Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles

Article abstract of DOI:10.1002/chem.201805175

Aliphatic, aromatic, and heteroaromatic aldehydes were readily converted to corresponding nitriles in a one-pot reaction sequence with hydroxylamine and sulfuryl fluoride. The reaction proceeds at room temperature, does not require metal catalysts and special precautions, and produces nitriles in excellent yields. It is compatible with a variety of functional groups, can be performed in aqueous and organic solvents, and is readily scalable to multigram quantities. Mild conditions and high selectivity of the reaction enabled the construction of polyfunctional probes containing nitrile, alkyne, azide, and fluorosulfate groups for further orthogonal derivatization.

Full text of DOI:10.1002/chem.201805175

A Journal of
Accepted Article
Title: Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles
Authors: Jitendra Gurjar, Jorick Bater, and Valery V. Fokin
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of the final Version of Record (VoR). This work is currently citable by
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content of this Accepted Article.
To be cited as: Chem. Eur. J. 10.1002/chem.201805175
Link to VoR: http://dx.doi.org/10.1002/chem.201805175
Supported by

Chemistry - A European Journal
10.1002/chem.201805175
COMMUNICATION
Sulfuryl Fluoride Mediated Conversion of Aldehydes to Nitriles.
Jitendra Gurjar, Jorick Bater, and Valery V. Fokin*
Abstract: Aliphatic, aromatic, and heteroaromatic aldehydes are
readily converted to corresponding nitriles in a one-pot reaction
sequence with hydroxylamine and sulfuryl fluoride. The reaction
proceeds at room temperature, does not require metal catalysts and
special precautions, and produces nitriles in excellent yield. It is
compatible with a variety of functional groups, can be performed in
aqueous and organic solvents, and is readily scalable to multigram
quantities. Mild conditions and high selectivity of the reaction enable
construction of polyfunctional probes containing nitrile, alkyne, azide,
and fluorosulfate groups for further orthogonal derivatization.
Established methods for the preparation of aliphatic nitriles
take advantage of the highly nucleophilic character of the
cyanide anion. Aromatic nitriles are commonly prepared using
[
11]
[12]
the Sandmeyer
and the Rosenmund-von Braun reactions.
These syntheses require highly toxic metal cyanides, elevated
temperature, and introduce an additional carbon atom from the
cyanide nucleophile. Nitriles can also be obtained from
[
13–16]
[17,18]
[19–21]
[22–24]
alcohols,
amines,
amides,
and aldoximes.
However, these methods often require high temperature, metal
catalysts, and strong oxidizing reagents.
Dehydration of oximes is perhaps the most straightforward
[
25–28]
method of nitrile synthesis (eq. 1).
However, the use of high
Selective manipulation of functional groups in complex
molecules is an important goal of organic chemistry. Aldehydes
are versatile starting materials, ubiquitously available both from
natural and synthetic sources. They are used in oxidations,
reductions, and conversions to other functional groups, including
nitriles. The latter are found in pharmaceuticals, agrochemicals,
boiling solvents, acidic medium, high temperature and oxidizing
conditions limit the scope of these dehydrations and result in
[24]
side reactions.
The XtalFluor-E reagents reported by Paquin
[28]
offers a mild method for dehydration of oximes (eq. 2).
