Sulfoximinocarbonylation of aryl halides using heterogeneous Pd/C catalyst

Article abstract of DOI:10.1039/c6ra21732j

A three component protocol has been developed for the synthesis of N-aroyl sulfoximines by the carbonylation of aryl halides followed by nucleophilic attack of NH-sulfoximines. This reaction tolerates a range of aryl iodides and sulfoximines to provide th

Full text of DOI:10.1039/c6ra21732j

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DOI: 10.1039/C6RA21732J
Journal Name
ARTICLE
Sulfoximinocarbonylation of aryl halides using heterogeneous
Pd/C catalyst
Received 00th January 20xx,
Accepted 00th January 20xx
Balasubramanian Devi Bala, Nidhi Sharma and Govindasamy Sekar*
A three component protocol has been developed for the synthesis of N-aroyl sulfoximines by the carbonylation of aryl
halides followed by nucleophilic attack of NH-sulfoximine. This reaction abides a range of aryl iodides and sulfoximines to
provide the N-aroyl sulfoximine in good to excellent yields. Less reactive aryl bromide also underwent
sulfoximinocarbonylation and afforded the products. This methodology is free from phosphine ligands. The heterogeneous
Pd/C catalyst was successfully recovered and reused up to five consecutive catalytic cycles.
DOI: 10.1039/x0xx00000x
www.rsc.org/
catalytic activity.13 Recently, Pd/C catalyzed carbonylation
reaction has received much attention which includes carbon
monoxide and the corresponding surrogates for the synthesis
Introduction
Carbonylation reactions exploiting carbon monoxide (CO) as
C1-building block is one of the important tools for constructing
myriad carbonyl compounds in both academia and industry.1
In particular, several reports have been advanced on the utility
of carbonyl-installing reactions, such as aminocarbonylation,
of various carbonyl compounds.14
Sulfoximines are isoelectronic with sulfones and they are
mono aza analogues of sulfones where S=N unit replaces one
of the two S=O units, which deal a versatile chemistry.15 They
serve as pharmacophores and display diverse bioactivities16a
like, HIV-1 protease inhibitors,16b pan-CDK inhibitors (anti-
cancer drug),16c antiasthmatics,16d,e and antiproliferatives.16f,g
Sulfoximines are also recognized for their application in
agricultural chemistry (crop protection),17 chiral auxiliaries
and ligands in asymmetric synthesis.18 N-functionalization of
sulfoximine would allow synthetic diversity, specific reactivity
and change in chemical as well as physical properties.15b N-
alkoxycarbonylation,2
thio-carbonylation,3
oxidative
carbonylation,4 double carbonylation,5 carbonylative α-
arylation,6 carbonylative Heck,7 carbonylative Suzuki- Miyaura8
and carbonylative C-H activation.9 Though Pd-catalyzed
carbonylation reactions have been well travelled over the past
decades, these reactions still attract a great deal of attention
as CO is inexpensive, readily available, unique reactive and a
versatile C1-unit.10 The quest for carbonylation reaction
continues with the objective of increasing the diversity of
possible substrates, catalyst-product separation techniques
and the recovery of pricy metal catalysts.
aroyl sulfoximines,
a class of sulfoximine have been
conventionally achieved from aroyl chlorides and NH-
sulfoximines.19 Bolm and other research groups made more
advancement in this area, switching acid chlorides to
aldehydes or methyl arenes.20
In homogeneous Pd catalysis, recycling of the expensive Pd
and contamination by residual palladium in the final products
are often the major disadvantages. Also, Pd catalyst often
needs expensive and easily oxidizable phosphine ligands. The
practice of heterogeneous catalyst will overcome these
difficulties, especially palladium on carbon (Pd/C) is one of the
most common heterogeneous catalyst which has gained a
considerable attention in green and sustainable chemistry.11
Wide commercial availability, recoverability, reusability,
relatively low cost and the avoidance of residual metal in the
desired product, have crafted Pd/C as an interesting catalytic
system.12 Several literature precedents of Pd/C-catalyzed C-C
and C-X (X=N, S or O) bond forming reactions signify its
Recently, we reported palladium nanoparticle (Pd-BNP)
catalyzed sulfoximinocarbonylation of aryl iodide with carbon
monoxide which afforded aroylation of NH-sulfoximines.
Although we have witnessed broad substrate scope and
reusability of nanocatalyst, the synthesis of Pd-BNP limits this
methodology to be more widely applied.21 Consequently,
herein we report a protocol using commercially available
heterogenous Pd/C for the assembly of N-aroyl sulfoximine
from aryl iodides/bromides, carbon monoxide and NH-
sulfoximine (Scheme 1).
Department of Chemistry, Indian Institute of Technology Madras, Chennai,
Tamil Nadu, India. Fax: (+91)-44-2257-4202; e-mail: gsekar@iitm.ac.in
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
Scheme
halides.
