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92 2 Transformation of Sulfoximines and Cyclic Sulfoximines
R
O
N
S
O
[RuCl
2
(pcymene)]
2
(10 mol %)
R
O
N
S
O
NHTs
+
TsN
3
35-88% yield
AgSbF
6
(40 mol %), KOAc
ClCH
2
CH
2
Cl
Scheme 2.43 Sulfoximine directed intermolecular O–C–H amidation of arenes with sulfonyl
azides
It has been reported that Ru(II) catalyzed the intermolecular ortho-C-H amidation
of arenes in N-benzoylated sulfoximines using sulfonyl azides with methylphenyl
sulfoximine as the directing group. The reaction proceeded according to a wide range
of substrates and was able to withstand any number of functional groups. According
to Scheme
2.43, the anthranilic acid derivatives were obtained through the basic
hydrolysis of the amidation product [
64].
The substrate scope of the sulfonyl azide-directed O–C–H amidation is broad,
encompassing various arenes as potential substrates. The regioselectivity of the reac-
tion is dictated by the position of the oxygen atom in the arene, allowing for the
selective activation of C–H bonds adjacent to this oxygen moiety. This regioselec-
tivity is a hallmark of the synthetic utility of this method, providing chemists with
a precise means to functionalize specific positions on arenes. The sulfonyl azide-
directed O–C–H amidation can be used in many different ways in chemistry. This
method makes it possible to directly add amide functions to complex molecules,
which makes it easier to make compounds that are useful in medicine and molecules
that have biological effects. Being able to selectively functionalize arenes at certain
positions helps to make molecular structures more diverse and speeds up the process
of synthesizing target compounds.
The synthetic applications of the sulfonyl azide-directed O–C–H amidation are
multifaceted. This method enables the direct incorporation of amide functionali-
ties into complex molecules, facilitating the synthesis of pharmaceutically relevant
compounds and bioactive molecules. The ability to selectively functionalize arenes
at specific positions contributes to the diversification of molecular structures and
streamlines the synthetic route to target compounds.
A look at other methods of C–H functionalization: This sulfonyl azide-directed
amidation method is one of the best for adding C–H groups because it is selective
and sulfonyl azides can be used in a lot of different ways as directing groups. There
are other ways to do this, like using directed ortho-metalation or directing groups
with nitrogen functionality. However, the sulfonyl azide-directed method has its own
benefits, such as a milder reaction environment and the chance to make a wide range
of amide products.
It is very important to understand the detailed mechanisms of the sulfonyl azide-
directed amidation in order to move the field forward. Studies that look at how things
work can help us understand the important building blocks, reaction pathways, and
factors that control regioselectivity. It is also possible to make the transformation even
more efficient, selective, and long-lasting by designing new catalysts and ligands.
2.1 Transformation of Sulfoximines into Sulfoximine Derivatives 93
The sulfonyl azide-directed O–C–H amidation is an exciting area of research that
is always changing. Ongoing work focuses on broadening the range of substrates,
finding new directing groups, and looking into how they can be used in the production
of natural products and drugs. As the sulfonyl azide-directed approach is further
integrated into various synthetic methods, it is expected to open up new synthetic
opportunities.
Subsequently, the sulfonyl azide-directed intermolecular O–C–H amidation of
arenes is a revolutionary way to make chemicals that uses the directing power of
sulfonyl azides to selectively activate C–H groups. This method makes it easy and
quick to add amide functionalities to arenes, which speeds up the synthetic process
and makes arene substrates more useful. The interaction between sulfonyl azides and
transition metal catalysts allows for a precise and selective change. This method is
useful in modern organic synthesis. The sulfonyl azide-directed amidation is expected
to make it easier to make complex molecules, which could have uses in medicinal
chemistry, materials science, and other fields.
2.1.13 Synthesis of EP3 Receptor Antagonist Analogue
from N-aroyl Sulfoximines Using Heck-Type Reaction
The synthesis of an EP3 receptor antagonist analogue from N-aroyl sulfoximines via
a Heck-type reaction showcases an innovative and strategic approach in medicinal
chemistry. The utilization of transition metal-catalyzed Heck-type reactions for the
construction of biologically relevant molecules is a powerful method that allows for
the efficient introduction of diverse functionalities into organic frameworks. In order
to make the EP3 receptor antagonist analogue, structural elements were used that
are known to bind and work against the EP3 receptor. The Heck-type reaction is a
key step in adding certain aryl functions that are similar to important parts of known
EP3 receptor antagonists.
