Titanium Carbene Complexes Stabilized by Alkali Metal Amides

Article abstract of DOI:10.1002/anie.201812579

Facile α-H elimination from tetrakis(trimethylsilylmethyl)titanium precursors to give adducts of (alkylidene)bis(alkyl)titanium complexes is induced by light alkali metal amides of the NNNN-type macrocyclic anionic ligand Me₃TACD [(Me₃

Full text of DOI:10.1002/anie.201812579

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Accepted Article
Title: Titanium Carbene Complexes Stabilized by Alkali Metal Amides
Authors: Jun Okuda, Hassan Osseili, Khai-Nghi Truong, Thomas P.
Spaniol, Laurent Maron, and Ulli Englert
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201812579
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10.1002/anie.201812579
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Titanium Carbene Complexes Stabilized by Alkali Metal Amides
Hassan Osseili,a Khai-Nghi Truong,a Thomas P. Spaniol,a Laurent Maron,*,b Ulli Englert,*,a and Jun
Okuda*,a
trimethylsilylmethylidene carbon.[6i] AB spin patterns for the
diastereotopic protons of the CH2SiMe2Ph methylene groups of
1b, 2b and 3b suggest coordination of the [M(Me3TACD)] unit.
Abstract: Facile -H elimination in tetrakis(trimethylsilylmethyl)-
titanium precursors to give adducts of (alkylidene)bis(alkyl)-
titanium complexes is induced by light alkali metal amides of the
NNNN-type macrocyclic anionic ligand Me3TACD [(Me3TACD)H:
1,4,7-trimethyl-1,4,7,10-tetraazacyclo-dodecane]. In the crystal,
the alkali metal interacts with the carbene carbon or with the CH2
group of trimethylsilymethyl ligand. Nucleophilic character of the
carbene carbon was shown by the reaction with benzophenone
and terminal acetylene.
Such
a
feature
was
also
as
observed
well as
for
for
[(PNP)Ti(=CHtBu)(CH2SiMe3)]
[(PNP)Ti(=CHtBu)(CH2Ph)].[6s,8]
N
N
N
RMe2Si
RMe2Si
N
M
Ti
C
Transition metal alkylidene complexes are used in olefin
metathesis[1], Wittig-type reactions,[2] and in the transformation of
small molecules.[3] Schrock-type metal alkylidenes are commonly
formed by α-hydrogen abstraction,[4] promoted by steric repulsion
of bulky (alkyl) ligands.[5] A number of group 4 metal alkylidene
complexes were reported in the last decades, although a simple
H
RMe2Si
1a
1b
(61%)
M = Li, n = 2, R = Me,
(77%); R = Ph,
23 °C, 5 min
2b
M = Na, n = 3, R = Ph,
(62%)
n-pentane
M = K, R = Ph, 3b (89%)
1/n [(Me3TACD)M]n
[Ti(CH2SiMe2R)4]
- CH3SiMe2R
N
N
N
trimethylsilylmethylidene
bis(trimethylsilylmethyl)
complex
Me3Si
N
remained unknown [6]
.
Here, we present a remarkably facile
M
Ti
H
C
Me3Si
access to titanium trimethylsilylmethylidene complexes which are
stabilized by an alkali metal that carries an NNNN-type
H
Me3Si
monoanionic polyamine ligand.
M = Na, n = 3, 2a (71%)
3a
M = K,
(89%)
The easily accessible alkali metal amides [(Me3TACD)M] (M = Li,
Na, K, (Me3TACD)H = 1,4,7-trimethyl-1,4,7,10-tetraazacyclo-
dodecane) contain an amido group that can serve as a π-donor or
as a bridging ligand.[7] When this compound was added to a
solution of [Ti(CH2SiMe2R)4] (R = Me, Ph) in n-pentane at ambient
temperature, intramolecular α-hydrogen abstraction instantan-
eously occurred. The titanium alkylidene complexes
Scheme 1. Formation of the titanium alkylidene complexes 1-3.
[{(Me3TACD)M}Ti(=CHSiMe2R)(CH2SiMe2R)2]
with
the