1
Heterogeneous Pd/C catalyzed sulfoximinocarbonylation of aryl
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
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base equivalents from 1 to 0.5 and 2 equivalents were also not
fruitful (entries 18 and 19). Increase in the amount of catalyst
Results and Discussion
View Article Online
DOI: 10.1039/C6RA21732J
At the outset, 4-iodotoluene 1a and S-methyl-S-phenyl-
sulfoximine 2a were chosen as the model substrates to
optimize the reaction condition. The reaction of 1a and 2a with
1 mol% of Pd/C and 1 equiv. of K2CO3 under CO balloon in DMF
solvent at ambient temperature afforded the product 3a in
34% yield (Table 1, entry 1). Fortunately, higher yields of 3a
loading from 1 mol% to 2 mol% of Pd/C had no significant
effect on the yield. While decrease in the catalyst loading to
0.5 mol%, the yield of the product was decreased to 67%
(entry 22). It is important to note that the reaction in the
absence of base afforded 31% of 3a and no product formation
was observed in the absence of Pd/C (entries 20 and 21).
o
could be obtained by performing the same reaction at 60 C
Having suitable optimized conditions in hand (Table 1, entry 2),
the scope of the sulfoximinocarbonylation with regard to aryl
iodide was next studied (Table 2). The generality of this
method is proven by the reaction of 2a with different
substrates, which afforded the desired products (3a-s) in good
to excellent yields. Aryl iodides bearing electron-donating
substituents (Me, OMe and SMe) (3a-e) as well as electron-
withdrawing substituents (CN, CF3 and COOMe) (3k-o) resulted
into good yield of N-aroyl sulfoximines. The carbonylation
reaction of para, meta and ortho-substituted iodoarenes took
place readily and delivered the products in good yields.
yielding 91% of the product (entry 2). Further increasing the
reaction temperature to 80 C has no effect on time and yield
of 3a (entry 3). In next exploration steps, solvent effect on this
carbonylation was examined and it clearly shows that among
various solvents employed in the transformation, none of
them gave better yield than DMF (entries 4-10).
o
Table 1 Optimization of reaction condition for sulfoximino carbonylationa
Sulfoximinocarbonylation
of
iodobenzene
and
1-
iodonapthalene also afforded the desired products 3f
92% and 94% yields respectively.
,
3q in
Entry
1
Solvent
DMF
Base (equiv)
K2CO3 (1)
Time (h)
24
Yieldb (%)
34c
Table 2 Synthesis of N-aroyl sulfoximines with different aryl iodidesa,b
2
DMF
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
Cs2CO3 (1)
Na2CO3 (1)
NaOEt (1)
KOtBu (1)
K3PO4 (1)
Et3N (1)
7
91
90c
68
31
71
53
76
49
73
74
76
67
84
80
41
52
56
88
31d
-- e
67f
89g
3
DMF
7
4
Toluene
DCE
12
12
10
8
5
6
THF
7
MeCN
2-Me THF
Water
PEG-600
DMF
8
12
10
7
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
10
10
9
DMF
DMF
DMF
12
10
12
12
20
7
DMF
DMF
DMF
DABCO (1)
K2CO3 (0.5)
K2CO3 (1.5)
--
DMF
DMF
DMF
30
24
16
6
DMF
DMF
K2CO3 (1)
K2CO3 (1)
K2CO3 (1)
DMF
a Reaction conditions: 0.5 mmol of 1a, 0.75 mmol of 2a, CO balloon and 1
c
mol% of 10 wt% Pd/C (5.3 mg) in 1 mL of solvent at 60 oC. b Isolated yield.
Reaction at rt for entry 1 and at 80 oC for entry 3. d Reaction without base. e
Reaction without Pd/C. 0.5 mol% of Pd/C was used. g 2 mol% of Pd/C was
f
used.
To further improve the yield, various bases were screened.
Cs2CO3 and Na2CO3 gave lower yields than K2CO3 (entries 11
and 12). Strong bases like NaOEt and KOtBu were also failed to
improve the yield (entries 13 and 14). Organic bases such as
Et3N and DABCO provided diminished yield 41% and 52% of
the product respectively (entries 16 and 17). Changing the
a Reaction conditions: 0.5 mmol of 1, 0.75 mmol of 2a, CO balloon, 1 mL of DMF. b
Isolated yield. c 4.6 mmol of 1a, 6.9 mmol of 2a in 10 mL of DMF.
2 | J. Name., 2012, 00, 1-3
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Iodoarenes having other halogen substitution like bromo, few more bromoarenes were investigated under tVhieewoAprtitcilme Oiznleinde
DOI: 10.1039/C6RA21732J
chloro and fluoro groups were observed to give only the mono conditions and the results are given in Table 4. The
N-aroylated products in very good yield (3g-j). o-Iodophenol sulfoximinocarbonylation of heteroaryl bromides like 2-
underwent this carbonylation and afforded the product in bromopyridine, 3-bromopyridine and 5-bromoindole failed to
moderate yield of 61%. Heteroaryl substrate like 2- occur.
iodothiophene was also efficiently transformed in this
optimized condition furnished the product 3r in 79% yield.
Delightfully, the double carbonylation of 1,4-diiodobenzene
proceeded smoothly and afforded desired N-aroyl sulfoximine
3s in 88% yield. However, the carbonylation reaction of
heteroaryl iodies like 2-iodopyridine, 3-iodopyridine and 3-
iodo-1-methyl-1H-indole failed to provide the desired product.
To investigate the versatility of this methodology, a gram scale
reaction of 1a (1g) was performed with 2a under optimized
condition, and it afforded N-(4-methylbenzoyl)-S-methyl-S-
phenyl sulfoximine (3a) in 88% yield (Table 2) proving its
efficiency and practical utility.
