Controlled Access to C1-Symmetrical Cyclotriveratrylenes (CTVs) by Using a Sequential Barluenga Boronic Coupling (BBC) Approach

Article abstract of DOI:10.1002/adsc.202100547

We describe here a controlled approach to C₁-symmetrical cyclotriveratrylenes (CTVs). In this approach dimers are synthesized through Barluenga boronic coupling (BBC) and after borylation, the last aromatic ring is introduced by a second BBC. After functional transformations of the trimers, the CTVs are formed using intramolecular SEAr. (Figure presented.).

Full text of DOI:10.1002/adsc.202100547

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doi.org/10.1002/adsc.202100547
Controlled Access to C1-Symmetrical Cyclotriveratrylenes (CTVs)
by Using a Sequential Barluenga Boronic Coupling (BBC)
Approach
Clément Vigier,+a, b Pierre Fossé,+a, b Frédéric Fabis,a, b Thomas Cailly,a, b, c, d,* and
Emmanuelle Dubosta, b,*
a
Normandie Univ, UNICAEN, Centre d’Etudes et de Recherche sur le Médicament de Normandie (CERMN), 14000 Caen,
France
E-mail: emmanuelle.dubost@unicaen.fr; thomas.cailly@unicaen.fr
Institut Blood and Brain @Caen-Normandie (BB@C) Boulevard Henri Becquerel, 14074 Caen, France
CHU Côte de Nacre, Department of Nuclear Medicine, 14000 Caen, France
Normandie Univ, UNICAEN, IMOGERE, 14000 Caen, France
b
c
d
+
These authors contributed equally.
Manuscript received: May 7, 2021; Revised manuscript received: June 15, 2021;
Version of record online: July 9, 2021
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.202100547
cryptophanes[10–18] and hemicryptophanes.[19–26] To date,
most of these applications are based on the use of C3-
symmetrical CTVs and, for decades, C3-symmetrical
CTVs have been synthesized from the corresponding
Abstract: We describe here a controlled approach
to C1-symmetrical cyclotriveratrylenes (CTVs). In
this approach dimers are synthesized through
Barluenga boronic coupling (BBC) and after bor-
substituted benzylic alcohols through cyclotrimeriza-
ylation, the last aromatic ring is introduced by a
tion using acidic conditions such as perchloric acid in
second BBC. After functional transformations of the
methanol,[27] sulfuric acid in acetic acid,[10] formic
trimers, the CTVs are formed using intramolecular
acid[28] or scandium triflate.[29] This approach can be
SEAr.
applied only to specific substrates (e.g. arenes bearing
electron-donating groups in para position) and affords
products with poor to moderate yields. Whereas the
synthesis and the utility of C3-symmetrical CTVs are
well defined in the literature, the preparation and uses
of C1-symmetrical derivatives have been less studied.
Keywords: Crown compounds; Cyclotriveratrylene;
Supramolecular chemistry; Synthetic methods
To date, the most efficient approach to access C1-
Cyclotriveratrylene or CTV 1 (Figure 1) is a bowl- symmetrical CTVs is to desymmetrize C3-symmetrical
shaped achiral macrocyclic trimer of veratrole present- CTVs (Scheme 1, A) either by performing direct
ing a C3-symmetry. CTVs derivatives have found halogenation[18] or by modifying the nature of a
many applications as molecular platforms in the fields substituent on one of the aromatic rings.[30,31] Using the
of host-guest chemistry, supramolecular chemistry and same strategy, modification of the apical positions has
soft materials.[1] Indeed, when two different substitu- also been described through an oxidation to the
ents are introduced on the aromatic rings, the obtained corresponding ketone[32] followed by further trans-
derivatives 2 become chiral while still presenting a C3- formations such as Beckmann rearrangement.[33] Re-
symmetry. Modifications brought to one of the cently, another interesting approach has been reported
aromatic rings or one of the apical positions give rise in the literature by Martinez et al. (Scheme 1, B).[34] In
to C1-symmetrical CTVs (3, 4).
this paper, the authors propose the optimized prepara-
C3-Symmetrical CTVs have found a wide variety of tion of mixture of C1- and C3-symmetrical CTVs,
uses as ion or organic molecule sensors[2,3] building starting from a 1:1 ratio of benzylic alcohol position
blocks for liquid crystals[3] or purification devices.[4–6] isomers. The obtained stereoisomers were separated by
CTVs are also known to be precursors in chiral HPLC.
