Rhodium(III) Complex with a Bulky Cyclopentadienyl Ligand as a Catalyst for Regioselective Synthesis of Dihydroisoquinolones through C?H Activation of Arylhydroxamic Acids

Article abstract of DOI:10.1002/chem.201804050

Catalytic reaction of arylhydroxamic acids with alkenes represents a convenient method for preparation of biologically active dihydroisoquinolones. Here, the rhodium(III) complex [(C₅H₂tBu₂CH₂tBu)RhCl₂]₂, which allows one to carry out such reactions with high regioselectivity to obtain 4-substituted dihydroisoquinolones in 72–97 % yields, is described. The regioselectivity is provided by the bulky cyclopentadienyl ligand of the catalyst, which is formed through a [2+2+1] cyclotrimerization of tert-butylacetylene. The catalytic reaction tolerates various distant functional groups in alkenes, but is inhibited by bulky (e.g., tBu) or strongly coordinating (e.g., imidazolyl) substituents. Some of the prepared dihydroisoquinolones effectively inhibit growth of phytopathogenic fungi.

Full text of DOI:10.1002/chem.201804050

A Journal of
Accepted Article
Title: Rhodium(III) complex with a bulky cyclopentadienyl ligand as a
catalyst for regioselective synthesis of dihydroisoquinolones via
C-H activation of arylhydroxamic acids
Authors: Evgeniya A Trifonova, Nikita M Ankudinov, Maxim V Kozlov,
Mikhail Yu Sharipov, Yulia V Nelyubina, and Dmitry Perekalin
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To be cited as: Chem. Eur. J. 10.1002/chem.201804050
Link to VoR: http://dx.doi.org/10.1002/chem.201804050
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Rhodium(III) complex with a bulky cyclopentadienyl ligand as a
catalyst for regioselective synthesis of dihydroisoquinolones
via C-H activation of arylhydroxamic acids
Evgeniya A. Trifonova,[a] Nikita M. Ankudinov,[a] Maxim V. Kozlov,[b] Mikhail Yu. Sharipov,[c] Yulia V.
Nelyubina,[a] and Dmitry S. Perekalin*[a]
Abstract: Catalytic reaction of arylhydroxamic acids with alkenes
represents a convenient method for preparation of biologically active
dihydroisoquinolones. Herein we describe the rhodium(III) complex
t
t
[(C5H2 Bu2CH2 Bu)RhCl2]2, which allows one to carry out such
reactions with high regioselectivity to obtain 4-substituted dihydroiso-
quinolones in 72-97% yields. The regioselectivity is provided by the
bulky cyclopentadienyl ligand of the catalyst, which is formed by
2+2+1-cyclotrimerization of tert-butylacetylene. The catalytic reaction
tolerates various distant functional groups in alkenes, but is inhibited
by bulky (e.g. tBu) or strongly coordinating (e.g. imidazolyl)
substituents. Some of the prepared dihydroisoquinolones effectively
inhibit growth of phytopathogenic fungi.
Introduction
Rhodium(III) catalyzed CH-activation of aromatic compounds
allows one to synthesize complex heterocyclic molecules from
simple starting materials in a single step.[1] This methodology is
particularly useful for directed search for drugs candidates and
other biologically active molecules.[2,3] However, the control of
chemo- and regioselectivity of the CH-activation reactions is
often challenging.[4–8] For example, the reaction of O-pivaloyl
derivative of phenylhydroxamic acid 1 with terminal alkenes 2 in
the presence of rhodium catalyst can give two isomeric
dihydroisoquinolones 3 and 4 (Scheme 1). The classical catalyst
[(C5Me5)RhCl2]2 selectively provides 3-substituted products 3
only if styrenes, acrylic esters,[9,10] dimethylallylamine, or acrolein
diethylacetal[3] are used as alkenes.[11] Isomeric 4-substituted
dihydroisoquinolones 4 are obtained only from K[vinyl-BF3],[12]
while mixture of isomers 3 and 4 is formed in most other
cases.[9,13]
Scheme 1. General overview of the regioselectivity in Rh(III) catalyzed
synthesis of dihydroisoquinolones. More references are given in the text.
In order to gain control over the selectivity of the reaction,
various substrates and rhodium catalysts have been tested. In
particular, Corminboeuf and Cramer et al. have found that the
complex (C5Me5)Rh(OBz)2 catalyzes the formation of 4-aryl-
substituted dihydroisoquinolones 4 from O-Boc derivative of 1
(the Boc group is responsible for selectivity).[14] On the other
hand, Rovis et al. have reported that the complex
t
[(C5H3 Bu2)RhCl2]2 with the sterically-demanding cyclopenta-
dienyl ligand produces 3-alkyl-substituted dihydroisoquinolones
3 from O-pivaloyl derivative of 1 (the catalyst is responsible for
selectivity).[15] However, through the analysis of the spectra we
found that this catalyst actually produced 4-substituted
products.[16] It may be also noted that, several chiral rhodium
catalysts have been developed for enantioselective CH-
activation.[17–19] However, they have been tested mostly in
reactions of 1 with styrenes or acrylates and therefore have
produced 3-substituted dihydroisoquinolones 3.
