A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

Article abstract of DOI:10.1002/anie.202002844

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)₂ as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Full text of DOI:10.1002/anie.202002844

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Accepted Article
Title: A General Regioselective Synthesis of Alcohols by Cobalt-
Catalyzed Hydrogenation of Epoxides
Authors: Weiping Liu, Thomas Leischner, Wu Li, Kathrin Junge, and
Matthias Beller
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.202002844
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10.1002/anie.202002844
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A General Regioselective Synthesis of Alcohols by Cobalt-
Catalyzed Hydrogenation of Epoxides
Weiping Liu+,[a],[b] Thomas Leischner+,[b] Wu Li,[b] Kathrin Junge[b] and Matthias Beller*[b]
Abstract: A straightforward methodology for the synthesis of anti-
Markovnikov-type alcohols is presented. Using a specific cobalt
triphos complex in the presence of Zn(OTf)2 as additive, the
hydrogenation of epoxides proceeds with high yields and selectivities.
The described protocol shows a broad substrate scope, including
multi-substituted internal and terminal epoxides, as well as a good
functional group tolerance. Various natural product derivatives
including steroids, terpenoids and sesquiterpenoids gave access to
the corresponding alcohols in moderate to excellent yields.
rhodium- and ruthenium-based systems and suffered from poor
product selectivities.[9]
Alcohols are a class of important organic compounds, being
ubiquitous in bulk and fine chemicals as well as in natural
products.[1] Among the numerous established procedures for their
synthesis, still the classic hydroboration/oxidation protocol
starting prevails on
a
laboratory scale (Figure 1A).
Advantageously, this methodology allows for a formal anti-
Markovnikov functionalization of linear alcohols from olefins,
albeit stoichiometric amounts of borane agents have to be
employed.[2] To overcome this problem, various catalytic
approaches to provide similar products have been developed. For
example, a formal anti-Markovnikov hydration of monosubstituted
styrenes via triple relay catalysis was demonstrated by Grubbs
and co-workers.[3] More recently, Lei and co-workers established
a visible-light–mediated anti-Markovnikov hydration of water to
olefins, using a photoredox catalyst in combination with a redox-
active hydrogen atom donor.[4] Additionally, the Arnold group
realized a regioselective redox hydration of styrenes catalyzed by
a metal-oxo enzyme.[5]
Conceptually, the selective hydrogenation of epoxides, which
are readily available from alkenes by one-step oxidation using
peroxyacids or hydrogen peroxide,[6] offers an attractive
alternative (Figure 1B).[7] Heterogeneous catalysts such as Pd/C
generally facilitate this transformation but are limited to aryl
epoxides, while Markovnikov-type alcohols are formed as the
major products in case of alkyl epoxides.[8] On the contrary,
homogeneous catalysts have been scarcely investigated for this
task. Until very recently, the only known examples featured
Figure 1. Synthesis of alcohols from olefins and hydrogenation of epoxides to
alcohols.
In 2019, Gansäuer and Norton disclosed an elegant strategy
using cooperative catalysis to give linear alcohols by combining
titanocene-mediated[10] epoxide opening with chromium-
catalyzed hydrogen activation and radical reduction (Figure
1C).[11] Independently, our group developed the first non-noble
metal catalyzed hydrogenation of terminal epoxides to give
.
primary alcohols. Using a combination of Fe(BF4)2 6H2O and
tris(2-(diphenylphosphanyl)phenyl)phosphane (tetraphos) the
desired products are obtained in high yields and selectivities.[12]
However, as a drawback of this procedure only terminal epoxides
were suitable substrates, while internal epoxides did not undergo
hydrogenation to provide secondary alcohols (Figure 1D).
[a]
[b]
Dr. W. Liu
College of Chemistry, Chemical Engineering and Biotechnology,
Donghua University, 201620, Shanghai, China
Dr. W. Liu, T. Leischner, Dr. W. Li, Dr. K. Junge, Prof. Dr. M. Beller
Leibniz-Institut für Katalyse e.V.
Albert-Einstein-Straße 29a
18059 Rostock, Germany
E-mail: matthias.beller@catalysis.de
These authors contributed equally to this work.
Herein, we describe a more general and efficient non-noble
metal catalyst system[13] enabling selective hydrogenation[14] of
both internal and terminal epoxides to the corresponding alcohols
under mild conditions (Figure 1E).
[+]
Supporting information for this article is given via a link at the end of
the document.
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10.1002/anie.202002844
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main side product. [c] triphos (3.0 mol%). [d] Without triphos. [e] Zn(OTf)2
(7.0 mol%).