To make it possible for Ru(II) to selectively and chemically alkenylate aromatics
and heteroaromatics with acrylic acids, α,β-unsaturated ketones, or vinyl sulfones,
Sahoo et al. created a sulfadiazine targeting group [
65]. Isoquinolinones were
produced by cyclizing N-aroyl sulfoximines with diphenylacetylenes, as shown in
Scheme
2.44. The synthesis of EP3 receptor antagonistic resemblance has been
achieved with the use of this method, with excellent results.
Furthermore, the Heck-type reaction is employed as the central synthetic trans-
formation in the route. This palladium-catalyzed coupling between the aryl halide
derived from N-aroyl sulfoximines and an olefinic partner allows for the controlled
construction of the carbon–carbon bond. The choice of olefin partner is critical, as it
determines the nature of the aryl substitution and contributes to the overall structure
of the EP3 receptor antagonist analogue. To get high yields, regioselectivity, and
the stereochemistry you want, you have to make sure the Heck-type reaction condi-
tions are just right. Fine-tuning the reaction parameters, like the palladium source,
94 2 Transformation of Sulfoximines and Cyclic Sulfoximines
N
O
S
O
R
+
H
R
1
[RuCl
2
(p-cymene)]
2
(5 mol%)
AgBF
4
(20 mol%)
N
O
S
O
R
R
1
Cu(OAc)
2
•H
2
O (1 equiv)
ClCH
2
CH
2
Cl
[RuCl
2
(p-cymene)]
2
(5 mol%)
AgBF
4
(20 mol%)
Cu(OAc)
2
•H
2
O, 1,4-Dioxane, 120
o
C
Ph
Ph
NH
O
R
Ph
Ph
EP3 receptor
Scheme 2.44 Synthesis of EP3 receptor antagonist analogue
ligands, solvent, and temperature, makes sure that the coupling process works and
keeps side reactions to a minimum. The Heck reaction makes it possible to add
pharmacophoric groups precisely to the sulfoximine scaffold. These groups were
carefully chosen because of how they are known to interact with the EP3 receptor
and what role they play in giving compounds antagonist properties. You can change
the regiochemistry of the Heck reaction to put these pharmacophores in a way that
makes them easier for receptors to bind to them.
The Heck reaction can create stereoisomers, and the stereochemistry at the newly
formed carbon–carbon bond is very important for the EP3 receptor antagonist
analogue’s biological activity. The stereochemical outcome of the reaction depends
on how well the ligands on the palladium catalyst are thought out and how the
olefinic partner is shaped. After the Heck-type reaction, the synthesized EP3 receptor
antagonist analogue may go through more changes to make its pharmacokinetic and
physicochemical properties better. More steps of functionalization, like oxidation,
reduction, or derivatization of functional groups, help to fine-tune the analogue so
that it has better drug-like properties and biological activity.
The synthesized EP3 receptor antagonist analogue is checked using different
analytical techniques, such as NMR spectroscopy, mass spectrometry, and chro-
matographic methods. These methods confirm the analogue’s identity, purity, and
structural integrity, which is important information for further biological tests. The
EP3 receptor antagonist analogue goes through strict biological evaluations to see
how well it binds, how selectively it binds, and how well it works against the EP3
receptor. In vitro tests and, possibly, in vivo studies help us learn more about the
analogue’s pharmacological profile and how it might work as a medicine. The synthe-
sized analogue can be used in a larger structure–activity relationship (SAR) study,
in which systematic changes in its structure are looked at to find out how different
structural motifs affect the ability of EP3 receptors to bind and block. The SAR
studies help improve the analogue’s effectiveness even more.
In summary, the synthesis of an EP3 receptor antagonist analogue from N-aroyl
sulfoximines via a Heck-type reaction is a well-designed and strategically executed
approach. The incorporation of key pharmacophores through a controlled Heck
2.1 Transformation of Sulfoximines into Sulfoximine Derivatives 95
coupling not only streamlines the synthetic route but also allows for the introduc-
tion of diverse functionalities critical for receptor binding and antagonist activity.
This methodology contributes to the synthesis of novel drug candidates with poten-
tial therapeutic applications in conditions where modulation of the EP3 receptor is
desirable.