Having established a good scope with aryl iodides, the
optimized reaction condition was then applied to NH-
sulfoximines having substituents at the aryl ring. The
substituents such as methoxy, bromo and chloro, were
applicable for this carbonylation reaction and afforded the
product in good to excellent yields (Table 3, 3t-z and 3aa). S-
Table 4 Synthesis of N-aroyl sulfoximines with different aryl bromidesa,b
a
Reaction conditions: 0.5 mmol of 1, 0.75 mmol of 2a, CO balloon, in 1 mL of
DMF. b Isolated yield.
A
plausible mechanism for the sulfoximinocarbonylation
reaction of aryl iodide is depicted in Scheme 2.22 Initially Pd(0)
undergoes oxidative addition with aryl iodide to afford which
upon CO insertion furnish the acylpalladium complex
Presumably nucleophilic attack of sulfoximine to forms
intermediate . Finally, reductive elimination expelled the N-
5
6
.
ethyl-S-phenyl-NH-sulfoximine
also
provided
the
6
corresponding N-aroyl sulfoximine 3ab in good yield.
7
aroyl sulfoximine and regenerated the active Pd(0) catalyst.
Table 3 Synthesis of N-aroyl sulfoximines with different NH-sulfoximinesa,b
Scheme 2 Plausible mechanism for Pd/C-catalyzed sulfoximinocarbonylation of aryl
halide.
The reusability of Pd/C would make this process economically
and environmentally benign. Thus we next tested the
recyclability of the catalyst for carbonylation reaction of 4-
iodotoluene 1a and S-methyl-S-phenyl-sulfoximine 2a under
standard reaction condition. Pd/C has been easily recovered by
centrifugation of reaction mixture and washed with nanopure
water, methanol and dried under vacuum. The recovered
catalyst shows good catalytic activity up to five reaction cycles
(Table 5).
a Reaction conditions: 0.5 mmol of 1, 0.75 mmol of 2b, CO balloon, 1 mL of DMF.
b Isolated yield.
These results prompted to expand the scope of the
sulfoximinocarbonylation with less reactive aryl bromides.
Initial attempts to apply the above optimized reaction
conditions to aryl bromide was unsuccessful. However,
increasing the reaction temperature to 100 oC and higher
catalyst loading helped to acquire the desired product. Next,
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1138, 1220, 1446, 1573, 1628, 2925, 3021 cm ; MS (m/z):
Table 5 Recycling of Pd/C catalyst
View Article Online
[M]+: 273.00.
DOI: 10.1039/C6RA21732J
N-(3-Methylbenzoyl)-S-methyl-S-phenylsulfoximine
(3b):21
Yield 81%; 110 mg; pale white solid; mp 75-77 oC [lit.78-80
oC];21 Rf 0.42 (30% ethyl acetate in hexanes); H NMR (CDCl3,
1
400 MHz) δ 2.39 (s, 3H), 3.46 (s, 3H), 7.27-7.35 (m, 2H), 7.57-
7.65 (m, 2H), 7.67-7.72 (m, 1H), 7.93-8.01 (m, 2H), 8.03-8.08
(m, 2H); 13C NMR (CDCl3, 100 MHz) δ 21.3, 44.3, 126.6, 127.2,
128.0, 129.7, 130.0, 133.0, 133.8, 135.6, 137.7, 139.1, 174.5;
FTIR (KBr) 749, 979, 1125, 1213, 1447, 1583, 1627, 2926, 3023
cm-1; MS (m/z): [M]+ 273.00.
Run
1
91
2
89
3
90
4
88
5
85
Yield (%)a
a Isolated yield.
N-(3-Methoxybenzoyl)-S-methyl-S-phenylsulfoximine (3c):21
Yield 84%; 121 mg; pale white solid; mp 90-92 oC [lit.92-94
The reaction mixture after fifth cycle was examined by ICP-OES
analysis. ICP analysis revealed that no detectable amount of
palladium (0.02 ppm) was present in the reaction mixture
which shows no significant leaching of palladium and it was
further confirmed by hot filtration test and mercury poisoning
test.23
1
oC];21 Rf 0.45 (40% ethyl acetate in hexanes); H NMR (CDCl3,
400 MHz) δ 3.45 (s, 3H), 3.83 (s, 3H), 7.01-7.10 (m, 1H), 7.31 (t,
J =8.0 Hz, 1H), 7.56-7.64 (m, 2H), 7.65-7.71 (m, 2H), 7.79 (d, J=
7.6 Hz, 1H), 8.04 (d, J = 7.6 Hz, 2H); 13C NMR (CDCl3, 100 MHz)
δ 44.4, 55.5, 113.9, 118.8, 122.1, 127.2, 129.1, 129.8, 133.9,
137.1, 139.0, 159.5, 174.1; FTIR (KBr) 759, 982, 1119, 1222,
1285, 1580, 1627, 2931, 3012 cm-1; MS (m/z): [M]+ 289.00.
