A Visible-Light-Induced Strategy To Construct Osmanaphthalynes, Osmaanthracyne, and Osmaphenanthryne

Article abstract of DOI:10.1002/chem.201803576

Herein, we describe a novel, green, and efficient synthesis of a series of different substituted osmanaphthalynes (including -H, -Br, -I, -CH₃ and -CF₃) and the first examples of the preparation of α-osmaanthracyne and α-osmaphenanthryne by means of a visible light-induced intramolecular cyclization reaction of their corresponding osmium hydrido alkenylcarbyne complexes. This visible-light-driven method provides an efficient and straightforward approach to afford the desired fused metal heterocyclic complexes constructed with an Os atom as the metal center in high yield under mild conditions.

Full text of DOI:10.1002/chem.201803576

A Journal of
Accepted Article
Title: A Visible Light-Induced Strategy to Construct Osmanaphthalynes,
Osmaanthracyne and Osmaphenanthryne
Authors: Shenghua Liu, Ming-Xing Zhang, Zhiqiang Xu, Tao Lu, and
Jun Yin
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To be cited as: Chem. Eur. J. 10.1002/chem.201803576
Link to VoR: http://dx.doi.org/10.1002/chem.201803576
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A Visible Light-Induced Strategy to Construct Osmanaphthalynes,
Osmaanthracyne and Osmaphenanthryne
Ming-Xing Zhang,[a] Zhiqiang Xu,[a] Tao Lu,[a] Jun Yin*[a] and Sheng Hua Liu*[a], [b]
Dedication ((optional))
Abstract: Herein, we describe a novel, green and efficient synthesis
of a series of different substituted osmanaphthalynes (including −H,
−Br, −I, −CH3 and −CF3) and the first examples of the preparation of
α-osmaanthracyne and α-osmaphenanthryne by means of a visible
which are both osmanaphthalynes. In 2007, Jia et al.
synthesized the first metalnaphthalyne, compound A, via the
reduction of an osmium carbyne complex using zinc powder and
light-induced
intramolecular
cyclization
reaction
of
their
corresponding osmium hydrido alkenylcarbyne complexes. This
visible-light-driven method provides an efficient and straightforward
approach to afford the desired fused metal heterocyclic complexes
constructed with an Os atom as the metal center in high yield under
mild conditions.
In 1979 Thorn and Hoffmann predicted the existence of three
types of transition metal heterocyclic complexes on the basis of
the “Hückel molecular orbital method” and thus proposed a new
concept for transition metal heterocyclic complexes.1 When
compared with main group elements, transition metals not only
possess more types and valence states, but also possess d- and
s-orbitals. Therefore, transition metal heterocyclic complexes
have the characteristics of both organometallic compounds and
fused organic compounds; therefore they have increased
properties and performance. These advantages provide
transition metal heterocyclic complexes with more room for
development in the design and application of molecular
structures.
Over the past 30 years, research on metal heterocyclic
compounds has made great achievements, metal heterocyclic
chemistry has been flourishing and a series of metal heterocyclic
complexes have been reported. A variety of transition metals,
such as Os, Ir, Ru, Re, Nb, Ta, Mo, W, Ni and Pt have been
used in the construction of transition metal heterocyclic
complexes.2 The vigorous development of these transition metal
heterocyclic complexes not only includes the choice of transition
metal atom, but also the various types of fused metal
Scheme 1. Synthetic routes of the first and second examples of the
metalnaphthalynes (A and B) and the first examples of metallaanthracene and
derived metallaanthraquinone compounds (C and D).
subsequent C−Cl bond activation (Scheme 1a).7a Two years
later, Xia's research team investigated the reactivity of the
osmium hydrido alkenylcarbyne complex and found that it can
be heated to 120°C in its solid-state under an oxygen
atmosphere through C–H activation to produce an
osmanaphthalyne B, which is similar to osmanaphthalyne A
(Scheme 1b). In addition, osmanaphthalyne B can also be
prepared by reacting a binuclear osmanaphthalene compound
with acid and triphenylphosphine under an air atmosphere.7b In
addition, Wright et al. successfully designed and synthesized
iridaanthracene C and iridaanthraquinone D in 2016 (Scheme
1c).8 This is the first example of an metallaanthracene and its
metallaanthraquinone derivative. These results add new
members to the metal heterocyclic complex family and provide
new methods and strategies for the design and synthesis of
more fused metal heterocyclic complexes.
heterocyclic
compounds,
such
as
metallabenzene,3
metallafuran,4
metallabenzyne,5
metallanaphthalene,6
metallanaphthalyne,7 metallaanthracene,8 metallapentalynes,
metallapentalenes and their derivatives.9 Among these metal
heterocyclic compounds, osmium-containing complexes are the
most studied.