However, its high reactivity with primary amides and alcohols
makes it incompatible with these functionalities.
[
1],[2]
natural products, polymers, and materials.
A number of
nitrile-containing pharmacophores are present in enzyme
inhibitors and receptor ligands (Figure 1). Among those are
escitalopram (1), a selective serotonin reuptake inhibitor widely
Classic dehydration of aldoximes
OH
Harsh reaction conditions
Low functional group tolerance
Limited scope
N
dehydrating agent
R
CN
(1)
[
3]
R
H
Side reactions
used for the treatment of depression and anxiety; bicalutamide
2), an androgen receptor antagonist used as a therapy in
Recent developments
reagents and condions
(
[
4]
Expenxive reagents
Oxidizing conditions
Elevated temperature
Low functional group tolerance
O
advanced prostate cancer; milrinone (3), a phosphodiesterase
(2)
R
CN
[
5]
R
H
as shown below
inhibitor for the treatment of heart failure; fadrozole (4), a
selective non-steroidal aromatase inhibitor used for treatment of
[
6]
[7]
H
N
+
certain breast cancers; rilpivirine (5), for treatment of AIDS;
and nilvadipine (6), for the treatment of hypertension, cerebral
Me3Si
SiMe3
NH
2
OH•HCl
O
Ph
NHAc
O
N
S
[
8]
O
P
+
NH
O
Me
O
artery occlusion, and is under investigation for the treatment of
2
O
Ph
Ph
NH2
EtO
[
9]
O
N
S
Alzheimer’s disease.
Nitriles are also useful synthetic
+
+
N
F3C
TFA
cat. Bronsted acid
intermediates which can be converted to other functional groups,
including carboxylic acids, esters, amines, amides, amidines,
O
BF4
F
F
BF4
Nantz, 2012 Baily & Leadbeater, 2015 Paquin, 2015
Yu, 2015
Uchida, 2017
[
10]
and heterocycles.
This work
Inexpensive reagents
Mild conditions
Room temperature
Easily scalable
Broad scope
O
SO
2
F
2
, Et
3
N
(3)
CN
N
+
NH
2
OH•HCl
R
CN
OHH
N
R
H
CH
Cl , rt
O
O
O
CN
O
2
2
Me2N
S
CF3
CN
High selectivity
O
Me
N
H
F
Milrionone
3
Bicalutamide
F
2
Escitalopram
CN
Various nitrogen sources have been used for the synthesis of
1
NO2
O
CN
NH
[
29]
CN
nitriles
from
aldehydes.
Among
those
are
O-
N
Me
O
N
Me
Me
N
Me
O
OMe
CN
(diphenylphosphinyl)hydroxylamine (DPPH) reported by Nantz
HN
[30]
Me
N
H
and colleagues,
3
O-(4-CF -benzoyl)-hydroxylamine described
Fadrozole
N
Nilvadipine
[31]
[32]
4
by Yu, and O-protected oximes described by Uchida. A mild
oxidative conversion of aldehydes to nitriles in the presence of
an oxoammonium salt and hexamethyldisilazane (HMDS) was
Rilpivirine
6
5
Figure 1. Examples of nitrile containing pharmaceuticals.
[
33]
developed by Bailey and Leadbeater.
Recent oxidative
methods include aerobic copper-promoted cleavage of cyanide
[
34]
triple bond reported by You,
and iodine catalyzed oxidative
transformation of aldehydes to nitriles using ammonium acetate
Mr. J. Gurjar, Mr. J. Bater, Prof. Dr. V. V. Fokin
University of Southern California
and tert-butyl hydroperoxide (TBHP) as the oxidant reported by
[
35]
Shen.
The Bridge@USC and Loker Hydrocarbon Research Institute
002 Childs Way
We describe here a practical direct conversion of aldehydes
to nitriles which employs stable and readily available reagents
under mild conditions. The reaction does not require oxidizers,
proceeds rapidly and nearly quantitatively at ambient
temperature, and is compatible with various functional groups.
This one-pot transformation is accomplished by initial conversion
1
Los Angeles, CA 90089-3502, USA
E-mail: fokin@usc.edu
Supporting information for this article is given via a link at the end of
the document.
This article is protected by copyright. All rights reserved.

