CuCl-Promoted β‑Acylation of Cyclopropanols with Thioesters
Savva Ponomarev, Sandra W. Papinśka, Michael Stier, Johannes Kästner, and Ivana Fleischer*

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ABSTRACT: CuCl-induced cyclopropyl alcohol ring-opening followed by β-
acylation with thioester is reported. Cyclopropanols and thioesters with various
substitution patterns were successfully subjected to the reaction, and a series of
1,4-dicarbonyl compounds were synthesized. The mechanistic investigation
revealed the involvement of Cu(I)-homoenolate, which reacts with the thioester
via oxidative addition. Both experimental and computational evidence were
found. Operational simplicity, high chemo- and regioselectivity, and good to
excellent yields are the core features of the presented approach.

Cyclopropanols and their derivatives are synthetically
useful compounds since they easily undergo various

ring-opening processes due to ring strain. Their general
advantage is that under certain conditions, they can generate
nucleophilic as well as electrophilic intermediates or radicals
(Scheme 1A), which opens the way to a wide spectrum of

transformations, including couplings.1 An example of the
generation of electrophilic intermediates is the Ni-catalyzed
arylation of cyclopropyl tosylates with arylboronic acids,
reported by Rousseaux and co-workers.2 Many valuable
developments have been made in the field of radical reactions
of cyclopropanols. Oxidation of the hydroxy group leads to an
oxygen-centered radical, which is unstable and readily
rearranges into a linear carbon-centered β-keto radical.3 The
latter can directly attack radical acceptors4 or be coupled with
another radical using transition metal catalysis.5

The functionalization of cyclopropanols via formation of
nucleophilic metal homoenolate is a rapidly advancing area of
research.6 This activation gives access to modification of the β-
carbon atom with a diverse range of electrophiles. Numerous
reports disclose allylation, propargylation, and alkynylation
procedures via sequential cyclopropanol activation with
organozinc and -copper reagents.7 Benzyl chlorides as well as
N-hydroxyphtalimides were found to be suitable for catalytic β-

alkylation of cyclopropyl alcohols.8 Installation of a trifluoro-
methyl group was achieved with usage of Togni reagent and
Cu(I) catalyst.9 However, the authors claimed that the reaction
may proceed via both nucleophilic and radical intermediates.
Employment of palladium as catalyst enabled β-arylation with
aryl halides and triflates.10 Moreover, several techniques for
metal homoenolate β-acylation have been developed (Scheme
1B).11 The generated 1,4-dicarbonyl functionality can be found
in several bioactive molecules, and it represents a valuable
building block in the synthesis of various heterocycles.12

In 2013, Cha and co-workers published Pd-catalyzed
acylation of 1-alkyl- and 1-benzyl-substituted cyclopropanols.13

A stoichiometric amount of Et2Zn was used to generate the
corresponding zinc homoenolates, which reacted with acyl
chlorides in the presence of Pd(PPh3)4. The authors did not
comment on the mechanism, but without the Pd catalyst, only
acylation of the cyclopropoxide took place. Interestingly, no
organometallic reagent was needed in the more recently
reported Pd-catalyzed acylation using activated amides.14 In
this work, we report another convenient way to obtain 1,4-
diones through copper homoenolate intermediates acylated by
S-phenyl-substituted thioesters (Scheme 1B), which are easily
accessible via known procedures starting from different
compound classes.15 Thioesters are benchtop-stable alternative
electrophiles to acyl chlorides, and they have been employed in
various coupling reactions.16

Initially, we applied the reported conditions for acyl
chlorides employing Pd(II)-catalyst and Zn2Et to achieve the
desired thioester coupling,13 but low regioselectivity and
unsatisfactory yields were observed. Omitting Et2Zn proved

Received: February 3, 2026
Revised: February 27, 2026
Accepted: March 4, 2026
Published: March 10, 2026

Scheme 1. Cyclopropanol-Derived Intermediates (A),
Synthesis of 1,4-Diones from Cyclopropanols (B)