Metalnaphthalynes are a very rare type of fused metal
heterocyclic complex, with only two cases reported to date,
The amount and type of osmium heterocyclic complexes
are relatively small. The scarcity of a common and mild
synthesis method has limited the compounds reported to date to
simple monocyclic systems such as osmabenzenes,3
[a]
[b]
M. X. Zhang, Z. Xu, T. Lu, Prof. J. Yin, Prof. S. H. Liu
Key Laboratory of Pesticide and Chemical Biology, Ministry of
Education, College of Chemistry, Central China Normal University,
Wuhan 430079, P. R. China
E-mail: yinj@mail.ccnu.edu.cn; chshliu@mail.ccnu.edu.cn
Prof. S. H. Liu
osmaphenols and osmabenzynes.5 However,
osmium
heterocyclic fused ring species such as osmapentalynes,
osmapentalenes,9 osmatricycles8 are relatively rare. The lack of
common and mild synthesis method not only limits the types of
these metal heterocyclic compounds, but also limits the further
exploration of their rich properties. Therefore, new methods for
studying the synthesis of metal heterocyclic complexes are still a
State Key Laboratory of Structural Chemistry, Fujian Institute of
Research on the Structure of Matter, Chinese Academy of Sciences,
Fuzhou 350002, P. R. China
Supporting information for this article is given via a link at the end of
the document.
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challenging topic and it is of great significance to develop new
synthetic methods or to synthesize new kinds of transition metal
heterocyclic complexes. Over the past few decades, visible-light-
induced methods have attracted increasing interest for reactivity
engineering and reaction design due to their inherent green
chemistry and sustainable features. This green approach has
been successfully applied to construct a wide range of valuable
organic molecules, but it′s application in general metal
complexes is still relatively rare,10 let alone metal heterocyclic
compounds where the metal is a heteroatom.
and C=C bonds, without any obvious bond length alternation,
thus demonstrating that the compounds 2b–2e delocalized
structures.
Here we report an efficient and straightforward approach to
afford the desired fused heterocyclic complexes constructed with
Os atoms as the metal center in high yields under mild
conditions. To our knowledge, our visible light-induced synthesis
method is the first example of this method applied to the
synthesis of fused metal heterocyclic compounds.
Initially, based on its UV absorption (Figure S1), we tested
the feasibility of this visible light-induced intramolecular
cyclization reaction with osmium hydrido alkenylcarbyne
complex 1a in CHCl3 under 7 W blue LED (450−460 nm)
irradiation for 3.5 h at room temperature without the protection of
a nitrogen atmosphere. To our delight, the intramolecular
cyclization reaction proceeded smoothly to obtain the desired
product, osmanaphthalyne 2a, in high yield (Scheme 2). To
further demonstrate the synthetic utility of this method under the
standard reaction conditions, a series of different substituted
osmium hydrido alkenylcarbyne complexes (−H, −Br, −I, −CH3,
−CF3) were used (Scheme 2). According to the experimental
results, this type of visible light-induced synthesis method can
be successfully applied to the synthesis of osmanaphthalynes
(2a–2e) and the osmium hydrido alkenylcarbyne complexes
(1a–1e) bearing different substituents can be converted into the
target products within 2–4 h in high yield (ca. 80%).
Figure 1. X-ray crystal structure of 2b shown with thermal ellipsoids at the
−
50% probability level. The anion BF4 and hydrogen atoms are omitted for
clarity.