Chemistry - A European Journal
10.1002/chem.201805175
COMMUNICATION
of aldehydes to aldoximes by treatment with hydroxylamine,
which are then transformed to nitriles in situ upon reaction with
sulfuryl fluoride. The latter is a stable gas, produced on large
Thus, treatment of 4-bromobenzaldehyde with hydroxylamine
hydrochloride and triethylamine in water-ethanol (1:1) resulted in
93% conversion to 4-bromobenzonitrile 8d in 5 hrs.
[
36]
scale for use as an insecticide. In the laboratory setting, it has
been used for the synthesis of arylfluorosulfates and
Vial I
O
2 3 2 2
NH OH•HCl, Et N, CH Cl
Vial I
Vial II
R
CN
fluorosulfonates for the
sulfur(VI) fluoride
triflate surrogate in coupling
Likewise, hydroxylamine hydrochloride is a stable
exchange
R
H
Vial II
[
37,38]
7
8
chemistry,
and as
a
MSDI, KHF2, H2O, rt
[
39–43]
CN
reactions.
CN
CN
CN
O
CN
and inexpensive reagent in contrast to other hydroxylamine
MeO
O
N
[
44]
MeO
O
8
H
Br
derivatives such as O-mesitylsulfonylhydroxylamine (MSH)
a, 95%
8b, 99%
8c, 97%
[
45]
8d, 95%
CN
8
e, 93%
CN
2 3
and NH OSO H.
CN
As shown in eq. 4, our early investigation established the
feasibility of this approach. The oxime of picolinaldehyde was
converted to the corresponding nitrile in nearly quantitative yield
CN
CN
N
NO2
8
f, 85%
8h, 94%
8
g, 96%
8j, 99%
8
i, 87%
upon treatment with SO
2 2
F in the presence of triethylamine. The
Me
putative aminofluorosulfate intermediate was not observed.
CN
Br
CN
CN
S
MeO
MeO
CN
CN
OH
H
2
OSO F
NO2
k, 97%
Br
Me
N
N
SO
2
F
2, Et
3
N
8
8l, 92%
8m, 90%
8n, 90%
8o, 89%
N
N
N
CN
H
+
(4)
CH
2
Cl , rt
2
CN
CN
CN
H N
2
not observed
8
p, 84%
8q, 81%
O
8
r, 86%
Since aldoximes are readily formed from aldehydes in the
presence of hydroxylamine, we combined their synthesis and
subsequent conversion to nitriles in a one-pot reaction. We were
pleased to find that this transformation smoothly gave the
desired nitrile in high yield. As shown in Scheme 1, an aldehyde
Scheme 1. SO
aldehyde (0.5 mmol), NH
mL), rt. Vial II: MSDI (1 mmol), KHF
2
F
2
mediated synthesis of nitriles. Reaction conditions: Vial I:
OH•HCl (0.75 mmol), Et N (1.5 mmol), CH Cl (2
(2.5 mmol), H O (1 ml), rt, 3 hrs. 8d –
86%, 1.09 g, 8d – 93% in water/ethanol.
2
3
2
2
b
2
2
c
As shown in Scheme 2, from the total of 3 equivalents of
triethylamine (with respect to the starting aldehyde), 1.5
equivalents are used to free hydroxylamine from its
hydrochloride salt. The liberated hydroxylamine then reacts
with the aldehyde to produce the aldoxime. The reaction of
(
7) was simply dissolved in CH
hydrochloride (1.5 eq.) and triethylamine (3 eq.) to produce an
aldoxime, which was then treated with SO generated in a
separate reaction from methylsulfonyl diimidazolium salt (MSDI)
2 eq.) and KHF (5 eq.) in water (see Supporting Information for
details).
2 2
Cl , treated with hydroxylamine
2
F
2
(
2
2 2
aldoxime or its oximate anion with SO F results in a reactive
amino fluorosulfate intermediate which rapidly transforms to
nitrile and fluorosulfonic acid via a six-member transition state.
The pH of the reaction mixture after completion was ~3,
confirming the formation of an acidic by-product.
A variety of nitriles was generated in excellent yields using
this method. Electron-deficient and electron-rich aromatic
aldehydes
reacted
equally
well.
For
example,
4-
bromobenzonitrile (8d), 3-nitrobenzonitrile (8k) and 4-
methoxybenzonitrile (8e) were obtained in excellent yield. The
reaction is compatible with functional groups such as ketones,
amides and esters. Thus, 4-acetylbenzonitrile (8a), 4-
cyanophenylacetamide (8b), and methyl 4-cyanobenzoate (8c)
were obtained in high yields. Unsaturated cinnamaldehyde,
OH
H
O
R
N
O
O
NH2OH•HCl
N
SO2F
2
N
S
F
+
O
R
H
O O
S
Et
3
N
R
Et N
Et N
•
•
H2F2
HCl
3
R
H
3
+
HO
F
Et3N
via
2 2
Scheme 2. Plausible mechanism of the SO F -mediated nitrile synthesis.
heteroaromatic
picolinaldehyde,
and
thiophene-2-
To demonstrate versatility of the new method, we applied it
to both natural and synthetic molecules of biological
significance. Thus, vanillin 9 was readily converted to nitriles
carboxaldehyde reacted smoothly, producing the corresponding
nitriles (8f, 8g, and 8l). Olefins and alkynes remained intact
under these reaction conditions, as examples 8h and 8i
demonstrate.
1
1 and 13 (Scheme 3). Vanillin 9 was first converted to its 2-
[46]
hydroxyethyl derivative 10.
Treatment of aldehyde 10 with
produced nitrile 11.
Steric environment at the oxime’s carbon does not appear to
have an effect on the reaction. Thus, 2-nitrobenzonitrile (8j) 2,5-
dimethylbenzonitrile (8o) were obtained in high yield, as were
other polysubstituted aromatic nitriles. Aliphatic aldehydes, such
as 3-phenylpropanal and dodecanal readily engaged in the
reaction as well and produced nitriles 8p and 8q, respectively, in
good yield. The compatibility of this reaction with primary amides
was shown by synthesis of 4-cyanobenzamide (8r) in very good
yield. The reaction was scaled up to gram quantities as
exemplified by the synthesis of 4-bromobenzonitrile 8d, which
hydroxylamine, triethylamine and SO
2
F
2
The mesylated derivative 12 also gave the desired nitrile 13 in
high yield. The compatibility of the reaction with various
functional groups allows synthesis of azide functionalized
nitrile 14 starting from vanillin in excellent yield.
was obtained in 86% yield (1.09 g). This SO
2 2
F -mediated nitrile
synthesis can be also accomplished in an aqueous solution.
This article is protected by copyright. All rights reserved.