[a]
Dr. E.A. Trifonova, A.M. Ankudinov, Dr. Y.V. Nelyubina,
Prof. Dr. D.S. Perekalin
Nesmeyanov Institute of Organoelement Compounds
Russian Academy of Sciences
Vavilova 28, Moscow, 119991, Russia
E-mail: dsp@ineos.ac.ru
[b]
[b]
Dr. M.V. Kozlov
Engelhardt Institute of Molecular Biology
Russian Academy of Sciences
Vavilova 32, Moscow, 119991, Russia
Dr. M.Yu. Sharipov
Recently we have reported the synthesis of the new chiral
t
t
rhodium catalyst [(C5H2 Bu2CH2 Bu)RhI2]2 with bulky cyclopenta-
dienyl ligand and used it for enantioselective synthesis of
dihydroisoquinolones from aryl hydroxamic acids and cyclic
alkenes.[20] Herein we report, that the closely related complex
Mendeleev University of Chemical Technology of Russia
Miusskaya sq. 9, Moscow, 125047, Russia
Supporting information for this article is given via a link at the end of
the document.
t
t
[(C5H2 Bu2CH2 Bu)RhCl2]2 (5) catalyzes the reaction of O-Boc-
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phenylhydroxamic acid 1 with terminal alkenes 2 to give 4-
substituted dihydroisoquinolones 4 with high regioselectivity
(similar to or exceeding that observed by Rovis et al.[15]). The
scope and limitations of this reaction are discussed in detail. The
anti-fungal activity of dihydroisoquinolones is also reported.
In order to put our catalyst on the scale proposed by Paton and
Rovis et al.[4] we synthesized the P(OEt)3 adduct of 5, namely
t
t
the complex (C5H2 Bu2CH2 Bu)RhCl2-P(OEt)3 (9), and measured
its 31P NMR spectrum. As expected both 31P chemical shift
(106.1 ppm) and JRh-P coupling constant (210.3 Hz) of the adduct
9 were close to the values reported for the related bis-tert-butyl-
t
substituted complex (C5H3 Bu2)RhCl2-P(OEt)3 (108.4 ppm, 206.3
Hz), as well as for the complex (C5Me4C6F5)RhCl2-P(OEt)3
(105.9 ppm, 209.4 Hz) with a bulky and mildly electron-donating
cyclopentadienyl ligand.
Results and Discussion
The
cyclopentadienyl
ligand
of
the
catalyst
t
t
[(C5H2 Bu2CH2 Bu)RhCl2]2 (5) is formed from tert-butyl acetylene
via [2+2+1]-cyclotrimerization (Scheme 2). Although this route
seems to be exotic, it has certain advantages for preparation of
complexes with multiply-substituted cyclopentadienes, which are
not easily available as free ligands. Indeed, [2+2+1]-
cyclotrimerization of alkynes has been effectively used by
Severin et al. and Tanaka et al. to obtain ruthenium[21,22] and
rhodium[23,24] complexes with sterically demanding cyclopenta-
dienyls.
The synthesis of the catalyst 5 starts from the reaction of the
readily available rhodium complex [(cod)RhCl]2 with tert-
butylacetylene in the presence of AgPF6, which gives the
cationic fulvene complex 6 (Scheme 2). This reaction has been
briefly reported almost 35 years ago, but the synthetic procedure
has not been given.[25] We found that the best yield of the
fulvene complex 6 (64%) is achieved after 1h reaction at 0 °C,
while longer reaction times diminish the yield of 6 (38% for 2h
reaction), presumably, because of the further oligomerization of
tert-butylacetylene.[26] Reaction of the cationic fulvene complex 6
with the excess of NaBH3CN gives the neutral cyclopentadienyl
complex 7. Finally, treatment of 7 with Cl2 or Br2 provides the
Figure 1. The crystal structure of the rhodium catalyst 5 in 50% thermal
ellipsoids. All hydrogen atoms are omitted for clarity. Selected distances (Å):
Rh1−Cl1 2.450(1), Rh1−Cl2 2.380(1), Rh1-C5plane 1.754.
The reaction of O-Boc-phenylhydroxamic acid (1a) with 1-
heptene (2a, 2 equiv.) smoothly proceeded at room temperature
in the presence of 2 mol-% of the catalyst 5 and gave
exclusively 4-substituted dihydroisoquinolone 4a in excellent
t
t
target catalyst [(C5H2 Bu2CH2 Bu)RhCl2]2 (5) or its bromide
t
t
analogue [(C5H2 Bu2CH2 Bu)RhBr2]2 (8) in good yields 85-90%.