2.1.14 Sulfoximines Undergo Halogenation
at the β-C(sp
3
)-H Bond
Overview of β-C(sp
3
)-H Halogenation refers to the chemical process of introducing a
halogen element into a compound. The process of halogenation of β-C(sp
3
)-H bonds
in sulfoximines entails the specific breaking of hydrogen atoms located next to the
sulfur–nitrogen double bond. This transformation is of strategic importance as it
enables the precise incorporation of halogen substituents, such as fluorine, chlorine,
bromine, or iodine, at specific locations within the molecular structure. This process
benefits from the utilization of transition metal catalysts, which significantly improve
both its efficiency and selectivity. The process of halogenating β-C(sp
3
)-H bonds in
sulfoximines is a highly valuable and important chemical reaction. It provides a
versatile approach for incorporating halogen substituents at specific locations within
complex molecular structures. Catalyzed by transition metals, this process allows for
the targeted modification of C–H bonds that are adjacent to the sulfoximine group.
As a result, a wide range of halogenated sulfoximine derivatives can be obtained,
which have significant applications in medicinal chemistry, materials science, and
agrochemical research.
Transition metal catalysts are crucial in facilitating the halogenation of β-C(sp
3
)-
H bonds in sulfoximines. Palladium, rhodium, or copper complexes, often with
suitable ligands, act as catalysts to selectively activate C–H bonds that are adja-
cent to the sulfoximine functional group. These catalysts serve as a foundation
for precise and effective halogenation reactions. Gaining a thorough understanding
of the underlying mechanisms involved in the β-C(sp
3
)-H halogenation process is
essential for improving reaction conditions and developing highly effective catalytic
systems. The reaction generally entails the utilization of a metal catalyst to activate
C–H bonds, followed by halogenation and subsequent regeneration of the catalyst.
In-depth mechanistic investigations provide valuable understanding of the factors
that affect selectivity, regiochemistry, and the overall efficiency of the halogenation
reaction.
Pd(II)-catalyzed bromination and chlorination of the 1°-β-C (sp
3
-)-H bond of N-
MPyS propionamides using N-Br/Cl-phthalimides as halogenated agents, as shown
in Scheme
2.45). This was carried out through the use of the S-methyl-S-2-pyridyl-
sulfoximine (MPyS) group as the catalyst [
66
]. You can make highly functionalized
α-trisubstituted aliphatic acid derivatives by adding halogens and acetoxyl groups to
α-dimethyl MPyS-N-amide one step at a time.
96 2 Transformation of Sulfoximines and Cyclic Sulfoximines
N
O
S
O
N
+
Pd(OAc)
2
(10 mol%)
AcOH (2.5 equiv)
N
O
S
O
N
Br
R
2
R
1
H
R
2
R
1
N
O
O
Br
DCE, 60-65
o
C. 15 h
Scheme 2.45 MPyS-directed bromination, chlorination of β-C(sp
3
)-H of N-MPyS propionamides
One of the key features of β-C(sp
3
)-H halogenation in sulfoximines is the regios-
electivity of the process. The proximity of the sulfoximine moiety influences the site
selectivity of C–H activation. The regioselective installation of halogen substituents
at specific positions adjacent to the sulfoximine allows for the controlled manip-
ulation of molecular architecture. The range of β-C(sp
3
)-H halogenation in sulfox-
imines is extensive, including a variety of substrates with different functional groups.
Nevertheless, the effectiveness of the method may be restricted based on the charac-
teristics of the material being worked on and its ability to work well with the selected
catalyst made from a transition metal. Challenging substrates often necessitate the
optimization of reaction conditions.
The process of introducing halogen atoms into β-C(sp
3
)-H bonds in sulfoximines
provides opportunities for a wide range of practical uses in synthetic chemistry.
The addition of halogen substituents increases the range of functions that sulfox-
imines can perform, enabling subsequent reactions such as cross-coupling reactions,
cyclizations, or additional functionalizations. These halogenated sulfoximines are
useful intermediates in the synthesis of bioactive compounds and complex molec-
ular structures. The capacity to specifically introduce halogen atoms into β-C(sp
3
)-H
bonds in sulfoximines is especially significant in the field of medicinal chemistry.