N-(3,4,5-Trimethoxybenzoyl)-S-methyl-S-phenylsulfoximine
(3d):21 Yield 87%; 152 mg; white solid, mp 136-138 oC [lit. 140-
142 oC];21 Rf 0.27 (40% ethyl acetate in hexanes); 1H NMR
(CDCl3, 400 MHz) δ 3.45 (s, 3H), 3.89 (s, 9H), 7.44 (s, 2H), 7.58-
7.64 (m, 2H), 7.65-7.71 (m, 1H), 8.00-8.06 (m, 2H); 13C NMR
(CDCl3, 100 MHz) δ 44.4, 56.3, 61.0, 106.7, 127.2, 129.8, 130.9,
133.9, 141.7, 152.7, 173.8; FTIR (KBr) 762, 998, 1127, 1224,
1335, 1580, 1624, 2935, 3006 cm-1; HRMS (m/z): [M+Na]+
calcd. for C17H19NO5SNa: 372.0882; found: 372.0875.
Conclusion
In conclusion, the present study demonstrates Pd/C as an
efficient heterogenous catalyst for the suloximino
carbonylation of aryl halides. The developed procedure allows
wide range of electron rich and poor substrates and furnished
the N-aroylated sulfoximines in moderate to excellent yields.
Further developement of this statergy with slight modified
condition on aryl bromides afforded the product in moderate
yield. The recyclability of Pd/C up to five reaction cycles
without significant loss in its catalytic activity makes this
methodology valuable for environmental and economic
concerns.
N-((2-Methylthio)benzoyl)-S-methyl-S-phenylsulfoximine
(3e):21 Yield 80%; 122 mg; colourless viscous liquid; Rf 0.30
1
(30% ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ
2.37 (s, 3H), 3.44 (s, 3H), 7.10 (t, J = 7.6 Hz, 1H), 7.21 (d, J = 8.0
Hz, 1H), 7.35-7.41 (m, 1H), 7.55 (t, J = 8.4 Hz, 2H), 7.59-7.65
(m, 1H), 8.03 (d, J= 7.6 Hz, 2H), 8.17 (dd, J= 8.0, 1.6 Hz, 1H); 13
C
Experimental Section
General Procedure for the synthesis of N-aroyl sulfoximine 3
NMR (CDCl3, 100 MHz) δ 15.8, 44.3, 123.2, 124.1, 127.2, 129.6,
131.6, 131.7, 132.5, 133.8, 138.7, 142.2, 174.6; FTIR (Neat)
Aryl iodide 1 (0.5 mmol), NH-sulfoximine 2
(0.75 mmol), 713, 978, 1136, 1220, 1447, 1577, 1627, 2925, 3062 cm-1; MS
Pd/C (5.3 mg) (1 mol%) and K2CO3 (0.5 mmol) were taken in a (m/z): [M]+ 305.00.
reaction tube with magnetic pellet and covered using septum. N-Benzoyl-S-methyl-S-phenylsulfoximine (3f):21 Yield 92%;
o
o
It was first evacuated (10 min) and DMF (1 mL) was added, 119 mg; white solid, mp 114-116 C [lit.120-122 C];21 Rf 0.36
1
again it was evacuated (10 min). CO balloon was introduced (30% ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ
o
and stirred at 60 C until the completion of the reaction (TLC). 3.42 (s, 3H), 7.35-7.41 (m, 2H), 7.48 (tt, J = 7.6, 1.2 Hz, 1H),
After completion, the reaction mixture was first extracted with 7.54-7.60 (m, 2H), 7.64 (tt, J = 7.6, 1.2 Hz, 1H), 7.99-8.06 (m,
ethyl acetate (3 X 5 mL), followed by brine solution. Then the 2H), 8.13-8.19 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.3,
organic layer was dried over Na2SO4 and concentrated under 127.1, 128.0, 129.4, 129.7, 132.2, 133.8, 135.5, 138.8, 174.2;
vacuum. The crude reaction mixture was purified by column FTIR (KBr) 713, 978, 1136, 1220, 1447, 1577, 1627, 2925, 3062
chromatography on silica gel (hexanes:ethyl acetate) to get N- cm-1; MS (m/z): [M]+ 258.75.
aroyl sulfoximine
3
.
N-(4-Chlorobenzoyl)-S-methyl-S-phenylsulfoximine
(3g):21
o
Yield 82%; 120 mg; white solid; mp 111-113 C [lit. 114-116
N-(4-Methylbenzoyl)-S-methyl-S-phenyl sulfoximine (3a):21
1
oC];21 Rf 0.42 (30% ethyl acetate in hexanes); H NMR (CDCl3,
Yield 91%; 124 mg; white solid; mp 161-163 oC [lit.168-169
400 MHz) δ 3.47 (s, 3H), 7.38 (d, J= 8.4 Hz, 2H), 7.59-7.66 (m,
2H), 7.40 (tt, J= 7.2, 1.2 Hz, 1H), 8.01-8.06 (m, 2H), 8.10 (d, J=
8.4 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.5, 127.2, 128.4,
129.9, 131.0, 134.0, 134.2, 138.6, 138.9, 173.3; FTIR (KBr) 763,
836, 978, 1136, 1281, 1588, 1627, 2926, 3065 cm-1; MS (m/z):
[M]+ 292.70.