supramolecular assemblies such as capsules,[7–9]
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Scheme 2. Synthesis of boronic dimer 8.
uenesulfonyl hydrazide in 97% yield. The following
BBC allowed the formation of compound 6 in 97%
yield. In order to perform a second BBC, we tried to
synthesize boronic acid 8 through direct metal-halogen
exchange followed by electrophilic trapping with
trimethyl- or triisopropyl borate. Despite many at-
tempts, the preparation of 8 using this synthetic route
was not possible leading each time to complex
mixtures. However, when isopropoxypinacolborane
was used as the electrophile under the same metalation
conditions, we were pleased to isolate the correspond-
ing boronic ester 7 in 84% yield. As we found that
boronic ester 7 was nearly unreactive in BBC attempts,
Scheme 1. Structure of CTV 1, new and previously described
approaches toward C1-symmetrical CTVs.
In this work, we propose a new strategy to prepare the boronic acid 8 was synthesized after hydrolysis of
C1-symmetrical CTVs using the Barluenga boronic 7 with sodium periodate in 99% yield.
coupling (BBC) in an iterative and controlled approach
A second BBC between tosylhydrazone 5 and
(Scheme 1, C). This reaction, described in 2009, allows boronic acid dimer 8 was then performed to obtain
the formation of methylene bridges between two brominated trimer 9 in 74% yield (Scheme 3). In order
arenes in very mild conditions from widely available to reach the cyclization precursor 11, aldehyde 10 was
starting building blocks (hydrazones and boronic acids) prepared from metal-halogen exchange followed by
using a metal free reductive cross-coupling.[35] Since trapping of the lithiated species with DMF in 66%
then, many applications of this protocol have been yield. Reduction of 10 with NaBH4 afforded 11 in 99%
described in the literature, expanding the scope of CÀ C yield. Cyclization was then performed using perchloric
bond formation.[36–38] In order to obtain C1-symmetrical acid in excess for 18 h at room temperature and led to
CTVs using this reaction, we planned to synthesize an the expected CTV-3OMe 12 in 80% yield. Overall, the
open trimer bearing a benzylic alcohol which could be CTV-3OMe has been synthesized in 8 steps with 28%
obtained from two iterative BBCs. Once the trimer was overall yield and the efficiency of an iterative BBCs
obtained, a cyclization in acidic conditions will allow approach toward the synthesis of C3-symmetrical
access to C1-symmetrical CTVs while controlling the CTVs has been established. Even if this strategy
introduction and position of the new substituents
during the iterative BBCs process.
To set-up our synthetic strategy, we choose to
prepare a C3-symmetrical CTV, CTV-3OMe 12, known
in the literature as the key intermediate in the synthesis
of cryptophane-111 (Scheme 2).[12,39] As mentioned by
Miller et al.,[40] the steric hindrance of the boronic acid
coupling partner in BBC can be deleterious for the
reaction. A quick study of the substituents tolerated on
the coupling partners (see supporting information)
suggested that the coupling of hydrazone 5 and 3-
methoxyphenylboronic acid would give the best
results. Accordingly, tosylhydrazone 5 was prepared
from 2-bromo-4-methoxybenzaldehyde and para-tol-
Scheme 3. Synthesis of CTV-3OMe 12.
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requires more synthetic steps than the most efficient design of cryptophanes. Four substituted tosylhydra-
CTV-3OMe synthesis,[12] a similar overall yield was zones 13a–d were prepared from the corresponding
observed while avoiding lengthy purification proc- commercially available starting materials (see support-
esses.
ing information) and coupled with boronic acid dimer
In order to produce C1-symmetrical CTV using the 8 to afford brominated trimers 14a–d in 68–84%
same route, we investigated the preparation of C1- yields (Scheme 4). Metal-halogen exchanges were
symmetrical CTVs 18a–d bearing methoxy groups, performed, and trapping with DMF afforded the
because of their usefulness as key intermediates in the corresponding aldehydes 15a–d in 44–73% yields.
The reduction of 15a–d was performed using NaBH4
and afforded efficiently four cyclization precursors
16a–d substituted with allyl-, benzyl-, TBDMS- and
TIPS-protected phenol.