Pharmaceuticals often contain halogen substituents, which have a significant impact
on properties such as bioavailability and binding affinity. By employing this method,
the deliberate integration of halogens enables precise adjustment of molecular char-
acteristics, thereby potentially augmenting the biological efficacy of synthesized
compounds. Also, halogenated sulfoximines acquired via β-C(sp
3
)-H halogenation
can be utilized as valuable precursors in cross-coupling reactions. The utilization
of palladium-catalyzed coupling in conjunction with organometallic reagents allows
for the incorporation of a wide range of functional groups, thereby broadening the
scope of synthetic opportunities and facilitating the creation of intricate molecular
structures.
Additionally, the ability to selectively modify specific β-C(sp
3
)-H bonds in sulfox-
imines provides a clear advantage in designing synthetic strategies. The close prox-
imity to the sulfoximine moiety enables accurate regulation of halogenation place-
ment, offering synthetic chemists a potent means for strategically modifying intricate
molecules.
The latest developments in transition metal-catalyzed C–H activation techniques
have greatly broadened the range of options for β-C(sp
3
)-H halogenation in sulfox-
imines. The utilization of earth-abundant metals, novel ligands, and inventive reaction
conditions plays a significant role in advancing the development of catalytic systems
2.1 Transformation of Sulfoximines into Sulfoximine Derivatives 97
that are both more sustainable and efficient. Chiral sulfoximines are typically synthe-
sized through halogenation, which requires enantiopure starting materials or chiral
auxiliaries. It is crucial to have the capability to selectively add halogen atoms to
specific carbon-hydrogen (C-H) bonds in chiral sulfoximines without affecting their
stereochemistry. This is necessary for creating enantiopure halogenated compounds,
which are important for producing advanced intermediates used in asymmetric
synthesis.
Ongoing research in the field of β-C(sp
3
)-H halogenation in sulfoximines is
focused on expanding the range of substances that can be used, improving the effec-
tiveness of catalysts, and investigating new methods of halogenation. Possible future
directions may entail the advancement of catalytic systems that are more environ-
mentally friendly and the utilization of this approach for synthesizing intricate natural
products and materials with customized characteristics.
2.1.15 Sulfoximine as Ligand for Asymmetric Catalysis
Sulfoximines have become notable and efficient ligands in asymmetric catalysis,
serving as a crucial element in the advancement of catalytic techniques that facilitate
the production of compounds with high enantiomeric purity. Sulfoximines possess
distinctive electronic and steric characteristics that make them highly adaptable
ligands. Their effective utilization in asymmetric catalysis has attracted consider-
able interest in the realm of synthetic chemistry. Chiral sulfoximines as ligands with
chiral properties; Chirality is crucial in numerous biological processes and serves as
a critical aspect in the development of pharmaceuticals and agrochemicals. Chiral
sulfoximines, which can be obtained from easily accessible starting materials, func-
tion as chiral ligands that confer chirality to transition metal catalysts. The chiral
complexes that are formed demonstrate significant catalytic activity and selectivity
in various asymmetric transformations.
Chiral sulfoximines have been utilized in various metal-catalyzed reactions,
such as asymmetric hydrogenation, asymmetric allylic substitution, and asymmetric
cycloadditions. These catalytic systems facilitate the effective production of chiral
compounds with a high degree of enantiomeric purity, rendering them highly useful
in the synthesis of pharmaceutical intermediates and natural products.
In the year 2004, Bolm made the discovery that benzene-bridged aminobenzyl-
substituted sulfoximines have the potential to function as useful ligands for the forma-
tion of C–C bonds [
67
]. According to Scheme
2.46, this ligand has the potential to
be used in the copper-catalyzed enantioselective Mukaiyama-type aldol reaction.
In 2005, Bolm and his colleagues made N–Phosphino sulfoximines from BINOL
for the first time and tested them as a ligand in asymmetric catalysis. As shown
in Scheme
2.47, it works very well in Rh-catalyzed asymmetric hydrogenation of
functionalized olefins and in Pd-catalyzed allyllic alkylation [
68].
Furthermore, sulfoximines have the ability to bind to transition metal centers,
resulting in the formation of stable complexes. These complexes act as catalysts in
98 2 Transformation of Sulfoximines and Cyclic Sulfoximines
Synthesis of ligand:
Br
NO
2
+
S
O
HN
Ph
Pd(OAc)
2
, BINAP
Cs
2
CO
3
, C
7
H
8
,
73-95 %
NO
2
S
O
N
Ph
Fe, AcOH
EtOH, H
2
O,
74-87 %
NH
2
S
O
N
Ph
RCHO
NaBH
3
CN or NaBH
4
MeOH, AcOH, r.t.