Chemistry - A European Journal
10.1002/chem.201805175
COMMUNICATION
CHO
(a)
OH
Br
CHO
NH2OH•HCl,
Et N, CH2Cl2
CN
CN
CN
CuSO
4
.5H
2
O
O
HO
HO
3
O
O
N
N
N
3
O
K
2
CO3, DMF
C, 4 hrs
O
HO
S
+
(10 mol%)
S
N
OMe
O
N
N
o
SO2F2, rt, 3 hrs
sodium ascorbate
(20 mol%)
F
O
6
5
OMe
F
O
9
, Vanillin
10
OMe
1, 78%
O
O
2
N
O
N
N
NO
2
1
Me
H O/ BuOH (1:1), rt
t
Me
o
2
MsCl, Et3N
CH2Cl2
0 C,
15 min
17
18
19, 95%
CN
(
1) NaN
0
3
C to rt
, DMF
CHO NH2OH.HCl,
Et N, CH2Cl2
CN
(b)
o
3
CN
H
N
N
3
OTBS
O
MsO
MsO
O
O
O
Me
CN
(2)
NH2OH•HCl,
Et N, CH2Cl2
SO2F2, rt, 3 hrs
O
O
+
DBU (20 mol%)
O
O
OMe
4, 94%
SO2F2, rt, 3 hrs
S
3
OMe
OMe
F
O
O
S
Me
N
H
DMF, rt
1
O
O
1
2
13, 87%
O
O
1
7
20
21, 91%
Scheme 3. Synthesis of nitrile derivatives of vanillin.
Scheme 5. Modification of polyfunctional nitrile 17 using (a) CuAAC and (b)
The mild reaction conditions allow facile synthesis of
densely functionalized polyfunctional probes which contain a
SuFEx reactions.
nitrile,
Scheme 4a) which allow downstream attachment of reporter
tags. Thus, 3,4-dihydroxy benzaldehyde was monoalkylated
a
fluorosulfate and alkyne or azide appendages
Selective introduction of some of the simplest functional
groups into complex organic molecules is not a trivial task.
The mild, red-ox neutral, water and oxygen compatible way to
selectively convert aldehydes to nitriles described here reliably
accomplishes this job. This practical one-pot synthesis should
prove useful whenever a direct, selective conversion of an
aldehyde to a nitrile is required. Inexpensive and readily
available reagents and mild reaction conditions make it
compatible with various functional groups, including amides,
ketones, esters, alcohols, alkynes, and alkenes. The reaction
performs well in aqueous solvents, providing a convenient
means of aldehyde and nitrile modification in biologically
important molecules, including peptides and imaging probes
containing chemically orthogonal handles that can be further
addressed using CuAAC and SuFEx chemistries.
(
[
47]
with propargyl bromide providing compound 16.
The
aldehyde group of this intermediate was converted to the
corresponding nitrile, and the remaining phenol was converted
to the fluorosulfate in one pot upon the treatment with
hydroxylamine and SO
2
F
2
.
The fluorosulfate can be
[
37,38]
addressed using sulfur(VI) fluoride exchange chemistry
to
form sulfate or sulfonamide derivatives, leaving the propargyl
handle for further functionalization using copper-catalyzed
[
48]
azide-alkyne cycloaddition (CuAAC, Scheme 4b).
To
illustrate this approach, we have modified the polyfunctional
probe 17 using CuAAC and SuFEx reactions.
(a)
CHO
CHO
NH OH•HCl,
Et3N, CH2Cl2
CN
Br
2
O
O
HO
S
HO
SO2F2, rt, 3 hrs
F
O
K2CO3, acetone,
rt, overnight
O
Acknowledgements
OH
O
1
5
16, 40%
17, 96%
This work was supported by the National Science Foundation
(
CHE-1660373).
O
S
CN
(b)
O
O
Keywords: Nitriles • sulfuryl fluoride • SuFEx • CuAAC • click
OSiR3
O
CN
reaction
SuFEx
F
S
Nitrile, sulfate cargo with
availabe CuAAC handle
O
N3
O
S
CN
F
CuAAC
N
N
O
N
Polyfunctional probes with orthogonally
functionalizable handles
Fluorosulfate: for SuFEx
Alkyne: for CuAAC
Nitrile, triazole cargo with
availabe SuFEx handle
[
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Scheme 4. Synthesis of nitriles with SuFEx and CuAAC handles.
[2]
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nitroimidazole was reacted with the alkyne handle of the
polyfunctional probe 17 using CuAAC click reaction to
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Chemistry - A European Journal
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J. Gurjar, J. Bater, V. V. Fokin*
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Sulfuryl Fluoride Mediated
Conversion of Aldehydes to Nitriles.
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