The cyclization step was then investigated (Ta-
ble 1). First, the cyclization was evaluated from the
allyl derivative 16a using an excess of perchloric acid
in methanol (entry 1). Under these conditions, the
cyclization didn’t occur and a complex mixture of
polymerized compounds was observed. The same
conditions were repeated with acetonitrile as the
solvent (entry 2) affording the deprotected C1-sym-
metrical CTV 17 within 20% yield along with
polymers. Performing the reaction in acetonitrile for
one hour at room temperature while reducing the
amount of perchloric acid to 1.2 equivalents allowed
us to isolate the O-allyl functionalized CTV 18a in
86% yield (entry 3). The same conditions were
Scheme 4. Synthesis of trimers 16a–d.
Table 1. Synthesis of C1-symmetrical CTVs 18a–d.
Entry
1
Starting material
Conditions
Results[a]
16a R=All
HClO4[b]/MeOH (1.6:3)
RT, 18 h
polymerisation
2
3
4
5
6
7
16a R=All
HClO4[a]/MeCN (1.6:3)
RT, 18 h
17 (20%)[c]
16a R=All
HClO4[b] (1.2 equiv.)
MeCN, RT, 1 h
HClO4[b] (1.2 equiv.)
MeCN, RT, 1 h
HClO4[b] (1.2 equiv.)
MeCN, RT, 1 h
P2O5 (1.3 equiv.)
MeCN, RT, 1 h
P2O5 (1.3 equiv.)
MeCN, RT, 1 h
18a (86%)
16b R=Bn
18b (91%)
16c R=TBDMS
16c R=TBDMS
16d R=TIPS
17 (98%)
17 (34%)/18c (58%)
18d (84%)
[a] Isolated yields;
[b] Aqueous HClO4 at 60% was used;
[c] Trace amount of 18a were also observed on the crude 1H NMR.
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repeated starting from the O-benzyl precursor 16b and prepare efficiently new C1-symmetrical CTVs 18a–d,
the corresponding CTV 18b was obtained in 91% inaccessible using existing procedures from the liter-
yield (entry 4). The use of these conditions onto the ature, while allowing the introduction of the asymme-
tert-butyldimethylsilyl protected intermediate 16c led try in the last stage of the synthesis from the common
quantitatively to the deprotected CTV 17 (entry 5). precursor 8. The flexibility of the sequence was further
Replacement of perchloric acid by phosphorus pent- illustrated in the production of the CTV 24 containing
oxide under the same conditions afforded the O- three different aromatic rings. Using this approach, the
TBDMS functionalized CTV 18c in 58% (entry 6) structural diversity of CTV could be considerably
along with 17 (34%). These latter conditions were widen by choosing the adequate synthetic partners.
repeated with the tri-isopropylsilyl protected intermedi- This strategy paves the way to the preparation of a
ate 16d affording the O-TIPS functionalized CTV 18c large amount of new CTVs with original structures
in 84% yield (entry 7).
thus enabling more applications with these macro-
To further demonstrate the ability of our strategy to cycles.