The structures of the complexes 5 and 8 were confirmed by the
X-ray diffraction (Figure 1).
1
97% yield (Scheme 3). The product was identified by H-1H and
1H-13C correlation NMR spectra, as well as by the comparison of
the spectra with those of the independently synthesized 3-
substituted isomer 3a.[27] Apart from the spectral data the
formation of 4-substituted product was additionally confirmed by
the X-ray diffraction study of the related benzyl-derivative 4i
(Figure 2). Preliminary structural assignment of the isomers 3
1
and 4 can be also made from simple H NMR spectra: because
of the electron acceptor effect of the nitrogen atom the adjacent
protons have rather high chemical shift values 3.3-3.8 ppm,
while the protons adjacent to the phenyl ring have lower
chemical shifts 2.7-3.0 ppm. Therefore compounds 3 show only
one signal in 3.3−3.8 ppm region, while isomers 4 show two
such signals.
Having established the regioselectivity, we investigated the
scope of alkenes suitable for coupling with O-Boc-
phenylhydroxamic acid (1a). It was found that the reaction works
well with most aliphatic alkenes with distant functional groups
and the products 4b-m were obtained in good yields 72-97%
(Scheme 3). At the same, the catalyst was completely inhibited
by alkenes with strongly coordinating groups, such as N-vinyl-
imidazole, N-vinyl-pyrrolidone, vinyl cyanide, or vinyl methyl
sulfide.[28] Alkenes with vinyl or allyl functionalities (allyl chloride,
allyl acetate, N-Boc-allylamine, N-Ts-allylamine, isoprene, 1,3-
pentadiene, styrene, ethyl acrylate) often reacted sluggishly and
Scheme 2. Synthesis of the rhodium catalyst 5.
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produced complex mixtures of products. Bulky terminal alkenes
(tert-butylethylene, trifluoromethylethylene, vinyltriethoxysilane)
and di-substituted alkenes (3-methylene-butanol, cyclohexene,
limonene) did not react with 1a apparently because of the steric
hindrance. The exceptions were the strained di-substituted
alkenes such as cyclopentene and methylenecyclobutane, which
produced the corresponding dihydroisoquinolones 4n,o in ca.
70% yields (Scheme 4).
Figure 2. Formula and the crystal structure of the product 4i (in 50% thermal
ellipsoids), which confirms regioselectivity of the reaction. All hydrogen atoms
except NH are omitted for clarity.
Scheme 4. Catalytic reactions of O-Boc-phenylhydroxamic acid 1a with di-
substituted alkenes.
The difference in reactivity of alkenes creates the opportunity of
chemoselective reactions. For example reaction of 1a with an
equimolar mixture of allyl alcohol, styrene and myrcene proceed
selectively in the presence of the catalyst 5 to give 4-CH2OH-
substituted product 4e in 89% yield (Scheme 5). Similar reaction
in the presence of the classical catalyst [Cp*RhCl2]2 gave a
mixture of three products: Ph-substituted dihydroisoquinolone 4p,
as well as two CH2OH-substituted isomers 4e and 3e in
1.7:1:2.5 ratio (note that myrcene did not react in both cases).
In all the reactions catalyzed by the complex 5 4-substituted
dihydroisoquinolones were obtained with regioselectivity
exceeding 20:1 isomer ratio. The formation of the 4-substituted
products was surprising, since Rovis et al. had previously
t
reported that a similar catalyst [(C5H3 Bu2)RhCl2]2 provided the 3-
substituted isomers.[15] However, careful investigation of the
NMR spectra have shown that their catalyst had in fact also
provided 4-substituted dihydroisoquinolones. Other catalyst with
t
bulky cyclopentadienyl ligands such as C5Me4 Bu and C5Me3Ph2
also favor the formation of this 4-substituted products.[4]
Therefore it may be proposed that the regioselectivity in these
reactions is mainly determined by the steric repulsion between
the alkene substituent R and the bulky cyclopentadienyl ligand,
which is present in the tentative intermediate 10 and avoided in
Scheme 3. Synthesis of 4-substituted dihydroisoquinolones 4a−m. Isolated
yields are given.
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its analogue 11 (Figure 3). Regioselective formation of 3-
substituted isomers in some specific cases (e.g. in reactions of
styrenes or acrylates) is probably caused by electronic factors.
Scheme 6. Regioselectivity determined by Boc- or pivalyl group of hydroxamic
acid derivative.