81-85 %
HN
S
O
N
Ph
R
Catalysis with sulfoximine ligand:
OBn
O
O
+
OSiMe
3
Cu(OTf)
2
(10 mol%)
ligand (10 mol%)
THF, additive
-40
o
C, 48h
OBn
O
O
OH
91% ee
sulfoximine ligand
Scheme 2.46 C1-symmetric sulfoximines as ligands in copper-catalyzed asymmetric mukaiyama-
type aldol reactions
O
O
PCl
+
SR
1
O
NH
R
2
Et
3
N, toluene
-78
o
C to rt
O
O
P
S
R
1
O
N
R
2
a
: R
BINOL
/S
Sulf
; R = Ph, R' = Me
b
: S
BINOL
/S
Sulf
; R = Ph, R' = Me
c
: R
BINOL
/S
Sulf
; R = Ph, R' = t-Bu
d
: S
BINOL
/S
Sulf
; R = Ph, R' = t-Bu
e
: R
BINOL
; R = R' = Me
f
: R
BINOL
; R = R' = Ph
Synthesis of BINOL-sulfoximine ligands:
Catalysis with sulfoximine ligands
CO
2
CH
3
CO
2
CH
3
[Rh(cod)
2
]BF
4
ligand
cod = 1,5-cyclooctadiene
CH
2
Cl
2
, 1.3bar H
2
, rt, 20 h
CO
2
CH
3
CO
2
CH
3
ligand
a
b
e
f
Configuration
of product:
R
S
R
R
% ee
99
99
99
98
CO
2
CH
3
NHAc
[Rh(cod)
2
]BF
4
ligand
CH
2
Cl
2
, 1.3bar H
2
, rt, 20 h
CO
2
CH
3
NHAc
ligand
a
b
e
f
Configuration
of product:
S
R
S
S
% ee
98.8
98
98.2
98.2
Scheme 2.47 BINOL-derived N–Phosphino sulfoximines as ligands for asymmetric catalysis
2.1 Transformation of Sulfoximines into Sulfoximine Derivatives 99
asymmetric reactions. The utilization of sulfoximine ligands in coordination chem-
istry enables precise manipulation of the alignment of reacting substrates, thereby
exerting a significant influence on the stereochemical result of the catalytic process.
Steric and electronic effects: The substituents on the sulfoximine scaffold can be
customized to bestow distinct steric and electronic characteristics to the ligand.
The ability to adjust this characteristic is essential for precisely adjusting the cata-
lyst’s responsiveness and specificity in asymmetric transformations. Sulfoximines
are highly versatile ligands due to their distinctive combination of steric bulk and
electronic effects.
Asymmetric hydrogenation: In asymmetric hydrogenation, sulfoximines act as
chiral ligands coordinating to transition metal catalysts, facilitating the selective
reduction of prochiral substrates. The resulting chiral sulfoximine-metal complexes
demonstrate high enantioselectivity, making this class of ligands particularly useful in
the synthesis of chiral amines. Asymmetric Allylic Substitution: Sulfoximines have
been used as ligands in reactions involving the substitution of allylic compounds
with high selectivity. The binding of chiral sulfoximines to metal catalysts improves
the selectivity of allylic substitution reactions, enabling the precise creation of
chiral carbon–carbon bonds. Asymmetric cycloadditions: Sulfoximines contribute
to the success of asymmetric cycloadditions by serving as efficient ligands in metal-
catalyzed processes. These reactions lead to the formation of complex cyclic struc-
tures with high levels of enantiocontrol, showcasing the utility of sulfoximines in
diverse synthetic applications. Moreover, enantioselective C–H functionalization:
Recent developments have highlighted the role of sulfoximines in enantioselective
C–H functionalization reactions. These transformations, often catalyzed by transi-
tion metals, provide direct and efficient routes to chiral molecules, and sulfoximine
ligands contribute to controlling the stereochemistry of the formed products.