Inspired by these results, we were eager to verify if this
novel visible light-induced method was efficient for the synthesis
of larger fused osmium heterocyclic systems, which, if
successful, would provide expeditious access to valuable
diversely fused metal heterocyclic systems. Therefore, we
expanded the osmium hydrido alkenylcarbyne complex from
[OsH{C≡C(PPh3)=CHPh}(PPh3)2Cl2]BF4(1a)
to
[OsH{C≡C(PPh3)=CH(α-naphthyl)}(PPh3)2Cl2]BF4
(3a)
and
[OsH{C≡C(PPh3)=CH(β-naphthyl)}(PPh3)2Cl2]BF4 (3b). Excitingly,
we successfully obtained the first examples of an α-
osmaanthracyne with a one-dimensional structure and two-
dimensional α-osmaphenanthryne (Scheme 3). Through
monitoring the experimental process, α-naphthyl-substituted
osmium hydrido alkenylcarbyne complex (3a) can completely
react within 4h. However, the β-naphthyl-substituted osmium
hydrido alkenylcarbyne complex (3b) only needs around 2 h to
react completely. This difference was most likely due to the
different dihedral angle (62.16° for 3a and 20.25° for 3b)
between the plane of the naphthalene ring and the plane where
the Os≡C bond is located (Figures S7 and S8, and Tables S4,
S12 and S13). The larger twist within 3a may inhibit the
intramolecular cyclization, resulting in a relatively slow reaction
speed. The yields of these two complexes were as high as 72%
and 75%, respectively. Besides, complexes 4a and 4b are
thermally stable in both the solid-state and solution.
Scheme 2. Synthesis routes of a series of osmanaphthalynes (2a–2e) with
different substituents (−H, −Br, −I, −CH3, −CF3).
In addition to nuclear magnetic resonance (NMR)
spectroscopy, high-resolution mass spectrometry (HRMS), and
elemental analysis, the structure of the –Br and –I substituted
osmium hydrido alkenylcarbyne complexes (1b and 1c) and
osmanaphthalynes (2b, 2c, 2d and 2e) were also confirmed with
X-ray diffraction (Figure 1, Figures S2–S6). The corresponding
crystallographic details are listed in Tables S1–S3 and selected
bonds distances and angles for these compounds are listed in
Tables S6–S11. The X-ray structural analysis shows complexes
2b–2e have an essentially planar metallacycle, which is similar
to the structure of compound 2a previously reported by the Xia
group.11 The bond lengths of Os≡C and other related
parameters are in line with the data already reported in the
literature (Table 1).12 The C−C bond lengths in the metallacycle
of these complexes are basically between that found for C−C
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Scheme 3. Synthetic routes of α-osmaanthracyne (4a) and α-
osmaphenanthryne (4b).
degree of intramolecular distortion in compounds 3a and 3b,
which was mentioned beforehand.
Table 1. The comparison of selected bond distances (Å) and angles (°) of
compounds 2b–2e, 4a and 4b.
Complexes
Os≡C
Os–C1–C2
2a7b
1.732(4)
1.733(6)
1.729(8)
1.735(9)
1.737(5)
1.795(11)
1.712(12)
1.754(7)
1.69–1.84
155.0(3)
152.0(5)
2b (-Br)
2c (-I)
2d (-CH3)
2e (-CF3)
4a
152.8(6)
152.2(7)
152.2(4)
148.8(9)
4b
153.8(9)
A7a
151.1(5)
Ref.12
148.3(6)–154.9(9)
Figure 2. X-ray crystal structure of 4a shown with thermal ellipsoids at the
−
50% probability level. The anion BF4 and hydrogen atoms are omitted for
clarity.
Labeling scheme:
Finally, we tried to explore the possible mechanism of this
type of visible light-induced intramolecular cyclization reaction.
By using the reported compound 1a as a representative
example, we carried out six parallel experiments under the same
basic conditions and monitored the experimental results using
31P NMR spectroscopy (Figure 4). Initially, to verify the necessity
of light (blue LED) for these reactions, we performed
experiments 1 and 6, in which compound 1a was dissolved in
chloroform and stirred for 3.5 h at room temperature with or
without 7 W blue LED irradiation, respectively. As it can be seen
from the 31P stacked spectra, in experiment 6, in which
compound 1a was stirred at room temperature for 3.5 h without
irradiation, almost no reaction was observed. In contrast, in
experiment 1, in which compound 1a was irradiated using 7 W
blue LED, it was almost completely converted to the target
product, osmanaphthalyne 2a. Therefore, the control
experiments 1 and 6 indicated that light was an essential
condition for the transformaion. Then, we hypothesized that this
kind of reaction is a light-induced free radical reaction. Therefore,
we added four different types of common free radical trapping
agents (TEMPO, 1, 1-diphenylethylene, hydroquinone, 2, 6-di-
tert-butyl-4-methylphenol) in experiments 2-5 to inhibit the
reaction. We were surprised to find that the characteristic peak
Figure 3. X-ray crystal structure of 4b shown with thermal ellipsoids at the
−
50% probability level. The anion BF4 and hydrogen atoms are omitted for
clarity.