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completely inefficient, in contrast to coupling of activated
amides.14 Considering the higher reactivity of copper
homoenolate in comparison with zinc,7a we decided to activate
the substrate with a combination of CuCl and a base instead of
Et2Zn, which turned out to be the key move in the
optimization process (for more details, see the SI). The
optimized conditions (1.5 equiv. CuCl, 1 equiv. K2CO3, in
acetonitrile at 80−90 °C overnight) were applied to coupling
of a broad scope of cyclopropanols and thioesters to obtain 30
products in 48 to 91% yields (Scheme 2A and 2B). 1-Alkyl-

substituted and both electron-rich and -deficient 1-aryl-
substituted cyclopropyl alcohols were successfully converted
into corresponding 1,4-diones 3aa-3la. Functional groups like
ether, protected amines, and conjugated double bond tolerated
the developed conditions. 1,2-Disubstituted cyclopropyl
alcohols regioselectively formed products via cleavage of the
less substituted bond of the three-membered ring (3oa-sa).
Among the tested thioesters, aromatic compounds with diverse
substitution patterns furnished products 3ab-ai in good yields.
Alkyl- and alkenyl-substituted thioesters also performed well,

Scheme 2. Scope of the Copper-Mediated Coupling of Cyclopropanols (A) and Thioesters (B)a

aReaction conditions: 1 (1.0 mmol), 2 (1.5 mmol), CuCl (1.5 mmol), and K2CO3 (1.0 mmol) are mixed in MeCN (0.1 M) and heated overnight
(ON) to 80 °C under Ar. Isolated yields. b90 °C.

Scheme 3. Possible Reaction Pathways of Cyclopropanol Ring-Opening (A) and Determination of Active Intermediate (B−
E)a

aThe yields are calculated via 1H NMR using 1,3,5-trimethoxybenzene as internal standard, unless otherwise specified. bCuCl (1.5 equiv) and
K2CO3 (1.0 equiv) in MeCN (0.1 M) at 80 °C overnight. cIsolated yield.

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and the products 3aj-3al were obtained in 75−88% yields. It
should be mentioned that the system has limitations: aryl
iodides are prone to dehalogenation, and ortho-substituted 1-
aryl-cyclopropanols were not fully converted even at 90 °C
(see SI, Scheme S1). Nonetheless, the reaction shows high
versatility: almost 70% of products were obtained in 80% yield
or higher. Additionally, other electrophiles were tested under
designed conditions (SI, Scheme S2). More reactive acyl
chlorides, S-pyridyl-thioesters, as well as less electrophilic S-
alkyl-substituted thioesters showed noticeably lower efficiency.
Cyclohexenone was completely unreactive, while allyl bromide
gave 79% of the coupling product.

Copper catalysis and mediation are broadly used tools in
cyclopropyl alcohol chemistry, mainly due to the ability of
copper to form several types of functional intermediates. Their
nature, in general, depends on the oxidation state of copper
(Scheme 3). Copper(I) forms Cu(I)-homoenolates A via β-C

elimination, and copper(II) furnishes β-keto radicals C via a
redox process. Copper(II) can also lead to Cu(II)-
homoenolates B, but they are usually unstable and readily
decompose into the aforementioned β-keto radicals C and
copper(I).6 At the same time, copper(I) can disproportionate
under certain conditions and form copper(II).17 Thus,
regardless of the initial oxidation state of copper, copper
species with a different oxidation state might be operational in
the target reaction. Hypothetically, all three types of
intermediates can react with the thioester, leading to 1,4-
diketone product (see SI for more details). Cu(I)- and Cu(II)-
homoenolates A and B can react with the thioester via
conventional nucleophilic 1,2-addition. Cu(I)-homoenolate A
can also be engaged in the oxidative addition process. The β-
keto radical C can attack the carbonyl group of the thioester
(see SI), since thioesters are known as radical acceptors.18 A
distinctive feature of the ionic vs radical pathway is the

Scheme 4. Investigations of Possible Pathways Including Cu(I)-Homoenolate Intermediatea

aThe yields are calculated via 1H NMR or GC FID using internal standards. bCuCl (1.5 equiv) and K2CO3 (1.0 equiv) in MeCN (0.1 M) at 80 °C
overnight.