provide efficiently C1-symmetrical CTV, we chose to
illustrate its potency and flexibility through the syn-
Experimental Section
thesis of a CTV containing three different aromatic
rings (Scheme 5). First, compound 19 was synthesized Preparation of C1-CTV 24
in 82% yield starting from 2-bromo-meth-
1-Benzyl-2-bromo-4-methylbenzene 19
ylbenzaldehyde through a one-pot tosylhydrazone
formation followed by BBC. Metalation followed by
borylation afforded boronic ester 20 from 19 within
70% yield. Boronic ester 20 was then hydrolysed and a
BBC with tosylhydrazone 21 was directly initiated to
provide trimer 22 in 40% yield. Compared to our
previous attempts of BBC to obtain this kind of
trimers, the BBC temperature had to be reduced to
p-Toluenesulfonyl hydrazide (985 mg, 5.27 mmol) was added to
a solution of 2-bromo-4-methylbenzaldehyde (1 g, 5.02 mmol)
in dioxane (25 mL) and the mixture was stirred at 80 C for
°
1.5 h. Potassium carbonate (1.04 g, 7.53 mmol) and phenyl-
boronic acid (673 mg, 5.52 mmol) were added and the solution
was refluxed for 2.5 h. The resulting mixture was evaporated to
dryness, dissolved in ethyl acetate, washed with an aqueous
saturated solution of sodium bicarbonate and brine, dried over
MgSO4, filtrated and evaporated under vacuum. Purification
over silica gel (Cyclohexane/AcOEt 99/1) afforded the product
as a colorless oil (1.07 g, 82%).1H NMR (400 MHz, CDCl3):
δ=7.42 (s, 1H), 7.34–7.24 (m, 2H), 7.26–7.16 (m, 3H), 7.08–
6.99 (m, 2H), 4.09 (s, 2H), 2.31 (s, 3H).13C NMR (100 MHz,
°
60 C in order to allow isolation of 22. Performing the
reaction under reflux afforded 22 in a higher con-
version rate along with a side product co-eluting in all
our purification attempts. A metalation/formylation/
reduction sequence was then initiated from 22 to afford
benzylic alcohol 23 in 71% yield. This latter was CDCl3): δ=140.0, 138.0, 137.3, 133.4, 130.9, 129.1 (2C),
°
128.6 (2C), 128.4, 126.3, 124.7, 41.4, 20.7. HRMS-ASAP
cyclized with an excess of P2O5 at 60 C affording
calculated for C14H13Br [M+.] 260.0201, found 260.0203.
CTV 24 in 91% yield. Finally, compound 24 was
obtained with an overall yield of 15% with this 5-steps
sequence, thus demonstrating the ability of this
strategy to afford diversely functionalized C1-sym-
metrical CTV.
2-(2-Benzyl-5-methylphenyl)-4,4,5,5-tetramethyl-
1,3,2-dioxaborolane 20
n-BuLi 2.5 M in n-hexane (1.47 mL, 3.65 mmol) was added to
a solution of 19 (530 mg, 2.03 mmol) in 8 mL of dry THF at
In conclusion, we have demonstrated an iterative
BBC approach toward CTVs allowing their controlled
preparation. This strategy has been validated in the
preparation of a known C3-symmetrical CTV, CTV-
3OMe, and presents an alternative route to this
compound. Moreover, our methodology can be used to
°
À 78 C. The solution was stirred for 1 hour and iPrOBPin
(0.54 mL, 2.64 mmol) was added. The mixture was stirred at
°
À 78 C for 2 h and subsequently warm to room temperature
over 1 hour. The reaction was quenched with water and
extracted with EtOAc. The combined organic phases were dried
over MgSO4, filtered and concentrated under vacuum. Purifica-
tion over silica gel (Cyclohexane/AcOEt 98/2) afforded the
1
product as a yellow oil (436 mg, 70%). H NMR (400 MHz,
CDCl3): δ=7.63 (d, J=2.1 Hz, 1H), 7.25–7.20 (m, 2H), 7.18–
7.11 (m, 4H), 7.06 (d, J=7.8 Hz, 1H), 4.29 (s, 2H), 2.32 (s,
3H), 1.27 (s, 12H). 13C NMR (100 MHz, CDCl3): δ=144.5,
142.9, 136.7 (2C), 134.8, 131.9, 130.2, 129.1 (2C), 128.2 (2C),
125.6, 83.6 (2C), 40.6, 24.9 (4C), 21.0. HRMS-ESI calculated
for C20H25BO2 [M+H+] 309.2026, found 309.2039.
Scheme 5. Synthesis of CTV 24.
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(m, 3H), 7.05–7.02 (m, 1H), 6.86 (d, J=8.2 Hz, 1H), 6.67 (s,
1H), 4.41 (d, J=5.7 Hz, 2H), 3.93 (s, 2H), 3.85 (s, 2H), 2.25 (s,
3H), 1.41 (t, J=5.8 Hz, 1H).13C NMR (100 MHz, CDCl3): δ=
140.69, 140.59, 137.87, 136.61, 136.32, 135.89, 132.44, 131.38,
130.88, 130.35, 128.75, 128.59, 127.77, 127.77, 127.56, 126.22,
77.16, 62.55, 39.10, 34.88, 21.21. HRMS-ASAP calculated for
C22H19Cl [M-H2O] 318.1175, found 318.1169.