The structure of α-osmaanthracyne (4a) and α-
osmaphenanthryne (4b) were also confirmed using X-ray
diffraction (Figures 3 and 4, Table S5, Tables S14 and S15).
The Os≡C bond lengths in 4a and 4b are 1.795 Å and 1.712 Å,
respectively, which are in agreement with the traditional Os≡C
bond length (Table 1). However, the three fused rings containing
osmium in complexes 4a and 4b have different coplanarity.
According to the related crystal data (Tables S14 and S15),
these compounds have different dihedral angles (18.06° for 4a
and 13.51° for 4b) between the plane of the naphthalene ring
and the plane (six-membered ring) where the Os≡C bond is
located. This may be because the steric hindrance at the α-
position of the naphthalene ring is greater than the steric
hindrance at the β-position, which leads to distortion when the
osmium hydrido alkenylcarbyne complexes 3a and 3b undergo
the visible light-induced intramolecular cyclization reaction, so
the resulting phenanthrene ring containing osmium atom of
compound 3a is more distorted. This is also consistent with the
(
=
14.34 ppm and -9.07 ppm) observed for the
osmanaphthalynes were still observed in 31P spectra, which
shows the four radical scavengers had no inhibitory effect on the
reaction. We guess that the mechanism of this visible light-
induced intramolecular cyclization reaction is similar to the
mechanism reported by the Xia group. In their studies, which
were induced by heat, an important osmium carbene
intermediate was formed via the migration of the hydride ligand
from osmium to the carbyne carbon atom. In the present study it
was the effect of visible light induction applied at room
temperature that induced this reaction.7b. It is worth mentioning
that our light-induced intramolecular cyclization is a green, mild
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and operationally convenient approach. In addition, the reaction
times are shorter and the yields are higher.
X-ray Crystallography
Single crystals of complexes 1b, 1c and 2b–2e suitable for X-ray
analysis were all obtained by slow diffusion of diethyl ether into a
dichloromethane solution of containing the corresponding compounds at
room temperature. Single crystals of complexes 3a and 3b suitable for X-
ray analysis were grown by slow diffusion of tetrahydrofuran into a
dichloromethane solution of containing the compounds of 3a and 3b. For
compound 4a, it was grown by slow diffusion of ethyl ether into a solution
of acetonitrile which containing the complex 4a. About compound 4b, it
was grown by slow diffusion of ethyl ether into
a solution of
dichloromethane with a little methanol. Intensity data were collected on a
Nonius Kappa CCD diffractometer with Mo Kα radiation (0.71073 Å) at
100 K or room temperature. The crystal structures were solved by direct
method with SHELXS-9714 and refined by SHELXL-2014. All non-H
atoms were refined anisotropically. The hydrogen atoms were placed in
ideal positions and refined as riding atoms. And partial distorted solvent
molecules have been omitted. Further crystal data and details of the data
collection are summarized in Tables S1–S5. Selected bond distances
and angles are given in Tables S6–S15. The crystallographic data for all
structures are available at the the Cambridge Crystallographic Data
Centre. CCDC 1841453, 1841467, 1841468, 1841455, 1841456,
1841457, 1841458, 1841459, 1846867, 1846868 for complexes 1b, 1c,
2b, 2c, 2d, 2e, 3a, 3b, 4a and 4b, respectively.
Figure 4. Comparison of 31P NMR spectrum (160 MHz, CDCl3) of six parallel
experiments at room temperature. 1) no radical scavenger, only with
irradiation; 2–5) both with irradiation and added with different radical
scavengers; 6) no radical scavenger, no irradiation. Red triangles indicate 31P
signal of the target products osmanaphthalynes, green triangles indicate 31P
signal of the open precursor (osmium hydrido alkenylcarbyne complex 1a).
