Synthesis of tetronic acids from propargylic alcohols and CO2

Article abstract of DOI:10.1039/c8cc03039a

A direct and practical synthesis of important tetronic acids from easily available propargylic alcohols and carbon dioxide is reported for the first time. This transition-metal-free transformation features high atom- and step-economy, mild reaction conditions, good functional group tolerance and high yield. Preliminary mechanistic studies suggest that the reaction proceeds via cyclization to give alkylidene cyclic carbonate, ring-opening and re-cyclization processes.

Full text of DOI:10.1039/c8cc03039a

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DOI: 10.1039/C8CC03039A
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Synthesis of tetronic acids from propargylic alcohols and CO2
Guo Shen,a Wen-Jun Zhou,a,b,* Xiao-Bo Zhang,a Guang-Mei Cao,a Zhen Zhang,a,c Jian-Heng Ye,a Li-Li
Liao,a Jing Li,a and Da-Gang Yua,*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A direct and practical synthesis of important tetronic acids from
easily-available propargylic alcohols and carbon dioxide is
reported for the first time. This transition-metal-free
transformation features high atom- and step-economy, mild
reaction conditions, good functional group tolerance and high
yield. Preliminary mechanistic studies suggest that the reaction
proceeds via cyclization to give alkylidene cyclic carbonate, ring-
opening and re-cyclization processes.
appealing but challenging.
Carbon dioxide (CO2), well-known as the greenhouse gas, is
also an important C1 synthon in organic synthesis owing to its
abundance, easy availability, and low toxicity. Although the
thermodynamic stability and kinetic inertness make it difficult
to be utilized efficiently, various kinds of selective organic
transformations of CO2 have been achieved in recent years.1
Among them, numerous effort has been devoted to the
synthesis of alkylidene cyclic carbonates from propargylic
alcohols with CO2 (Scheme 1).1i,1l,2 Diverse catalysts, such as
silver,3 zinc,4 copper,5 palladium,6 cobalt,7 ruthenium,8
phosphine,9 N-heterocyclic carbene (NHC),10 N-heterocyclic
olefin (NHO),11 ionic liquids (ILs),12 and base,13 have been
proven to significantly promote this transformation. In
contrast, the straightforward transformations to other high-
value-added chemicals from propargylic alcohols with CO2 are
less developed. For example, Yamada and co-workers reported
the elegant Ag-catalyzed rearrangement of propargylic
alcohols to form α,β-unsaturated ketones containing the
oxygen from CO2.14 Jiang, Qi, Yuan, Liu and Wang reported the
novel CO2-mediated hydration of propargylic alcohols to give
α-hydroxyl ketones15 or 3(2H)-furanones.16 Although CO2 is
vital to these transformations,15-16 it is not incorporated into
these products. The generation of other important chemicals
from propargylic alcohols with incorporation of CO2 is highly
Scheme 1 Incorporation of CO2 into aryl propargylic alcohols
Tetronic acids are valuable intermediates and important
motifs in agricultural, pharmaceutical, and biological
chemistry.17 Plenty of routes have been developed to prepare
them.18 However, many of them suffer from long synthetic
routes, harsh reaction conditions or unstable starting materials.
Thus, an alternative strategy to synthesize tetronic acids from
simple and readily-available substrates in a sustainable process
is highly desirable. As an ongoing endeavour to demonstrate
the wide applications of CO2 in organic synthesis,19 we report a
novel and practical method for the synthesis of tetronic acid
derivatives from propargylic alcohols and CO2 for the first time.
This transition-metal-free process features mild reaction
conditions, high atom- and step-economy, good functional
group tolerance and high yield (Scheme 1).
When we tested the reaction of 4-(3-hydroxy-3-methylbut-
1-yn-1-yl)benzonitrile 1a with CO2 in 1,3-dimethyl-2-
imidazolidinone (DMI), we were unexpected to obtained the
tetronic acid 2a in 19% yield (Table 1, entry 1). The interest in
this important tetronic acid drove us to further investigate the
reaction conditions. Next, various kinds of bases (Table 1,
entries 2-10) were screened. To our delight, the reaction
proceeded smoothly in the presence of Cs2CO3 to give the
desired product 2a in 90% isolated yield (Table 1, entry 8).