Based on our former studies, we explored the hydrogenation
of 2-methyl-3-phenyloxirane (1a) as benchmark substrate. As
expected, the previous Fe(BF4)2/tetraphos system gave no
significant amounts of alcohols. Similarly, in the presence of
related multidentate phosphines, e.g. 1,1,1-tris(diphenyl-
phosphinomethyl)ethane (triphos) no desired product formation
occurred. Moreover, well known molecularly-defined noble metal
complexes [Ru(acac)3/triphos][15] and [Rh(PPh3)3Cl] also failed to
furnish the desired product under otherwise identical reaction
conditions (for experimental details, see supporting information).
Other Lewis acids, such as In(OTf)3, Al(OTf)3, Fe(OTf)2
provided inferior results (Table 1, entries 6–8). Control
experiments indicated that the synergistic combination of triphos
and cobalt precursor is crucial for the epoxide hydrogenation
process (Table 1, entries 9 and 10). Increasing the amount of
additive, further improved the obtained yield of 2a to 85% (Table
1, entry 11). In general, other cobalt precursors can be applied in
this benchmark process but resulted in slightly lower catalyst
activities (Table 1, entries 12 and 13). It should be noted that
standard heterogeneous catalysts, such as PtO2, Pd/C and
Raney-Ni exhibited significantly lower or even no activity, even in
the presence of Zn(OTf)2 (for experimental details, see supporting
information).
To understand whether the cobalt or zinc salts catalyze the
isomerization of epoxides to the corresponding ketone, several
control experiments were conducted (see supporting information).
Interestingly, the Meinwald-rearrangement of 1a to 2a´ also
proceeded without co-catalyst; however, addition of Zn(OTf)2
improved this reaction step.
With optimized reaction conditions in hand, we tested the
suitability of our methodology towards various internal epoxides.
As shown in Scheme 1, various di- and tri-substituted internal
epoxides, were successfully applied and yielded the desired
secondary alcohols in good yields and high regioselectivities. All
the reactions occurred under relatively mild conditions and
importantly, tolerate a variety of valuable substituents and
functional groups irrespective of their location at the ortho-, meta-
or para-position. Notably, ester 2q, which is typically reduced by
cobalt/triphos catalysts, remained unaffected under the applied
conditions and led to the corresponding alcohol in 74% yield
(Scheme 1).[13a] In addition, chiral dialkyl-substituted internal
epoxides 2k, 2m and 2r were successfully transformed to
diastereomeric secondary alcohols.
.
Interestingly, applying the combination of Co(BF4)2 6H2O and
tetraphos in the presence of HNTf2 the desired anti-Markovnikov
type product 1-phenylpropan-2-ol (2a) was obtained, albeit in a
low yield (17%), alongside with 1-phenylpropan-2-one (2a’) as
side product (for experimental details, see supporting information).
When triphos was tested as ligand, a slight increase in activity
was observed (Table 1, entry 1). Changing the catalyst precursor
to Co(NTf2)2, further improved the observed yield (Table 1, entry
2); however when the reaction temperature was decreased
(100 oC), the hydrogenation process almost completely stopped
and only minor amounts of 2a could be detected (Table 1, entry
3). Notably, the addition of catalytic amounts of Zn(OTf)2
(3.0 mol%) significantly improved catalyst activity, even at lower
temperature (80 oC) (Table 1, entries 4 and 5).
Table 1. Optimization of Cobalt-Catalyzed Hydrogenation of Epoxide (1a)[a]
Entry
Catalyst
Additive]
T (oC)
2a (%)[b]
1[c]
2[c]
3
Co(BF4)2 6H2O
HNTf2
---
120
120
100
100
80
23
43
<10
74
80
74
<10
18
---
.
Co(NTf2)2
Co(NTf2)2
Co(NTf2)2
Co(NTf2)2
Co(NTf2)2
Co(NTf2)2
Co(NTf2)2
---
---
4
Zn(OTf)2
Zn(OTf)2
In(OTf)3
Al(OTf)3
Fe(OTf)2
Zn(OTf)2
Zn(OTf)2
Zn(OTf)2
Zn(OTf)2
Zn(OTf)2
5
6
80
7
80
8
80
9
80
10[d]
11[e]
12[e]
13[e]
Co(NTf2)2
Co(NTf2)2
80
---
80
85
80
73
.
Co(BF4)2 6H2O
80
.
Co(ClO4)2 6H2O
80
[a] Reaction conditions: 1a (0.5 mmol), [Co] (3.0 mol%), triphos (6.0 mol%),
additive (3.0 mol%), THF (4 mL), 16 h, yields were determined by GC using
n-hexadecane as internal standard. [b] 1-Phenylpropan-2-one 2a´ is the
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Scheme 1. Cobalt-catalyzed hydrogenation of internal epoxides. Reaction
condition: 1 (0.5 mmol), Co(NTf2)2 (3.0 mol%), triphos (6.0 mol%), Zn(OTf)2 (7.0
mol%), THF, 80 °C, 16 h. [a] The diastereoisomer ratio is 1:1.1. [b]
Co(BF4)2.6H2O (3.0 mol%), 1,4-dioxane, 60 °C, 20 h, the diastereoisomer ratio
(2.8:1) and yield were determined by GC.
determined by GC using n-hexadecane as internal standard. [c] Co(NTf2)2 (3.0
mol%), Zn(OTf)2 (7.0 mol%). [d] The major isomers are showing here. TBS = t-
Butyldimethylsilyl.