oC];21 Rf 0.40 (30% ethyl acetate in hexanes); H NMR (CDCl3,
1
400 MHz) δ 2.39 (s, 3H), 3.45 (s, 3H), 7.20 (d, J = 8.0 Hz, 2H),
7.56-7.62 (m, 2H), 7.63-7.70 (m, 1H), 8.00-8.08 (m, 4H); 13C
NMR (CDCl3, 100 MHz) δ 21.7, 44.4, 127.2, 128.8, 129.6, 129.7,
133.0, 133.8, 139.2, 142.8, 174.3; FTIR (KBr) 757, 840, 983,
4 | J. Name., 2012, 00, 1-3
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N-(3-Fluorobenzoyl)-S-methyl-S-phenylsulfoximine (3h):21
ARTICLE
N-(3-Nitrobenzoyl)-S-methyl-S-phenylsulfoximine (3n):21
View Article YOinelinlde
o
Yield 74%; 102 mg; white solid; mp 79-81 oC [lit. 86-88 oC];21 Rf 84%; 127 mg; pale yellow solid; mp 102-104 C [lit. 103-105
DOI: 10.1039/C6RA21732J
1
1
0.39 (30% ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) oC];21 Rf 0.44 (40% ethyl acetate in hexanes); H NMR (CDCl3,
δ 3.45 (s, 3H), 7.18 (tdd, J = 8.4, 2.8, 0.8 Hz, 1H), 7.32-7.41 (m, 400 MHz) δ δ 3.48 (s, 3H), 7.56 (d, J= 8.0 Hz, 1H), 7.59-7.66
1H), 7.56-7.64 (m, 2H), 7.67 (tt, J = 7.6, 1.2 Hz, 1H), 7.79-7.85 (m, 2H), 7.67-7.72 (m, 1H), 7.99-8.06 (m, 2H), 8.31 (ddd, J= 8.4,
(m, 1H), 7.93 (dt, J = 8.0, 1.2 Hz, 1H), 7.99-8.05 (m, 2H); 13C 6.4, 1.2 Hz, 1H), 8.42 (dt, J= 7.6, 1.2 Hz, 1H), 8.94 (t, J= 1.6 Hz,
NMR (CDCl3, 100 MHz) δ 44.4, 116.2 (d, JC-F = 22.0 Hz), 119.1 1H); 13C NMR (CDCl3, 100 MHz) δ 44.4, 124.4, 126.6, 127.1,
(d, JC-F = 21.0 Hz), 125.1 (d, JC-F = 3.0 Hz), 127.2, 129.6, 129.8, 129.2, 129.9, 134.2, 135.1, 137.4, 138.2, 148.1, 171.8;
134.0, 138.0 (d, JC-F = 7.0 Hz), 138.7, 162.6, (d, JC-F = 245 Hz), FTIR(KBr) 720, 981, 1152, 1291, 1528, 1631, 2921, 3050 cm-1;
173.0 (d, JC-F = 2.0 Hz); 19F NMR (CDCl3, 470 MHz) δ -116.5; HRMS (m/z): [M+Na]+ calcd. for C14H12N2O4SNa: 327.0415;
FTIR (KBr) 760, 813, 982, 1110, 1220, 1291, 1587, 1629, 2930, found: 327.0406.
3020 cm-1; MS (m/z): [M]+ 277.05.
N-(4-Methylcarbonylesterbenzoyl)-S-methyl-S-phenyl
N-(3-Chlorobenzoyl)-S-methyl-S-phenylsulfoximine (3i):21
sulfoximine (3o):21 Yield 90%; 142 mg; white solid; mp 122-124
o
Yield 77%; 113 mg; white solid; mp 101-103 C [lit. 106-108 oC [lit. 121-123 oC];21 Rf 0.48 (40% ethyl acetate in hexanes); 1H
1
oC];21 Rf 0.40 (30% ethylacetate in hexanes); H NMR (CDCl3, NMR (CDCl3, 400 MHz) δ 3.47 (s, 3H), 3.91 (s, 3H), 7.57-7.65
400 MHz) δ 3.46 (s, 3H), 7.34 (t, J = 8.0 Hz, 1H), 7.44-7.50 (m, (m, 2H), 7.66-7.72 (m, 1H), 8.00-8.09 (m, 4H), 8.19 (d, J= 7.6
1H), 7.62 (t, J = 7.6 Hz, 2H), 7.66-7.72 (m, 1H), 8.00-8.06 (m, Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.4, 52.4, 127.2, 129.3,
3H), 8.14 (t, J = 1.6 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 44.4, 129.4, 129.8, 133.1, 134.1, 138.7, 139.5, 166.7, 173.4; FTIR
127.2, 127.6, 129.4, 129.6, 129.8, 132.1, 134.0, 134.2, 137.5, (KBr) 732, 820, 983, 1139, 1221, 1278, 1447, 1572, 1630, 1719,
138.7, 172.9; FTIR (KBr) 748, 980, 1146, 1221, 1565, 1627, 2929, 3019 cm-1; MS (m/z): [M]+ 317.00.
2927, 3022 cm-1; MS (m/z): [M]+ 292.85.