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regioselectivity of the ring-opening of 1,2-disubstituted cyclo-
propyl alcohols (Scheme 3a). While the radical C−C bond
cleavage occurs at the more substituted bond, the ionic β-C
elimination leads to sterically less hindered metal homoeno-
late.6

A series of experiments were performed to differentiate
between the radical and ionic mechanism. The EPR spectrum
of the reaction mixture did not reveal any signals, which
testifies to the absence of paramagnetic species in the reaction
(Scheme 3B). The coupling of 2-cyclopropyl-substituted
substrate 1r with 2a led to the diketone 3ra with a retained
cyclopropyl substituent in 86% yield. No product 4, which
would be expected in the case of radical ring-opening, was
detected (Scheme 3C). Similarly, the allyl-substituted cyclo-
propyl alcohol 1t did not furnish any of the possible products
of radical cyclization 5 and/or 6 (Scheme 3C). Furthermore,
reactions in the presence of radical scavengers were conducted.
While BHT (2,6-di-tert-butyl-4-methylphenol) and PBN (N-
tert-butyl-α-phenylnitrone) did not influence the product
formation, no target diketone 3aa was observed when
TEMPO was used (Scheme 3D). However, it was shown
that TEMPO oxidizes cyclopropanol 1a into the enone 7 via C
(Scheme 3D).19 Therefore, the total suppression of 3aa
formation in the presence of TEMPO shows that neither C nor
7 are viable intermediates in the reaction. When CuCl was
replaced with CuCl2, the reaction showed significantly lower
efficiency, as only 19% of 3aa was obtained, and the vinyl
ketone 7 was formed as the main product (Scheme 3E).
Generally, CuCl2 could lead to intermediates B or C, but the
low yield of 3aa testifies against engagement of these
intermediates in product formation. Cu(I) species generated
in the oxidation of 1a by Cu(II) could still be involved in the
reaction via Cu(I)-homoenolate A (Scheme 3A). To
summarize, the results of all conducted tests point against
the participation of any paramagnetic species (organic radicals
and Cu(II) species). Therefore, the reaction most likely
proceeds via Cu(I)-homoenolate A (Scheme 3A).

This intermediate can further react with the thioester via 1,2-
addition or oxidative addition. DFT computations were
performed using ORCA,20 version 6.0.1, with the ChemShell21

interface to differentiate between these pathways.22 Geometry
optimizations and frequency calculations were performed with
the ωB97X-3c23 composite method. Single point calculations
were performed on the ωB97M-V/def2-QZVPP24 level of
theory in combination with the SMD solvation model25 for
acetonitrile. Gibbs free energies were computed within the
rigid-rotor harmonic-oscillator approximation. More computa-
tional details and all geometries are given in the SI. Their
Gibbs free energy profile along with the corresponding
structures are depicted in Scheme 4A. The formation of the
precomplex, as well as the release of the final product, were not
considered, as these reactions might involve solvent molecules
or counterions. It remains unclear what the exact species in the
corresponding solvent are, making computation impossible.
Both identified precomplexes exhibit similar stability. However,
the activation barrier for the nucleophilic addition pathway is
relatively high (119 kJ mol−1), making this pathway unlikely.
Consequently, the nucleophilic addition route was not further
considered. In contrast, the activation barrier for the oxidative
addition pathway is 26 kJ mol−1, indicating that this is the
preferred reaction mechanism. This barrier corresponds to the
rate-determining step. The subsequent intermediate is slightly
more stable than the precomplex. Formation of the final

complex from this intermediate is barrierless and highly
exergonic (155 kJ mol−1), effectively preventing back-reactions.

