.8, 129.8, 131.3, 132.4, 132.9, 133.8, 133.9, 133.9, 138.9,
176.6.
HRMS: m/z [M + Na]+ calcd for C18H15NO2SNa: 332.0721; found:
332.0720.
FTIR (KBr): 1630, 1539, 1448, 1261, 1226, 1095, 972 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.59 (s, 3 H), 3.42 (s, 3 H), 7.21 (dd, J =
12.8, 7.6 Hz, 2 H), 7.33 (t, J = 7.4 Hz, 1 H), 7.60 (t, J = 8.4 Hz, 2 H), 7.68
(t, J = 7.4 Hz, 1 H), 8.02–8.11 (m, 2 H).
N-(2-Naphthoyl)-S-methyl-S-phenylsulfoximine (3t)
Yield: 77% (238 mg); white solid; mp 120–122 °C (Lit.13a mp 120–
13C NMR (100 MHz, CDCl3): δ = 21.7, 44.5, 125.4, 127.2, 129.7, 130.6,
130.9, 131.5, 133.7, 135.3, 139.2, 139.3, 176.5.
122 °C); Rf = 0.49 (30% EtOAc in hexanes).
FTIR (KBr): 1627, 1560, 1440, 1320, 1260, 1120, 980, 762 cm–1
HRMS: m/z [M + Na]+ calcd for C15H15NO2SNa: 296.0721; found:
296.0721.
.
1H NMR (500 MHz, CDCl3): δ = 3.51 (s, 3 H), 7.53 (dt, J = 7.0, 15.0 Hz, 2
H), 7.63 (t, J = 7.2 Hz, 2 H), 7.70 (t, J = 7.0 Hz, 1 H), 7.82–7.791 (m, 2 H),
7.96 (d, J = 8.0 Hz, 1 H), 8.10 (d, J = 8.0 Hz, 2 H), 8.20 (d, J = 8.5 Hz, 1 H).
N-(3-Methylbenzoyl)-S-methyl-S-phenylsulfoximine (3p)
Yield: 76% (208 mg); white solid; mp 57–59 °C (Lit.13a mp 57–59 °C);
Rf = 0.31 (30% EtOAc in hexanes).
13C NMR (125 MHz, CDCl3): δ = 44.5, 125.7, 126.4, 127.3, 127.8, 127.8,
FTIR (KBr): 1624, 1578, 1288, 1121, 1085, 978, 753 cm–1
.
127.9, 129.5, 129.8, 130.7, 132.7, 133.0, 133.9, 135.5, 139.2, 174.5.
HRMS: m/z [M + Na]+ calcd for C18H15NO2SNa: 332.0721; found:
332.0755.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

H
M. Muneeswara et al.
Paper
Synthesis
N-Benzoyl-S-methyl-S-(3-bromophenyl)sulfoximine (3u)
13C NMR (100 MHz, CDCl3): δ = 44.8, 55.9, 115.0, 128.1, 129.5, 129.5,
Yield: 82% (277 mg); pale yellow solid; mp 146–148 °C (Lit.12 mp
130.0, 132.2, 135.8, 164.0, 174.4.
HRMS: m/z [M + Na]+ calcd for C15H15NO3SNa: 312.0670; found:
147–149 °C); Rf = 0.49 (30% EtOAc in hexanes).
FTIR (KBr): 1627, 1506, 1456, 1399, 1317, 1064, 1017, 717 cm–1
.
312.0670.
1H NMR (400 MHz, CDCl3): δ = 3.46 (s, 3 H), 7.38–7.56 (m, 4 H), 7.80
(dq, J = 8.0, 0.8 Hz, 1 H), 7.98 (dq, J = 8.0, 0.8 Hz, 1 H), 8.13–8.21 (m, 3
H).
N-Benzoyl-S-ethyl-S-phenylsulfoximine (3z)
Yield: 63% (173 mg); white solid; mp 118–120 °C (Lit.13a mp 118–
120 °C); Rf = 0.35 (30% EtOAc in hexanes).
FTIR (KBr): 1570, 1441, 1320, 1260, 1120, 1080, 930, 730 cm–1
13C NMR (100 MHz, CDCl3): δ = 44.5, 123.8, 125.9, 128.2, 129.6, 130.3,
131.3, 132.5, 135.4, 137.1, 141.2, 174.3.
.
1H NMR (400 MHz, CDCl3): δ = 1.30 (t, J = 7.2 Hz, 3 H), 3.60 (q, J = 7.2
Hz, 2 H), 7.38–7.44 (m, 2 H), 7.50 (tt, J = 1.2, 8.8 Hz, 1 H), 7.56–7.63
(m, 2 H), 7.67 (tt, J = 1.2, 8.8 Hz, 1 H), 7.95–8.04 (m, 2 H), 8.14–8.22
(m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 7.4, 50.7 128.1, 128.1, 129.5, 129.7,
132.2, 133.8, 135.7, 136.5, 174.3.
HRMS: m/z [M + Na]+ calcd for C14H12BrNO2SNa: 359.9670; found:
359.9670.
N-Benzoyl-S-methyl-S-(3-nitrophenyl)sulfoximine (3v)
Yield: 69% (210 mg); pale yellow solid; mp 142–145 °C; Rf = 0.31 (40%
EtOAc in hexanes).