N-(2-Hydroxybenzoyl)-S-methyl-S-phenylsulfoximine (3p):21
N-(2-Bromobenzoyl)-S-methyl-S-phenylsulfoximine (3j):21
Yield 61%; 83 mg; brown viscous liquid; Rf 0.41 (40% ethyl
Yield 79%; 113 mg; white solid; mp 89-91 C [lit. 89-91 C];21 acetate in hexanes); H NMR (CDCl3, 400 MHz) δ 3.47 (s, 3H),
Rf 0.30 (30% ethyl acetate in hexanes); H NMR (CDCl3, 400 6.82-6.89 (m, 1H), 6.92 (dd, J = 8.4, 1.2 Hz, 1H), 7.36-7.44 (m,
o
o
1
1
MHz) δ 3.49 (s, 3H), 7.24 (td, J = 7.6, 1.6 Hz, 1H), 7.33 (td, J = 1H), 7.60-7.68 (m, 2H), 7.72 (tt, J = 7.6, 1.6 Hz, 1H), 8.01-8.07
7.6, 1.6 Hz, 1H), 7.58-7.66 (m, 3H), 7.67-7.73 (m, 1H), 7.80 (dd, (m, 2H), 8.09 (dd, J = 8.0, 1.6 Hz, 1H), 11.84 (br s, 1H); 13C NMR
J = 7.6, 1.6 Hz, 1H), 8.08-8.14 (m, 2H); 13C NMR (CDCl3, 100 (CDCl3, 100 MHz) δ 44.9, 117.5, 117.6, 118.7, 127.2, 130.0,
MHz) δ 44.3, 120.4, 127.2, 127.4, 129.8, 130.7, 131.3, 133.8, 131.2, 134.3, 135.1, 138.5, 162.2, 178.3; FTIR (Neat) 759, 982,
134.1, 138.5, 175.1; FTIR (KBr) 743, 981, 1146, 1220, 1447, 1159, 1223, 1340, 1482, 1590, 1627, 2928, 3020, 3449 cm-1;
1584, 1633, 2924, 3061 cm-1.
MS (m/z): [M]+ 275.00.
N-(4-Cyanobenzoyl)-S-methyl-S-phenylsulfoximine (3k):21
N-(1-Naphthoyl)-S-methyl-S-phenylsulfoximine (3q):21
Yield 81%; 115 mg; white solid; mp 81-83 oC [lit. 78-80 oC];21 Rf Yield 94%; 145 mg; colourless viscous liquid; Rf 0.34 (30%
1
1
0.22 (30% ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ 3.44 (s,
δ 3.48 (s, 3H), 7.60-7.66 (m, 2H), 7.67-7.74 (m, 3H), 8.01-8.06 3H), 7.45-7.59 (m, 5H), 7.63 (tt, J = 7.2, 1.2 Hz, 1H), 7.81-7.86
(m, 2H), 8.24 (d, J = 8.4 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ (m, 1H), 7.95 (d, J = 8.0 Hz, 1H), 8.03-8.08 (m, 2H), 8.36 (dd, J =
44.3, 115.3, 118.5, 127.1, 129.8, 129.9, 131.9, 134.2, 138.3, 7.2, 1.2 Hz, 1H), 9.01 (d, J = 8.4 Hz, 1H); 13C NMR (CDCl3, 100
139.5, 172.3; FTIR (KBr) 739, 839, 983, 1136, 1283, 1447, 1561, MHz) δ 44.4, 124.5, 125.9, 126.4, 127.1, 127.2, 128.3, 129.7,
1629, 2926, 3019 cm-1; MS (m/z): [M]+ 284.15.
129.8, 131.3, 132.3, 132.8, 133.8, 133.9, 138.7, 176.5; FTIR
N-(4-Trifluorobenzoyl)-S-methyl-S-phenylsulfoximine (3l):21
(KBr) 731, 973, 1146, 1297, 1509, 1586, 1625, 2930, 3055 cm-
o
1
Yield 82%; 134 mg; white solid; mp 105-107 C [lit. 102-104
.
oC];21 Rf 0.40 (30% ethyl acetate in hexanes); H NMR (CDCl3, N-(Thiophene-2-carbonyl)-S-methyl-S-phenylsulfoximine (3r):
1
o
400 MHz) δ 3.47 (s, 3H), 7.58-7.67 (m, 4H), 7.69 (tt, J = 7.2, 1.6 Yield 79%; 104 mg; white solid; mp 116-118 C; Rf 0.45 (40%
Hz, 1H), 8.00-8.07 (m, 2H), 8.26 (d, J = 8.4 Hz, 2H); 13C NMR ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ 3.45 (s,
1
(CDCl3, 100 MHz) δ 44.4, 124.0 (q, J = 271.0 Hz), 125.1(q, JC-F
=
3H), 7.06 (dd, J = 4.8, 3.6 Hz, 1H), 7.48 (dd, J = 5.2, 1.2 Hz, 1H),
3.0 Hz), 127.2, 129.8, 133.6 (q, JC-F = 32.0 Hz), 134.2, 138.6, 7.57-7.64 (m, 2H), 7.68 (tt, J = 7.2, 1.6 Hz, 1H), 7.79 (dd, J = 3.6,
138.8, 173.0; 19F NMR (CDCl3, 470 MHz) δ -66.0; FTIR (KBr) 1.2 Hz, 1H), 8.01-8.07 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ
737, 863, 979, 1174, 1283, 1320, 1449, 1580, 1629, 2923, 3058 44.5, 127.3, 127.8, 129.8, 131.7, 132.2, 134.0, 141.2, 169.0;
cm-1; MS (m/z): 327.05.