Subsequently, we also tested different solvents and found that
DMI behaved better than other solvents (Table 1, entries 11-
16). It is worth noting that shorter reaction time also led to
high yield in this case, as the reaction also afforded 2a in 86%
yield in 2 hours (Table 1, entry 17). Although higher efficiency
of this transformation with more equivalents of base was
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View Article O2nlsin)e,
observed, the reaction with less amount of Cs2CO3 also groups, including fluoro (2i), chloro (2j), bromo (2k and
provided 2a in moderate to excellent yield (Table 1, entries 18 ester (2n), nitro (2o), trifluoromethyl (D2OpI):,10k.e10to39n/eC8(C2Cq0),30a3n9dA
and 19). Notably, the inductively coupled plasma mass methoxyl (2u), were well tolerated in this reaction, which
spectrometry (ICP-MS) test indicated that this reaction was a provided huge opportunities for subsequent transformations.
transition-metal-free process (please see ESI for more details).
Besides para-substituents (2i
-2r), the substrates with ortho-
(
2s and 2t) or meta- (2u and 2v) substitutions on the arenes
Table 1 Reaction conditions optimizationa
were suitable to the reaction, providing desired products in
moderate to good yields. To our delight, propargylic alcohols
bearing pyridine (2w) or naphthalene (2x) could also react
smoothly. Notably, a gram-scale synthesis of 2s was carried
out with the yield of 79% under the standard conditions,
demonstrating the applicability of this method. Unfortunately,
those substrates bearing alkyl or just hydrogen at 3-position of
propargylic alcohols are not suitable for this reaction.
Entry
Base
Solvent
Yield (%)
1
2
3
DBU
MTBD
DABCO
TBD
DMI
DMI
DMI
DMI
DMI
DMI
DMI
DMI
DMI
DMI
DMF
DMA
NMP
DMSO
MeCN
THF
19
31
0
68
N.D.
4
52
90 (90)
8
Table 2 Substrate scope a
4
5
6
7
8
Li2CO3
Na2CO3
K2CO3
Cs2CO3
CsF
9
10
11
12
13
14
15
16
17b
18c
19d
CsOAc
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
7
38
63
71
51
38
9
86
55
82
DMI
DMI
DMI
a
Reaction conditions: 1a (0.4 mmol), 1 atm of CO2, base (4 equiv.), solvent (3 mL),
65 °C, 48 h. Determined by UPLC using benzophenone as internal standard. The yield in
b
parentheses is isolated yield. 2 h. c 1 equivalent of Cs2CO3 was used. d 2 equivalents of
Cs2CO3 was used. N.D. = Not Detected. DMF = N,N-dimethylformamide. DMA = N,N-
dimethylacetamide. NMP = N-methyl-2-pyrrolidone. DMSO = dimethyl sulfoxide. THF =
tetrahydrofuran. DBU
hexahydro-1-methyl-2H-pyrimido[1,2-α]pyrimidine.
diazabicyclo[2.2.2]octane. TBD = 1,5,7-triazabicyclo[4.4.0]dec-5-ene.
=
1,8-Diazabicyclo[5.4.0]undec-7-ene. MTBD
=
1,3,4,6,7,8-
1,4-
DABCO
=
With the optimized reaction conditions in hand (Table 1,
entry 8), we first investigated the substrates with different
substituents at the α-position of hydroxyl group (Table 2). The
substrates with both symmetric (1a and 1c) and unsymmetric
dialkyl groups (1b) could provide the desired products in good
yields. The substrate 1d with methyl and phenyl substitution
also worked well to deliver the corresponding product 2d in 87%
yield. Moreover, the cyclic tertiary alcohols, including five- (1e),
six- (1f), and seven-membered rings (1g), also afforded the
tetronic acids 2e-g with excellent yields.
a
Reaction conditions: propargylic alcohol 1 (0.4 mmol), Cs2CO3 (4 equiv.), 1
b
atm of CO2, 3 mL of DMI, 48 h, 65 °C. Yield of isolated products. Cs2CO3 (2
equiv.). c 2 h.d The yield of gram-scale reaction.