Additionally, the bio-active pentacyclic triterpenoid Betulin (3k),
which is abundant in the bark of birch trees and moreover plays
an active role in antiviral, analgesic and antineoplastic agents,
furnished the hydrogenated products in good yields too. Similarly,
pregnenolone (3j), an important steroid, underwent the
hydrogenation process smoothly, providing the diastereomeric
alcohols in 77% isolated yield.
However, when the tetra-substituted epoxide 2,2,3,3-
tetramethyloxirane 1s (see supporting information) was applied to
our reaction conditions, only formation of a complex product
mixture was observed.
The applied cobalt-based catalyst system is not restricted to the
hydrogenation of internal oxiranes. In fact, numerous terminal
epoxides, including several natural product derivatives (steroids,
terpenoids and sesquiterpenoids), were effectively hydrogenated
to the linear alcohols with high regioselectivities. Compared to our
previously disclosed iron/tetraphos catalyst system, the
cobalt/triphos catalyst demonstrated a wider applicability for such
substrates, too (Scheme 2).[12] More specifically, both mono- and
di-substituted terminal epoxides were suitable substrates and
provided the desired anti-Markovnikov type alcohols in good
yields tolerating amide, silyloxy, alkene and ester substituents.
Using renewable terpenes, such as (±)-camphene (3g), (-)-β-
pinene (3h) and (+)-aromadendrene (3i), which are the main
constituent of essential oil, the respective primary alcohols were
isolated in high yields and selectivities.
To better understand the strong performance of our
cobalt/triphos catalyst, a set of mechanistic experiments was
carried out. Firstly, kinetic studies using the model substrate 2-
methyl-3-phenyloxirane (1a) were performed. As shown in
Scheme 3a, 1a is quickly isomerized[16] to 1-phenylpropan-2-one
(2a’), followed by subsequent hydrogenation to the desired
alcohol 2a.[17] To further prove that 2a’ indeed is a reaction
intermediate, a control experiment employing 1a as starting
material under an argon atmosphere without hydrogen present
was conducted. Accordingly, 1-phenylpropan-2-one (2a’) was
isolated in almost quantitative yield. Next, 2a’ was used as
substrate under the standard reaction conditions, yielding the
corresponding hydrogenation product 2a in 92% yield (Scheme
3b). In agreement with these observations, [D]2-2a was obtained
as the final product in a deuterium labelling experiment applying
D2 instead of H2 (Scheme 3c). Based on all these results, we
propose, that the reaction takes place via Meinwald
rearrangement of the epoxide to the corresponding carbonyl
compound, followed by subsequent cobalt/triphos-catalyzed
hydrogenation to the desired anti-Markovnikov alcohols.
Scheme 3. Selected mechanistic studies.
In summary, the first cobalt-catalyzed hydrogenation of
epoxides for the synthesis of anti-Markovnikov alcohols is
reported. The presented methodology is suitable for internal as
well as terminal epoxides and works smoothly even with multi-
substituted derivatives under mild conditions. This novel cascade
transformation is well-suited for reduction of natural product-
derived epoxides, including steroids, terpenoids and
sesquiterpenoids. Mechanistic studies indicate that initially a
Meinwald rearrangement of the epoxides to the corresponding
Scheme 2. Cobalt-catalyzed hydrogenation of terminal epoxides. Reaction
condition: 3 (0.5 mmol), Co(BF4)2.6H2O (3.0 mol%), triphos (6.0 mol%), 1,4-
dioxane (6 mL), 80 °C, 16 h. [a] THF (4 mL) as solvent. [b] Yields were
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attractive
alternative
compared
to
the
traditional
hydroboration/oxidation protocol of olefins.
Acknowledgements
We thank the analytic department (LIKAT) for their support, the
State of Mecklenburg-Western Pomerania, the Federal State of
Germany (BMBF) and the EU (Grant 670986) for financial support.
Keywords: cobalt • homogeneous catalysis • hydrogenation •
anti-markovnikov • epoxides • alcohols • triphos
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This article is protected by copyright. All rights reserved.

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COMMUNICATION
Weiping Liu+, Thomas Leischner+, Wu
Li, Kathrin Junge and Matthias Beller*
Page No. – Page No.
A General Regioselective Synthesis
of Alcohols by Cobalt-Catalyzed
Hydrogenation of Epoxides
Text for Table of Contents
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