In conclusion, we have synthesized
a
series of
Physical Measurements
osmanaphthalynes 2a–2b bearing different substituents (−H,
−Br, −I, −CH3 and −CF3), and the first examples of the one-
dimensional structure of α-osmaanthracyne 4a and two-
dimensional structure of α-osmaphenanthryne 4b using a room-
temperature intramolecular cyclization reactions, which is a
green, efficient and straightforward approach. To the best of our
knowledge, this paper is the first example of the application of a
visible light-induced method towards the synthesis of fused
heterocyclic complexes. The experimental results also proved
that this novel visible light-induced method is a widely applicable
and promising approach, and the oxygen and moisture in the air
have no effect on the reaction. Thus, such a method is in
complete agreement with the principles of green chemistry for
environmentally friendly chemical processes. We believe that
this green method will provide us with good strategies and ideas
for the design and synthesis of a wider variety and larger fused
heterocyclic complexes.
1H, 13C, 31P nuclear magnetic resonance (NMR) experiments (Figures
S21–S56, Supporting Information) were recorded on a Varian Mercury
Plus 400 spectrometer (400 MHz) or Varian MERCURY Plus 600 MHz
instrument. 1H and 13C NMR chemical shifts are given relative to Si(CH3)4,
and 31P NMR chemical shifts are relative to 85% H3PO4. Elemental
analyses (C, H, N) were performed with the Elementar Vario EL III
instrument. The high-resolution mass spectra (HRMS) experiments
(Figures S9–S20) were recorded using a Thermo Exactive plus mass
spectrometer. UV-Vis spectra were obtained on Shimadzu UV-3600
spectrophotometer.
General procedure for the synthesis of 1a–1e, 3a and 3b.
Experimental Section
General Materials.
Except for the visible light induced final step which was carried out
without nitrogen atmosphere protection, other manipulations were carried
out under a nitrogen atmosphere by using standard Schlenk techniques.
Solvents were distilled under nitrogen from sodium benzophenone (ether,
tetrahydrofuran) or calcium hydride (methanol), and degassed prior to
use. The starting materials of OsCl2(PPh3)3, 1a′–1e′, 3a′ and 3b′ were
prepared by procedures described in the literature.13 Other reagents
were used as received from commercial sources without further
purification.
Scheme 4. Synthetic routes of 1a–1e, 3a and 3b.
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V. Salazar, E. Oñate, K. Mereiter, J. Am. Chem. Soc. 2003, 125, 9898-
9899.
To a solution of OsCl2(PPh3)3 (1 eq) in appropriate amount of THF
solution, 1a′–1e′, 3a′ and 3b′ (1.2 eq) were added under nitrogen. The
reaction mixture was stirred for 4 h at room temperature to give yellow to
brown solution and then diethyl ether was added to the solution. The
yellowish to deep−yellow precipitates were collected by filtration, washed
with diethyl ether for three times and dried under vacuum to give crude
products. Because of the unstable characteristic, these compounds are
directly used in the next step of synthesis without further characterization.
Under nitrogen, a suspension of these crude products in moderate
amounts of methanol was treated with HBF4•Et2O (1.5 eq), and then the
mixture was heated under reflux for about 3 h. After the reaction mixture
was cooled to ambient temperature, the corresponding products were
obtained by filtration, washed by methanol and then dried in vacuo. Yield:
58–72%.
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without nitrogen protection, the mixture was stirred at room temperature
under 7 W blue LEDs (450−460 nm) at room temperature about 2–4 h.
The reaction time for each compound is 2a (3 h), 2b (3.5 h), 2c (3.5 h),
2d (4 h), 2e (2.5 h), 4a (4 h) and 4b (2 h), respectively. The solvent was
removed in vacuo. Addition of diethyl ether to the resulting residue led to
the green solids for 2a–2e, gray green solid for 4a and deep yellow solid
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Acknowledgements
The authors gratefully acknowledge financial support from
National Natural Science Foundation of China (21472059,
21772054).
Conflict of interest
The authors declare no conflict of interest.
Keywords: Osmanaphthalynes • Osmaanthracyne •
Osmaphenanthryne • Visible Light-induced • Fused metal
heterocyclic complexes
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Ming-Xing Zhang, Zhiqiang Xu, Tao Lu,
Jun Yin* and Sheng Hua Liu*
Page No. – Page No.
A Visible Light-Induced Strategy to
Construct Osmanaphthalynes,
Osmaanthracyne and
Osmaphenanthryne
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