Facile Access to AgOCF3 and Its New Applications as a Reservoir for OCF2 for the Direct Synthesis of N?CF3, Aryl or Alkyl Carbamoyl Fluorides

Article abstract of DOI:10.1002/chem.202000116

The development of innovative fluorination strategies is greatly dependent also on the availability, safety and practicability of available fluorinating reagents. We herein show a straightforward and quantitative strategy for the preparation of valuable AgOCF₃ at room temperature and showcase its performance in trifluoromethoxylations or as reservoir for O=CF₂. This enabled the direct, practical and safe synthesis of valuable N-alkyl/aryl and N?CF₃ carbamoyl fluorides from secondary amines and isothiocyanides, respectively. Our mechanistic data indicate that AgOCF₃ does not liberate O=CF₂ until it is activated by a nucleophilic co-reagent, reinforcing the stability of the salt under our new preparation strategy.

Full text of DOI:10.1002/chem.202000116

A Journal of
Accepted Article
Title: Facile Access to AgOCF3 and Novel Applications as Reservoir
for OCF2 for the direct Synthesis of N-CF3, Aryl or Alkyl
Carbamoyl Fluorides
Authors: Abdur Turksoy, Thomas Scattolin, Sam Bouayad-Gervais,
and Franziska Schoenebeck
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
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the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Chem. Eur. J. 10.1002/chem.202000116
Link to VoR: http://dx.doi.org/10.1002/chem.202000116
Supported by

Chemistry - A European Journal
10.1002/chem.202000116
DOI: 10.1002/anie.201((will be filled in by the editorial staff))
Fluorine Chemistry
Facile Access to AgOCF
3
and Novel Applications as Reservoir for OCF
2
for the direct Synthesis of N-CF
3
, Aryl or Alkyl Carbamoyl Fluorides
Abdur Turksoy, Thomas Scattolin, Sam Bouayad-Gervais and Franziska Schoenebeck*
Abstract: The development of innovative fluorination strategies is
greatly dependent also on the availability, safety and
practicability of available fluorinating reagents. We herein
present a straightforward and quantitative strategy for the
Triflumuron
Riluzole
Thifluzamide
preparation of valuable AgOCF
showcase its performance in trifluoromethoxylations or as
reservoir for O=CF . This enabled the direct, practical and safe
synthesis of valuable N-alkyl/aryl and N-CF carbamoyl fluorides
from secondary amines and isothiocyanides respectively. Our
mechanistic data indicate that AgOCF does not liberate O=CF
3
at room temperature and
Insect Growth Regulant
Medication for ALS Patients
Fungicide
2
3
3
2
Penicillin Core
Mexiletine Derivative Nortriptyline Derivative
until it is activated by a nucleophilic nitrogen, reinforcing the
stability of the salt under our new preparation strategy.
Current methods to access AgOCF3
AgF, MeCN
AgF or
O
wing to the beneficial effects of fluorination on the physical
AgOCF3
-
40 °C
AgF, CsF
-ArSO2F
properties of organic molecules, such as increasing their lipophilicity
or metabolic stability features paired with inverted charge or
-
CF SO F
3
2
TFMT
TFMS
[
1]
conformational distributions, there is a significant demand for the
development of novel fluorination strategies.[1e, 1f, 2] In this context,
the wider applicability of any developed methodology will ultimately
also depend on the accessibility of the fluorination agents as well as
their overall sustainability. For example, the installation of the
trifluoromethoxy group (“OCF
halogen”
molecules (high lipophilicity, biostability) and materials (lowering
Volatile & expensive reagent (BP: 19 °C)
Degassing with Ar to remove CF SO F
Stoichiometric organic by-products
Purification to remove ArSO2F
3
2
R: CF , alkyl, aryl
This work:
3
MeCN, r.t.
AgF
+
CO(OCCl
3
)
2
AgOCF3
stable
3
”) – also known as a “super-
AgCl
solid
solid
[
3]
that induces advantageous properties in bioactive
[
4]
Quantitative
Purified by simple filtration
Reactivity & Mechanism
[
3, 5]
surface tension or dielectric constants),
AgOCF as trifluoromethoxylation reagent. AgOCF
generally prepared as a stock solution from reaction of AgF with the
frequently relies on
Figure 1. A) Biologically active and relevant fluorinated compounds; B) Current
approaches to access AgOCF ; the stock solution reparation on the left, in-situ
[
6]
3
3
in turn is
3
preparation on the right, and this work.