Next, we tested the substrates with different substitutions
on the arenes. We found that diverse aryl propargylic alcohols
bearing electron-withdrawing groups (EWGs) or electron-
donating groups (EDGs) could afford the desired products 2h-
2x in 56%-86% yields. It was obvious that substrates bearing
EWGs showed higher reactivity than those with EDGs at the
para position, which might benefit from the higher
electrophilicity of the C─C triple bond toward in-situ generated
carbonate anion. The structure of 2h was confirmed by the X-
ray crystal structure analysis.20 Various kinds of functional
To gain more insight into the reaction mechanism, a series
of control experiments were conducted (Scheme 2). Firstly, 2h
could not be formed either under N2 atmosphere or in the
absence of base, highlighting the crucial role of CO2 and base
in this transformation (eq. 1). Moreover, 2h’ was obtained
with 92% 13C label in 72% yield when 13CO2 was used (please
see ESI for more details), which clearly indicated that the
carbonyl group came from CO2 (eq. 2). Since we detected 5-
benzylidene-4,4-dimethyl-1,3-dioxolan-2-one 3h, which was
2 | J. Name., 2012, 00, 1-3
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reported as the desired product in previous works,3-13 in some
cases with different reaction conditions, we further
investigated the role of this species. We found that the
tetronic acid product 2h could be obtained in moderate to
good yield in the reaction of 3h under either standard
conditions or N2 atmosphere (eq. 3). These results indicated
that cyclic carbonate 3h might be a competent intermediate.
Notably, 2h was not detected without Cs2CO3, indicating that
the base is vital for the generation of tetronic acid from
alkylidene cyclic carbonate (eq. 3). Moreover, 3-hydroxy-3-
methyl-1-phenylbutan-2-one 4h, another product in previous
work,15 afforded no desired product 2h under standard
reaction conditions, excluding the possibility of 4h as the
intermediate (eq. 4).
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DOI: 10.1039/C8CC03039A
Scheme 3 Proposed mechanism
In conclusion, we have reported the first method for the
synthesis of important tetronic acids from aryl propargylic
alcohols with CO2. This transition-metal-free and practical
process takes place with easily-available and nontoxic starting
materials, high atom-economy and step-economy under mild
reaction conditions. Besides, this novel method generates the
important products with good functional group tolerance and high
yields. Preliminary mechanistic studies suggest that the reaction
proceeds via cyclization, ring-opening and re-cyclization processes.
Further mechanistic studies are underway in our laboratory.
Conflicts of interest
There are no conflicts to declare.
Scheme 2 Control experiments
Acknowledgements
Based on the above results and previous works, the
following possible mechanism is proposed with phenyl
propargylic alcohol 1h as the example (Scheme 3). In the basic We thank the National Natural Science Foundation of China
(21502124), the “973” Project from the MOST of China
(2015CB856600), the “1000-Youth Talents Program”, the
Fundamental Research Funds for the Central Universities, the
Sichuan Provincial Department of Education (17ZA0219) and
Neijiang Normal University (KF10076) for financial support. We
also thank the comprehensive training platform of the
Specialized Laboratory in the College of Chemistry at Sichuan
University for compound testing.
reaction conditions, 1h undergoes deprotonation and then
reacts with CO2 to generate carbonate , which undergoes
I
intramolecular ring-closing reaction to form the alkylidene
cyclic carbonate intermediate 3h. Nucleophilic attack of the
carbonyl group in 3h by carbonate anion and following ring-
opening process give the intermediate II 21
Then the
.
Dieckmann-type condensation releases carbonate anion and
gives the re-cyclized product III, which is in equilibrium with
the desired tetronic acid 2h. Further deprotonation by excess
of Cs2CO3 would lead to enolate IV, which can be quenched by
acid to generate 2h. Although 1 equivalent of Cs2CO3 seems
enough for this transformation (i.e. Table 1, entry 18), excess
of Cs2CO3 (i.e. 2-4 equivalents) showed higher efficiency, which
might arise from the solubility issue of Cs2CO3 in organic
solvent or the low rate for the ring-opening process of
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6
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