The experimental confirmation of these results proved
difficult, since it was not possible to detect any intermediates
spectroscopically. Based on the kinetic investigation (see SI),
which showed that the maximal reaction rate is reached
between 2−20 min, we decided to find indirect evidence for
intermediates within this time by freezing the standard reaction
after 10 min using liquid N2 (Scheme 4B). The analysis with
GCMS and 1H NMR revealed the formation of β-keto sulfide
8a, which was not detected under standard conditions. This
compound could be formed via conjugate 1,4-addition of a
thiolate to enone 7a (eventual product of β-H elimination
from 1a) or via alternative reductive elimination from Cu(III)-
complex D (Scheme 4B). To test the feasibility of 1,4-addition
of a thiolate to 7a, a series of control experiments was carried
out (Scheme 4C). The direct reaction of enone 7a with 2a
under standard conditions did not furnish product 8a. Thus,
the thioester is not a source of thiolate, which would react with
7a. Furthermore, we performed a competition experiment
using cyclopropyl alcohol 1a and enone 7b containing different
aryl groups. Under standard conditions, only expected
coupling product 3aa formed. Upon cooling, also β-keto
sulfide 8a was observed, but no sulfide 8b generated from the
enone. This confirms that β-keto sulfide cannot be formed
through 1,4-addition of thiolate to enone but rather through
reductive elimination from Cu(III)-complex D (Scheme 4D).
This process seems to be suppressed at higher temperatures.
Furthermore, we observed the formation of diphenylsulfide,
which could be generated via a decarbonylation process from
D, which additionally supports this pathway.

Based on the collected data, the following mechanism can be
proposed (Scheme 5). Under basic conditions, cyclopropanol

1 is converted into cyclopropanolate G, which furnishes the
homoenolate A through β-C elimination. Subsequently, A
reacts with thioester 2 via oxidative addition providing D,
which undergoes reductive elimination yielding product 3.
Cu(I) turnover is not possible due to the precipitation of
CuSPh.

In summary, we developed a novel approach to β-acylation
of cyclopropyl alcohols via in situ generated Cu(I)-
homoenolate using thioesters as the acyl source. Mechanistic
investigations point toward the ionic pathway proceeding

Scheme 5. Plausible Reaction Mechanism

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through the Cu(I) homoenolate intermediate, which reacts
with thioester via oxidative addition.

■ ASSOCIATED CONTENT
Data Availability Statement
The data underlying this study are available in the published
article and its Supporting Information.
*sı Supporting Information
The Supporting Information is available free of charge at
https://pubs.acs.org/doi/10.1021/acs.orglett.6c00432.

Text file of all computed molecule Cartesian coordinates
in a format for convenient visualization (XYZ)
Experimental details, compound characterization data
and NMR spectra (PDF)
Text file of all computed molecule Cartesian coordinates
in a format for convenient visualization (XYZ)

■ AUTHOR INFORMATION
Corresponding Author

Ivana Fleischer − Institute of Organic Chemistry, Faculty of
Science, Eberhard Karls Universität Tübingen, 72076
Tübingen, Germany; orcid.org/0000-0002-2609-6536;
Email: ivana.fleischer@uni-tuebingen.de

Authors
Savva Ponomarev − Institute of Organic Chemistry, Faculty of
Science, Eberhard Karls Universität Tübingen, 72076
Tübingen, Germany

Sandra W. Papińska − Institute of Organic Chemistry, Faculty
of Science, Eberhard Karls Universität Tübingen, 72076
Tübingen, Germany

Michael Stier − Institute for Theoretical Chemistry, University
of Stuttgart, Stuttgart 70569, Germany; orcid.org/0009-
0003-8810-5324

Johannes Kästner − Institute for Theoretical Chemistry,
University of Stuttgart, Stuttgart 70569, Germany;
orcid.org/0000-0001-6178-7669

Complete contact information is available at:
https://pubs.acs.org/10.1021/acs.orglett.6c00432

Author Contributions
The manuscript was written through contributions of all
authors. All authors have given approval to the final version of
the manuscript.
Notes
The authors declare no competing financial interest.

■ ACKNOWLEDGMENTS
The authors thank the NMR and MS facilities of the Institute
of Organic Chemistry at the University of Tübingen for their
excellent analytical service. We are grateful to University of
Tübingen for the financial support. Michael Stier acknowledges
financial support received in the form of a Ph.D. scholarship
from the Studienstiftung des Deutschen Volkes (German
National Academic Foundation). The authors acknowledge
support from the state of Baden-Württemberg through
bwHPC and the German Research Foundation (DFG)
through Grant No. INST 40/575-1 FUGG (JUSTUS2
cluster).

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