FTIR (KBr) 735, 975, 1119, 1219, 1273, 1518, 1609, 2919, 3079
N-(4-Nitrobenzoyl)-S-methyl-S-phenylsulfoximine (3m):21
cm-1; HRMS (m/z): [M+H]+ calcd. for C12H12NO2S2: 266.0309;
Yield 87%; 132 mg; pale yellow solid; mp 128-130 oC [lit. 126- found: 266.0291.
128 oC];21 Rf 0.48 (40% ethyl acetate in hexanes); 1H NMR N,N-(Terephthaloyl)bis(S-methyl-S-phenylsulfoximine) (3s):
o
(CDCl3, 400 MHz) δ 3.50 (s, 3H), 7.61-7.67 (m, 2H), 7.72 (tt, J= Yield 88%; 194 mg; white solid; mp 190-192 C; Rf 0.31 (60%
1
7.2, 1.2 Hz, 1H), 8.02-8.07 (m, 2H), 8.21-8.26 (m, 2H), 8.28-8.32 ethyl acetate in hexanes); H NMR (DMSO-d6, 400 MHz) δ 3.65
(m, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.5, 123.3, 127.2, 130.0, (s, 6H), 7.68-7.74 (m, 4H), 7.75-7.85 (m, 3H), 8.03-8.10 (m, 7H);
130.5, 134.4, 138.4, 141.1, 150.1, 172.2; FTIR (KBr) 720, 830, 13C NMR (DMSO-d6, 100 MHz) δ 41.4, 125.3, 126.9, 127.8,
978, 1275, 1347, 1521, 1599, 1632, 2855, 2925 cm-1; MS (m/z): 132.0, 136.7, 136.8, 170.3; FTIR (KBr) 733, 969, 1132, 1211,
[M]+ 304.05.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
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1267, 1446, 1601, 2920, 3020 cm-1; HRMS (m/z): [M+H]+ calcd. 980, 1143, 1282, 1502, 1629, 2935, 3020 cm-1; MS (m/z): [M]+
View Article Online
DOI: 10.1039/C6RA21732J
for C22H21N2O4S2: 441.0943; found: 441.0971.
311.05.
N-(4-Methylbenzoyl)-S-methyl-S-(4-methoxyphenyl)
N-(4-Methylbenzoyl)-S-methyl-S-(4-chlorophenyl)sulfoximine
sulfoximine (3t):21 Yield 91%; 138 mg; white solid; mp 106-108 (3z): 21 Yield 86%; 132 mg; white solid; mp 118-120 oC [lit. 122-
o
o
1
oC [lit. 111-113 C];21 Rf 0.42 (40% ethyl acetate in hexanes); 124 C];21 Rf 0.41 (30% ethyl acetate in hexanes); H NMR
1H NMR (CDCl3, 400 MHz) δ δ 2.38 (s, 3H), 3.43 (s, 3H), 3.86 (s, (CDCl3, 400 MHz) δ 2.40 (s, 3H), 3.44 (s, 3H), 7.21 (d, J = 8.0 Hz,
3H), 7.04-7.07 (m, 2H), 7.20 (d, J = 8.0 Hz, 2H), 7.93-8.00 (m, 2H), 7.57 (d, J = 8.8 Hz, 2H), 7.97 (d, J = 8.8 Hz, 2H), 8.03 (d, J =
2H), 8.05 (d, J = 8.0 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 21.7, 8.0 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 21.7, 44.5, 128.8,
44.8, 55.8, 115.0, 128.8, 129.4, 129.5, 130.2, 133.2, 142.6, 128.9, 129.6, 130.1, 132.8, 137.7, 140.7, 143.0, 174.3; FTIR
163.9, 174.3; FTIR (KBr) 831, 982, 1139, 1282, 1593, 1624, (KBr) 829, 984, 1136, 1222, 1573, 1625, 2925, 3022 cm-1; MS
2929, 3019 cm-1.
(m/z): [M]+ 306.85.
N-Benzoyl-S-methyl-S-(4-bromophenyl)sulfoximine (3u): Yield N-(4-Methoxybenzoyl)-S-methyl-S-(4-chlorophenyl)
o
89%; 150 mg; white solid; mp 102-104 C; Rf 0.54 (30% ethyl sulfoximine (3aa): Yield 80%; 129 mg; pale white solid; mp
1
o
1
acetate in hexanes); H NMR (CDCl3, 400 MHz) 3.45 (s, 3H), 106-108 C; Rf 0.36 (40% ethyl acetate in hexanes); H NMR
7.38-7.44 (m, 2H), 7.52 (tt, J = 7.6, 1.6 Hz, 1H), 7.75 (d, J = 8.4 (CDCl3, 400 MHz) δ 3.43 (s, 3H), 3.85 (s, 3H), 6.89 (d, J = 8.8 Hz,
2H), 7.91 (d, J = 8.4 Hz, 2H), 8.11-8.16 (m, 2H); 13C NMR (CDCl3, 2H), 7.57 (d, J = 8.8 Hz, 2H), 7.97 (d, J = 8.8 Hz, 2H), 8.10 (d, J =
100 MHz) δ 44.5, 128.2, 128.9, 129.3, 129.6, 132.5, 133.1, 8.8 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.6, 55.5, 113.4,
135.4, 138.2, 174.3; FTIR (KBr) 712, 821, 981, 1135, 1281, 128.1, 128.8, 130.1, 131.6, 137.9, 140.6, 163.1, 173.8; FTIR
1571, 1628, 2925, 3020 cm-1; MS (m/z): [M]+ 336.75, [M+2]+ (KBr) 814, 973, 1131, 1252, 1467, 1610, 2959, 3016 cm-1; MS
338.75.