[
6c, 7]
highly volatile liquid CF
3
SO
2
OCF
3
(TFMT; BP: 19 °C).
As such,
rather low temperature (i.e. -40°C) needs to be maintained throughout
We envisioned that the minimalistic approach to AgOCF would
3
the reaction to avoid the loss of the reagent. Moreover, the by-product
essentially be the direct addition of AgF to fluorophosgene (F C=O).
2
(
CF
solution with argon (Figure 1, B). Recently, researchers attempted
to devise less tedious strategies to generate the required AgOCF in
3
SO
2
F) subsequently needs to be removed by purging of the stock
While this transformation would formally be waste-free, the fact that
fluorophosgene is a toxic and corrosive gas, would make the overall
process less practical. However, we recently showed that the
subjection of AgF to the solid reagent bis(trichloromethyl) carbonate
[
6c]
3
situ from suitable organic precursors. In this context, trifluoromethyl
aryl sulfonates (TFMSs) have been widely utilized, which in
(BTC) leads to in-situ liberation of O=CF along with AgCl
2
combination with AgF release AgOCF3.[
6g, 6h, 6j]
However, this
[9a]
formation.
As such, and in view of practicability, safety and
approach leads to the generation of stoichiometric organic by-
products, which eventually either need to be removed or if remaining
in situ, these side-species could potentially perturb the transformation
of interest, especially more sensitive metal-catalysed approaches .
As part of our ongoing program in developing efficient methods
for the installation of (heteroatom-containing) fluorinated motifs,[9]
we set out to develop a practical and quantitative approach to access
minimal production of waste, we chose to study the reaction between
the solid reagent BTC (0.33 equiv.) with AgF (3 equiv.) in MeCN. To
this end, we added MeCN in single portion to a vial containing both
solids at room temperature and stirred the mixture overnight (18 h) at
room temperature. We subsequently filtered the insoluble material,
(i.e. AgCl) under an inert atmosphere (Figure 2), and its facile
[
8]
[
10]
recovery offers the opportunity for recycling. To our delight, the
AgOCF
3
and used the reagent in novel applications to access highly
remainder in solution proved to be AgOCF , which formed
quantitatively and exclusively as judged by F-NMR spectroscopic
analysis. Importantly, we repeated the experiment also at larger scale
3
1
9
valuable fluorinated amine motifs.
(up to 1.5 g scale) and the reaction proceeded equally efficiently.
There was also no need for cooling or careful reaction control.
1
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Chemistry - A European Journal
10.1002/chem.202000116
Moreover, the AgOCF
times. In our tests, we found it to be unchanged and equally reactive
after storage for three months (at -30°C under inert conditions).
3
solution appears to be storable for extended
diazo-2-phenylacetate at room temperature yielded the corresponding
1
9
OCF
reports.
Having established that our newly developed approach to
AgOCF can readily be applied in a variety of known AgOCF
reactions, without any compromise on yield or efficiency, we
subsequently set out to investigate novel applications of the AgOCF
reagent in synthesis. We recently reported the first straightforward
and general access to N-CF carbonyl containing molecules, (i.e. N-
CF
amides, ureas, carbamates and thiocarbamates).[9a] The
3
ester (42% based on F-NMR) in comparable yield as previous
[
6f]
3
3
MeCN
RT, Overnight
AgF
+
CO(OCCl3)2
(0.33 equiv.)
OCF2
AgOCF3
+
AgCl(s)
. Scalable
. Quantitative
. Practical
(
3 equiv.)