We have also investigated selectivity of reactions of alkenes with
the substituted arylhydroxamic acid derivatives.[29] Previous
studies have shown that most of the functional groups (except
strong electron acceptors like NO2 or CN) in the para-position of
the hydroxamic acids do not have a significant influence.[15,20] On
the contrary, we found that ortho-bromo and ortho-methyl
substituted derivatives of 1a react with alkenes sluggishly and
tend to form corresponding anilines via Lossen rearrangement
(see similar report[3]). The meta-substituted phenylhydroxamic
acids are intriguing because they can form two regioisomeric
dihydroisoquinolones (Scheme 7). It was found, that meta-
methyl derivative 1c reacts with 1-decene in the presence of the
Scheme 5. Chemoselectivity of reaction of 1a with a mixture of alkenes.
catalyst
5 to give predominantly the expected 7-methyl-
dihydroisoquinolone 4q (77% yield, 12.5:1 rr). However, from
less hindered meta-bromo derivative 1d a mixture of 7- and 5-
substituted regioisomers 4r was obtained in 1.3:1 ratio.
Interestingly, the classical catalyst [Cp*RhCl2]2 was reported to
give only 7-substituted products in such reactions.[15]
Figure 3. Structures of possible intermediates, which explain the regio-
selectivity of insertion of alkenes. Two headed arrows show steric repulsion.
Additionally, as it was noted by Corminboeuf and Cramer et
al.,[14,17] the steric interactions between the cyclopentadienyl
ligand and the Boc group are important for selectivity. Indeed,
we observed that the reaction of O-Boc-phenylhydroxamic acid
1a with styrene in the presence of the classical catalyst
[Cp*RhCl2]2 gives only the 4-substituted dihydroisoquinolone 4p,
while similar reaction of O-pivaloyl-phenylhydroxamic acid 1b
produced the 3-substituted isomer 3p (Scheme 6). The reasons
for this striking difference are not fully clear. Unfortunately, both
reactions in the presence of the catalyst 5 proceeded slowly and
gave mixtures of products.
Scheme 7. Regioselectivity of reactions of meta-substituted derivatives of
hydroxamic acids.
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The biological activity of dihydroisoquinolones[30,31] as inhibitors Conclusions
of various enzymes is well known. However, as far as we aware,
their antifungal activity has not been investigated. Therefore we
tested the ability of 8 dihydroisoquinolones to inhibit the growth
of 6 lines of phytopathogenic fungi species (Table 1; some of the
compounds had been synthesized previously[20]). It was found
that these compounds are generally less active than the
commercial fungicides like Triadimefon and Kresoxim-methyl.
However, good inhibition activity of some lypophilic planar
dihydroisoquinolones such as 4a,b, as well as the parent
phenylhydroxamic acid makes further investigation of these
classes of compounds promising.
To conclude, we have developed the synthesis of the rhodium
t
t
catalyst [(C5H2 Bu2CH2 Bu)RhCl2]2 (5) via 2+2+1-cyclotri-
merization of tert-butylacetylene and used it for regioselective
synthesis of dihydroisoquinolones from arylhydroxamic acid
derivatives and terminal alkenes. It can be generalized that
Rh(III) catalysts with bulky cyclopentadienyl ligands favor
regioselective formation of 4-substituted dihydroisoquinolones.
We propose that the presented catalyst 5 can be used to
improve regioselectivity of other CH-activation reactions.
Table 1. Inhibition of growth of the pathogenic fungi in the presence of the
compounds (c = 30 mg L–1) expressed in %, where 100% is complete
inhibition (no growth) and 0% corresponds to the growth of the negative
control sample.
Acknowledgements
This work was supported by the Russian Science Foundation
(grant # 17-73-20144). The X-ray diffraction data were obtained
using the equipment of the Center for Molecular Composition
Studies of INEOS RAS.
V.i.[a]
R.s.[b]
F.o.[c]
F.m.[d]
B.s.[e]
S.s.[f]
Compound
Keywords: C-H activation • Rhodium • Isoquinolones •
Cyclopentadienyl ligands • Homogeneous catalysis
R = C5H11 (4a)
R = C8H17 (4b)
R = CH2Ph (4i)
26
35
27
12
42
59
31
43
29
29
26
14
26
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30
19
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33
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Entry for the Table of Contents
FULL PAPER
Evgeniya A. Trifonova, Nikita M.
Ankudinov, Maxim V. Kozlov, Mikhail
Yu. Sharipov, Yulia V. Nelyubina,
Dmitry S. Perekalin
Page No. – Page No.
Rhodium(III) complex with a bulky
cyclopentadienyl ligand as a catalyst
for regioselective synthesis of
dihydroisoquinolones via C-H
Regioselective synthesis of biologically active dihydroisoquinolones was achieved
by using rhodium(III) catalyst with bulky cyclopentadienyl ligand, which was formed
from three tert-butylacetylenes.
activation of arylhydroxamic acids
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