(m/z): [M]+ 322.95.
N-(3-Methoxybenzoyl)-S-methyl-S-(4-bromophenyl)
sulfoximine (3v): Yield 85%; 156 mg; white solid; mp 98-100 Yield 81%; 116 mg; pale yellow solid, mp 122-124 C [lit. 127-
N-(4-Methylbenzoyl)-S-ethyl-S-phenylsulfoximine (3ab):21
o
oC; Rf 0.45 (30% ethyl acetate in hexanes); 1H NMR (CDCl3, 400 129 C];21 Rf 0.40 (30% ethyl acetate in hexanes); H NMR
MHz) δ 3.43 (s, 3H), 3.83 (s, 3H), 7.06 (d, J = 8.0 Hz, 1H), 7.31 (t, (CDCl3, 400 MHz) δ 1.29 (t, J = 7.2 Hz, 3H), 2.39 (s, 3H), 3.59 (q,
J = 7.6 Hz, 1H), 7.66 (s, 1H), 7.73-7.78 (m, 3H), 7.89 (d, J = 8.0 J = 7.2 Hz, 2H), 7.21 (d, J = 7.6 Hz, 2H), 7.56-7.61 (m, 2H); 7.66
Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.4, 55.5, 113.8, 118.9, (tt, J = 7.6, 1.2 Hz, 1H), 7.96-8.01 (m, 2H); 8.07 (d, J = 8.4 Hz,
122.1, 128.8, 129.1, 129.2, 133.1, 126.8, 138.1, 159.5, 174.0; 2H); 13C NMR (CDCl3, 100 MHz) δ 7.4, 21.7, 50.7, 128.1, 128.8,
FTIR (KBr) 759, 803, 983, 1118, 1222, 1286, 1579, 1627, 2927, 129.6, 129.7, 133.2, 133.8, 136.8, 142.7, 174.3; FTIR (KBr) 755,
o
1
3014 cm-1.
836, 929, 1173, 1283, 1446, 1571, 1625, 2977, 3060 cm-1; MS
N-(4-Chlorobenzoyl)-S-methyl-S-(4-bromophenyl)sulfoximine
(3w): Yield 73%; 136 mg; white solid; mp 116-118 C; Rf 0.57
(30% ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ
3.44 (s, 3H), 7.37 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 8.4 Hz, 2H),
7.89 (d, J = 8.4 Hz, 2H), 8.07 (d, J = 8.4 Hz, 2H); 13C NMR (CDCl3,
100 MHz) δ 44.5, 128.5, 128.8, 129.5, 131.0, 133.2, 133.9,
138.0, 138.8, 173.3; FTIR (KBr) 819, 978, 1136, 1215, 1281,
1567, 1622, 2922, 3010 cm-1; MS (m/z): [M]+ 370.35, [M+2]+
372.20.
(m/z): [M]+ 286.65.
o
1
Acknowledgements
We thank the DST New Delhi (Project SB/S1/OC-72/2013) for
financial support. BDB thanks SERB (N-PDF), New Delhi for
fellowship and NS thanks CSIR, New Delhi for senior research
fellowship.
N-(1-Naphthoyl)-S-methyl-S-(4-bromophenyl)sulfoximine
(3x): Yield 93%; 180 mg; colourless viscous liquid; Rf 0.54 (30%
ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ 3.43 (s,
3H), 7.44-7.57 (m, 3H), 7.71 (d, J = 8.8 Hz, 2H), 7.83-7.87 (m,
1H), 7.90 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 8.4 Hz, 1H), 8.34 (dd, J
= 7.2, 1.6 Hz, 1H), 8.96-9.02 (m, 1H); 13C NMR (CDCl3, 100 MHz)
δ 44.4, 124.5, 126.0, 126.4, 127.4, 128.4, 128.8, 129.2, 130.1,
131.4, 132.5, 132.6, 133.1, 133.9, 138.0, 176.4; FTIR (Neat)
782, 820, 973, 1147, 1220, 1246, 1571, 1630, 2927, 3054 cm-1;
MS (m/z): [M]+ 386.70, [M+2]+ 388.95.
Notes and references
1
1
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N-(4-Fluorobenzoyl)-S-methyl-S-(4-chlorophenyl)sulfoximine
(3y): Yield 80%; 124 mg; white solid; mp 86-88 oC; Rf 0.52 (30%
3530-3534.
(a) X.-F. Wu, H. Neumann and M. Beller, ChemSusChem,
1
ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz) δ 3.44 (s,
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3H), 7.02-7.11 (m, 2H), 7.58 (d, J = 8.8 Hz, 2H), 7.97 (d, J = 8.8
Hz, 2H), 8.10-8.18 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 44.5,
115.2 (d, JC-F = 21.0 Hz), 128.8, 130.2, 131.7 (d, JC-F = 3.0 Hz),
132.0 (d, JC-F = 9.0 Hz), 137.5, 140.8, 165.6 (d, JC-F = 251.0 Hz),
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DOI: 10.1039/C6RA21732J
Heterogeneous Pd/C catalyzed three component protocol is developed for the
sulfoximinocarbonylation of aryl halides.