The effectiveness of sulfoximines as ligands in asymmetric catalysis can be
attributed not only to their ability to coordinate with other molecules, but also
to the distinct pathways they enable in chemical reactions. Investigating reaction
mechanisms offers valuable insights into the source of stereocontrol, which in turn
informs the development of enhanced catalytic systems. The utilization of sulfox-
imine ligands in asymmetric catalysis is continuously progressing, with ongoing
endeavors to broaden their applicability and improve their effectiveness. Scientists
are currently investigating new designs for ligands, refining the conditions under
which reactions occur, and uncovering innovative catalytic processes that utilize the
distinctive properties of sulfoximines.
To summarize, sulfoximines have successfully positioned themselves as adapt-
able and efficient ligands in the field of asymmetric catalysis. Sulfoximines are at
the forefront of modern synthetic methodology due to their ability to influence the
stereochemistry of diverse transformations and their tunable steric and electronic
properties. The use of sulfoximine ligands in asymmetric catalysis highlights their
importance in the development of efficient and selective methods for synthesizing
chiral molecules, with implications in multiple scientific fields.
100 2 Transformation of Sulfoximines and Cyclic Sulfoximines
2.2 Conversion of Sulfoximines into Other Compounds
Figuring out how sulfoximines might break down is very important for scientists
working with chemicals in agriculture and medicine. To break down sulfoximines
in the lab, different chemical changes happen, such as reduction and oxidation
routes and C–S bond cleavage reactions [
69]. Sulfoximines can go through a lot
of different synthetic changes, which gives chemists a lot of different ways to change
and function-enhance these useful building blocks. Sulfoximines are useful building
blocks in organic synthesis because they have a unique reactivity that lets them be
changed in specific ways. They do this by having a sulfur–nitrogen double bond
within the imine functional group.
2.2.1 Reduction to Thioethers
Sulfoximines are reduced to thioethers, which is a key step in the conversion process.
Usually, reducing agents like lithium aluminum hydride or other metal hydrides are
used for this transformation. When the sulfur atom in the sulfoximine moiety is
reduced, a sulfur–carbon bond forms, which changes the sulfoximine into a thioether.
Thioethers are used in many areas, such as medicinal chemistry and materials science.
2.2.2 Oxidation to Sulfoxides
Sulfoximines are reduced to thioethers, which is a key step in the conversion process.
Usually, reducing agents like lithium aluminum hydride or other metal hydrides are
used for this transformation. When the sulfur atom in the sulfoximine moiety is
reduced, a sulfur–carbon bond forms, which changes the sulfoximine into a thioether.
Thioethers are used in many areas, such as medicinal chemistry and materials science.
2.2.3 Cleavage to Amines
When sulfoximines are broken apart, they can be turned into amines. This is a very
important step in the process of making compounds that contain nitrogen. Some
nucleophiles, like amines or hydride sources, react with the sulfur–nitrogen bond in
sulfoximines. This breaks the S=N bond. Depending on the nucleophile that is used,
this process makes either a sulfide or an amine product.
2.2 Conversion of Sulfoximines into Other Compounds 101
2.2.4 N-Acylation
An acyl group can be added to the nitrogen atom during N-acylation of sulfoximines.
Arylating agents are often activated with coupling reagents or acid chlorides. This
makes it easier for amide bonds to form. This acylation method lets different acyl
groups be added, which increases the structural variety of sulfoximine derivatives.
2.2.5 N-Alkylation
In this process, alkyl groups are added to the nitrogen atom in sulfoximines. Alkyl
halides or other similar electrophiles are used to change this into another form.
N-alkylation is a powerful way to change the lipophilicity and steric properties of
sulfoximines, which can change how well they work in different situations.
2.2.6 The Formation of N-Heterocycles
Sulfoximines can help make N-heterocycles through cyclization reactions. Reac-
tions with the right reagents or conditions make it easier for a ring containing
the sulfoximine nitrogen to close. Using this method, different nitrogen-containing
heterocycles can be made, which could be useful in medicinal chemistry.
2.2.7 Transformation into Sulfinamides
Sulfoximines can be changed into sulfinamides by reacting with the right nucle-
ophiles. When the nucleophile hits the sulfur atom in the sulfoximine, the S=O bond
changes into a sulfinamide linkage. The motifs sulfinamides can be used in many
different ways, such as in medicinal chemistry and catalysis.
2.2.8 Formation of Nitriles
Sulfoximines can change into nitriles under certain reaction conditions. It is this
change that causes the S=N bond to break and a cyano group to form at the nitrogen
position. Functional groups called nitriles are very important and are used to make
many medicines and fine chemicals.