-
27.1 ppm in
Stable Silver
Source
3
19
F-NMR
Substitute
3
3
transformation relied on the initial conversion of isothiocyanates to
N-trifluoromethylcarbamoyl fluorides, which in turn were readily
diversified. The latter forms through initial desulfurization of the
Before the reaction
Completed reaction
(solid by-product)
Filtration step to
isolate AgOCF stock solution
(solid reagents)
isothiocyanate with AgF, resulting in RN=CF
with AgF and is trapped with O=CF . Given that AgOCF
principle reversibly release O=CF and AgF, we were intrigued to
examine whether subjection of our prepared AgOCF to a number of
isothiocyanates (R-N=C=S) results in direct formation of the vital N-
CF carbamoyl motif. To our delight, we observed efficient
transformation of isothiocyanate 5a with the AgOCF stock solution
2
, which reacts further
3
2
3
could in
1
)
PPh , ICH CH I
DMF
3
2
2
2
AgOCF3
MeCN, 12h
30 °C to RT
R-X
R-OCF
3
R-OH
R-OCF
3
2) AgOCF , 80 °C
3
3
1
2
3
4
-
15 min
X=Br
3
3
under air at 50 ºC within 18 hours. We successfully prepared a
number of N-trifluoromethylcarbamoyl fluorides in good to excellent
yields (Figure 3A). Importantly, the only by-product in this
2
a. 82%
2b. 94%
2d. 95%
4a. 73%
4b. 32%
2
transformation is Ag S, which we collected through filtration of the
reaction mixture (see Figure 3B (top part)), leaving the carbamoyl
fluoride essentially pure after solvent removal. Our previous
2c. 96%
4c. 85%
4d. 61%
[
9a]
method used 5 equiv. of silver salt, while the current only formally
needs two equivalents (excluding those used to make AgOCF ). As
such, we also set out to test the reactivity of in situ generated AgOCF
from trifluoromethyl benzene sulfonate with AgF. This also gave the
efficient formation of the N-CF carbamoyl motif of 5c with 65%
X=I
3
2
e. 98%
4e. 68%*
3
Figure 2. The synthesis of AgOCF
after (middle) the reaction and filtration over a syringe filter to isolate the stock
solution of AgOCF (right). A) Substitution scope with benzyl bromides and alkyl
3
stock solution (top). Reactants before (left),
3
yield based on 19F-NMR, and therefore allows to apply this
methodology readily to applications where the use of silver is desired
to be minimized. Electron-rich and deficient aromatic, heterocyclic as
well as alkyl isothiocyanates underwent smooth transformation, see
Figure 3A.
3
iodide; B) the dehydrotrifluoromethoxylation of alcohols. *Alkyl alcohols require
allyl diphenyl phosphine & 100 °C.
We subsequently set out to test whether the AgOCF
our new approach would give similar reactivity to differently
synthesized AgOCF reagents. To this end, we subjected our AgOCF
stock solution to benzyl bromides and an alkyl iodide at room
temperature for 12 h. The corresponding substitution reactions proved
to be highly efficient independently of the substitution pattern of the
reactant (ortho, meta or para), see Figure 2A (2a-2e). Unlike to
previously reported by-products in substitution reactions with
trifluoromethoxy anions,
amount of fluorinated by-products. This suggests that our practical
preparation of AgOCF at room temperature has no adverse impact
on reactivity or stability; in fact, the AgOCF appears to be stable in
the reaction medium even for extended periods of time. Similarly, our
AgOCF stock solution also performed well in reactions with alcohols
to produce R-OCF at up to 100°C reaction temperature (see Figure
B); this otherwise known[6e] transformation relies on the generation
3
prepared via
To unambiguously confirm our hypothesis that AgOCF
release O=CF and AgF in situ, we undertook a series of ReactIR
investigations. We initially monitored whether AgOCF
spontaneously releases O=CF upon heating; however, there was no
sign of any change and AgOCF appears to be stable for several hours
3
would
2
3
3
3
2
3
at 50 ºC in solution by itself (see SI for React IR profile). We
subsequently conducted the analogous monitoring for the actual
transformation, i.e. in the presence of isothiocyanate 6c at 50°C. The
resulting profile is shown in Figure 3B (bottom part). There is an
[
6d, 7]
we did not observe any considerable
-1
initial consumption of AgOCF
proportional formation of O=CF
This is likely the result of destabilization of the AgOCF
3
(974 cm ) as well as an instantly
3
-1
2
(characteristic signal at 1245 cm ).
salt by
3
3
isothiocyanate coordination, which appears to trigger the
fluorophosgene liberation. The reaction profiles monitored at both,
25ºC and 50ºC, showed clear formation of a compound with a
3
3
2
-1
+
-
characteristic signal at 1641 cm , which we previously assigned to be
3
of an iodophosphonium salt (R IP I ) and Vilsmeier-Haack-type
[
9a]
the desulfurization product, i.e. R-N-C=F
AgOCF the N-CF carbamoyl fluoride 6c (characteristic band at
848 cm ) appeared. As such, AgOCF displays rather high thermal
stability and only liberates O=CF through coordination with the
isothiocyanate, which subsequently desulfurizes upon reaction with
2
.