HRMS: m/z [M + Na]+ calcd for C15H15NO2SNa: 296.0721; found:
296.0720.
FTIR (KBr): 1641, 1581, 1541, 1345, 1070, 974, 717 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.50 (s, 3 H), 7.41 (t, J = 8.0 Hz, 2H),
7.50–7.55 (m, 1 H), 7.83 (t, J = 8.0 Hz, 1 H), 8.09–8.15 (m, 2 H), 8.34–
8.39 (m, 1 H), 8.50 (dq, J = 6.4, 1.0 Hz, 1 H), 8.85 (t, J = 2.0 Hz, 1 H).
2,2,6,6-Tetramethylpiperidin-1-yl 4-Methoxybenzoate (5)15
Yield: 99% (290 mg); yellow oil; Rf = 0.52 (30% EtOAc in hexanes).
13C NMR (100 MHz, CDCl3): δ = 44.2, 122.8, 128.3, 128.4, 129.6, 131.3,
132.7, 132.9, 134.9, 141.6, 148.8, 174.3.
FTIR (film): 1167, 2931, 3414 cm–1
.
1H NMR (CDCl3, 400 MHz): δ = 1.09 (s, 6 H), 1.24 (s, 6 H), 1.37–1.47
(m, 1 H), 1.49–1.60 (m, 2 H), 2.60–1.82 (m, 3 H), 3.84 (s, 3 H), 6.90–
6.94 (m, 2 H), 7.90–8.03 (m, J = 9.2 Hz, 2 H).
HRMS: m/z [M
327.0413.
+
Na]+ calcd C14H12N2O4SNa: 327.0415; found:
N-Benzoyl-S-methyl-S-(4-bromophenyl)sulfoximine (3w)
13C NMR (CDCl3, 125 MHz): δ = 17.1, 20.9, 32.0, 39.1, 55.6, 60.4, 113.8,
Yield: 84% (284 mg); pale yellow solid; mp 146–148 °C (Lit.12 mp
122.0, 131.7, 163.4, 166.2.
HRMS: m/z [M + H]+ calcd for C17H26NO3: 292.1913; found: 292.1913.
147–149 °C); Rf = 0.49 (30% EtOAc in hexanes).
FTIR (KBr): 1627, 1621, 1452, 1310, 1224, 1117, 1020, 967 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.44 (s, 3 H), 7.41 (t, J = 8.0 Hz, 2 H),
7.48–7.55 (m, 1 H), 7.69–7.78 (m, 2 H), 7.86–7.94 (m, 2 H), 8.10–8.17
(m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 44.5, 128.2, 128.9, 129.3, 132.5, 133.1,
135.4, 138.2, 174.3.
Acknowledgment
We thank DST (project No. SB/S1/OC-72/2013) and DST Nanomission
(SR/NM/NS-1034/2012(G)) for financial support. M.M. thanks UGC,
New Delhi for a senior research fellowship and K.S.S. thanks CSIR,
New Delhi for a senior research fellowship.
HRMS: m/z [M + Na]+ calcd for C14H12BrNO2SNa: 359.9670; found:
359.9674.
Supporting Information
N-Benzoyl-S-methyl-S-(4-methylphenyl)sulfoximine (3x)
Yield: 70% (191 mg); white solid; mp 93–95 °C (Lit.13a mp 92–94 °C);
Rf = 0.38 (30% EtOAc in hexanes).
Supporting information for this article is available online at
http://dx.doi.org/10.1055/s-0035-1561402.
S
u
p
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o
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f
rmoaitn
S
u
p
p
ortiInfogrmoaitn
FTIR (KBr): 1629, 1539, 1448, 1226, 1127, 1086, 967, 787 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.45, (s, 3 H), 3.45 (s, 3 H), 7.36–7.44
(m, 4 H), 7.50 (tt, J = 1.2, 7.2 Hz, 1 H), 7.93 (d, J = 8.4 Hz, 2 H), 8.16 (d,
J = 8.4 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 21.7, 44.6, 127.3, 128.1, 129.5, 130.4,
132.2, 135.8, 136.0, 145.0, 174.4.
References
(1) (a) Park, S. J.; Baars, H.; Mersmann, S.; Buschmann, H.; Baron, J.
M.; Amann, P. M.; Czaja, K.; Hollert, H.; Bluhm, K.; Redelstein,
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HRMS: m/z [M + Na]+ calcd for C15H15NO2SNa: 296.0721; found:
296.0720.
N-Benzoyl-S-methyl-S-(4-methoxylphenyl)sulfoximine (3y)
Yield: 77% (223 mg); white solid; mp 82–84 °C (Lit.13a mp 83–85 °C);
Rf = 0.34 (40% EtOAc in hexanes).
FTIR (KBr): 1629, 1512, 1492, 1280, 1210, 1028, 980 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 3.45 (s, 3 H), 3.88 (s, 3 H), 7.06 (d, J =
8.8 Hz, 2 H), 7.40 (t, J = 7.6 Hz, 2 H), 7.50 (tt, J = 1.2, 8.8 Hz, 1 H), 7.97
(d, J = 9.2 Hz, 2 H), 8.17 (d, J = 7.6 Hz, 2 H).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I

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M. Muneeswara et al.
Paper
Synthesis
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I