N’-[(Z)-(2-Bromo-4-chlorophenyl)methylidene]-
4-methylbenzene-1-sulfonohydrazide 21
In a round bottom flask, p-toluenesulfonyl hydrazide (892 mg,
4.79 mmol) was solubilized in methanol (4 mL/g). 2-bromo-4-
chlorobenzaldehyde (1 g, 4.56 mmol) was added to the solution,
the resulting mixture was stirred for 2.5 h. The resulting mixture
was evaporated to dryness, dissolved in a small portion of
diethyl ether. The solid was filtered, and the expected product
was obtained as a white powder (1.72 g, 98%). 1H NMR
(400 MHz, CDCl3): δ=8.05 (s, 1H), 7.90 (s, 1H), 7.88–7.85
(m, 2H), 7.83 (d, J=8.5 Hz, 1H), 7.54 (d, J=2.0 Hz, 1H), 7.33
(d, J=8.0 Hz, 2H), 7.29 (dd, J=8.6, 2.0 Hz, 1H), 2.42 (s,
3H).13C NMR (100 MHz, CDCl3): δ=144.7, 136.9, 135.2,
132.8 (2C), 130.8, 130.0 (2C), 128.6, 128.3, 128.1 (2C), 124.2,
C1-CTV 24
Phosphorus pentoxide (697 mg, 2.4 mmol) was added to a
solution of 23 (80 mg, 0.24 mmol) in acetonitrile (48 mL) and
°
the mixture was stirred at 60 C for 1 h. The reaction was
quenched with an aqueous solution of saturated NaHCO3,
extracted with AcOEt, washed with brine, dried over MgSO4
and concentrated under vacuum. Purification over silica gel
(cyclohexane/AcOEt 95/5) afforded the product as a white
°
21.8. Melting Point: 185–187 C. HRMS-ESI calculated for
C14H13BrClN2O2S [M+H+] 386.9570, found 386.9753.
1
powder (62 mg, 91%). H NMR (400 MHz, CDCl3): δ=7.31–
7.26 (m, 2H), 7.25–7.15 (m, 3H), 7.06–7.01 (m, 3H), 6.98 (dd,
J=8.3, 2.2 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 4.74 (dd, J=
15.7, 13.7 Hz, 3H), 3.68–3.55 (m, 3H), 2.16 (s, 3H).13C NMR
(100 MHz, CDCl3): δ=141.4, 139.9, 138.8, 138.7, 138.2,
136.7, 136.5, 132.3, 131.5, 130.6, 130.2, 130.19, 130.15, 129.9,
128.1, 127.4, 127.2, 127.1, 37.1, 36.9, 36.6, 21.1. Melting
°
1-[(2-Benzyl-4-methylphenyl)methyl]-2-bromo-
4-chlorobenzene 22
To a solution of 20 (314 mg, 1.4 mmol) in a mixture of THF
(12 mL) and H2O (5 mL) at room temperature, NaIO4 (895 mg,
4.2 mmol) was added. The solution was stirred at room
temperature, under air for 30 minutes. Aqueous 1 M HCl
(2.1 mL, 2.1 mmol) was then added to the reaction mixture and
the solution was stirred at room temperature for 18 h, over
which time a white solid precipitated. The reaction mixture was
quenched with H2O and extracted with EtOAc. The combined
organic phases were dried over MgSO4, filtered and concen-
trated under vacuum to afford the product as an oil.
Point:
206–208 C.
HRMS-ASAP
calculated
for
*
C22H19Cl [M+ ] 318.1175, found 318.1171.
Acknowledgements
The authors are grateful for financial support provided by the
Regional Council of Normandy, FEDER, the University of Caen
and Tremplin Carnot I2C. We thank Dr. V. Babin for fruitful
discussions about chemistry.
In a round bottom flask, 21 (451 mg, 1.17 mmol) was
solubilized in dioxane (15 mL/mmol). Potassium carbonate
(4 equiv.) and crude boronic acid (1.5 equiv.) were added, and
the solution was heated at reflux for 2.5 h. The resulting mixture
was allowed to reach room temperature and an aqueous
saturated solution of sodium bicarbonate was added (15 mL/
mmol). The mixture was extracted three times with ethyl
acetate. The organic layers were combined, dried over MgSO4,
filtered and evaporated under vacuum. The crude mixture was
purified using silica chromatography using cyclohexane/ethyl
acetate (95/5) as the eluent, affording the expected product as a
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