Upon addition of
intermediate which can activate alcohols to form the
trifluoromethoxylated product through dehydration. Another popular
reaction is the silver mediated transformation of α-diazo esters into α-
3
3
-1
1
3
[
6f]
2
OCF
esters utilized both AgOCF
trifluoromethoxide anion from trifluoromethyl triflate (TFMT) with
AgF. Subjection of our stable stock solution of AgOCF to ethyl 2-
3
esters. The reported precedence for the synthesis of α-OCF
3
W
3
stock solution and in situ release of the
the silver in solution and ultimately generates the R-NCF
3
COF upon
trapping with O=CF (see Figure 3B, bottom).
2
3
2
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Chemistry - A European Journal
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Suggested Mechanism
Complexation &
Destabilization
5
6
7
8
Desulfurization
6a. 99%
6b. 99%
6c. 95%
Intermediate at 1641 cm-1
8a. 96%
8b. 80%
8c. 99%
ReactIR Profile
AgOCF3
0
0
0
.3
.2
.1
0
6d. 95%
6e. 99%
6f. 99%
8d. 91%
8e. 93%
8f. 99%
15
20
Time (min) 25
30
strategic alternative to minimize silver
6g. 95%
6h. 91%
6i. 95%
8g. 93%
8h. 99%
Figure 3. A) Scope of formation of N-trifluoromethylcarbamoyl fluoride derivatives from isothiocyanates under air at 50 oC for 18 hours; B) suggested mechanism for
the formation of N-trifluoromethylcarbamoyl fluorides from isothiocyanates (top part), the graphical representation of ReactIR profile of the reaction at 50 ºC (middle
3
part), the synthesis of 6c via in situ generation of AgOCF (bottom part); C) scope of formation of carbamoyl fluorides from secondary amines at room temperature.
These data indicate that AgOCF
3
is a rather stable reservoir of
themselves or powerful intermediates to N-alkyl/aryl or N-CF
3
O=CF which only gets “activated” upon coordination of a
2
amides, ureas or (thio)carbamates.
nucleophilic reaction partner. To this end, we envisioned that
subjection of secondary amines might allow the direct generation of
N-disubstituted carbamoyl fluorides. Such compounds in turn have
shown activities and applications as insecticides or esterase
inhibitors, and serve as valuable intermediates in the synthesis of
unsymmetrical, disubstituted carbonyl compounds. While traditional
synthetic approaches involve highly toxic and gaseous reagents,[12]
there have recently been elegant advances involving the direct
Acknowledgements
We gratefully acknowledge RWTH Aachen University for financial
support.
[
11]
Conflict of interest
[
13]
conversion of amines with CO
2
and a deoxyfluorination reagent,
or using difluorocarbenes. Pleasingly, the subjection of secondary
amine 8a to AgOCF along with the base (DIPEA) at room
The authors declare no conflict of interests.
[
14]
Received: ((will be filled in by the editorial staff))
Published online on ((will be filled in by the editorial staff))
3
temperature gave the corresponding carbamoyl fluorides within 2h
reaction time. We explored a number of examples; electron-rich,
deficient and heterocyclic (8c) amines as well as drug derivative 8g
and the Boc-protected amine (8f) all generated the corresponding
carbamoyl fluorides in high yields (see Figure 3C) without any
Keywords: fluorination • OCF
mechanism • carbamoyl fluoride
3
• N-trifluoromethyl • synthesis •
[
15]
formation of double addition products.
As such, this method
presents a convenient, safe and highly practical route into carbamoyl
fluorides.
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10.1002/chem.202000116
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4
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Chemistry - A European Journal
10.1002/chem.202000116
Fluorine Chemistry
R: CF3,
MeCN, r.t.
A. Turksoy, T. Scattolin, S. Bouayad-
Gervais, F. Schoenebeck*
alkyl, aryl
AgF
solid
+
CO(OCCl3)2
AgOCF3
stable
AgCl
solid
Page – Page
Quantitative
Purified by simple filtration
Reactivity & Mechanism
Facile Access to AgOCF
3
and Novel
Applications as Reservoir for OCF
2
for
the Direct Synthesis of N-CF
3
, Aryl- or
Alkyl Carbamoyl Fluorides
5
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