trimethylsilylmethylidene ligand [R = Me, M = Li (1a), Na (2a), K
(3a)] and with the phenyldimethylsilylmethylidene ligand [R = Ph,
M = Li (1b), Na (2b), K (3b)] were obtained under elimination of
SiMe3R (R = Me, Ph) as the only by-product (Scheme 1).
The titanium carbenes 1-3 were isolated as deep red crystals. 1H
NMR spectra in C6D6 show a characteristic signal for the α-proton
of the alkylidene moiety at low field (δ 8-9 ppm). The
diastereotopic CH2SiMe3 methylene groups in 1a appear as a
singlet at  1.13 (1a) ppm. This may indicate fast dissociation of
the [(Me3TACD)M] unit, fast α-hydrogen migration on the NMR
time scale down to −80 °C, or isochrony (coincidental overlap). In
the 13C NMR spectra, the carbene signal of the Ti=CHSiMe3 unit
Figure 1. Molecular structure of 1a. Displacement parameters are displayed at
50% probability. Only the hydrogen atoms of the carbene unit Ti=CH is shown.
Selected interatomic distances (Å) and angles (°): Ti1−C1: 1.929(4), Ti1−C5:
2.130(4), Ti1−C9: 2.105(4), Ti1−N1: 1.996(3), Li1⋯C1: 2.299(7), Li1−N1:
2.306(6); ∠(Ti1−C1⋯Li1): 83.92(19), ∠(Ti1−C1−H1): 104(3), ∠(Ti1−C1−Si1):
139.8(2).
(δ 240-310 ppm) falls within the expected range for
a
Both lithium complexes 1a and 1b have been characterized by
single crystal X-ray diffraction (Fig. 1 and Fig. S24) and show a
closely related molecular framework. The titanium center is
tetrahedrally coordinated, the lithium ion interacts with the four
nitrogen atoms of the Me3TACD ligand and the carbene carbon
in distorted square-pyramidal geometry. Compared to the
Ti−CAlkyl distances [2.105(4)−2.130(4) Å], the short distances
between titanium and the carbene carbon Ti1−C1 of 1.929(4) Å
(1a) and 1.923(4) Å (1b) indicate double bond character. The
distance between the lithium center and the carbene carbon
Li1−C1 of 2.299(7) Å (1a) and 2.368(8) Å (1b) suggests a strong
interaction as in the structurally related compound
[(Me3SiCH2)(ArN=)Ta(µ-CHSiMe3)(µ-η1:η3-iPr2-TACN)Li].[4b, 4c, 9]
[*]
H. Osseili, K.-N. Truong, Dr. T. P. Spaniol, Prof. Dr. U. Englert,
Prof. Dr. J. Okuda
Institute of Inorganic Chemistry
RWTH Aachen University
Landoltweg 1, 52056 Aachen, Germany
E-mail: jun.okuda@ac.rwth-aachen.de
Prof. Dr. L. Maron
CNRS, INSA, UPS, UMR 5215, LPCNO
Université de Toulouse
135 avenue de Rangueil, 31077 Toulouse, France
Supporting information for this article, including experimental
procedures, crystallographic and spectroscopic details, and
computational analyses, is available on the WWW under
http://dx.doi.org/10.1002/XXX
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10.1002/anie.201812579
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COMMUNICATION
titanium-carbon double bond is re-protonated. This reaction can
only occur if the basicity of the carbene unit in the intermediate is
sufficiently strong. DFT calculations confirm a carbene as a
potential intermediate (Fig. S59), that reacts further to the more
stable CH-bond activation product 4 (Fig. S60). The titanium
carbene complexes 1-3 also decomposed after 20 min to give
products of intramolecular CH-bond activation along with
unidentified byproducts (see SI).
This is associated with distortions [∠(Ti1−C1⋯Li1) of 83.92(19)°
(1a) and 83.2(2)° (1b), ∠(Ti1−C1⋯H1) of 104(3)° (1a) and 108(3)°
(1b), ∠(Ti1−C1−Si1) of 139.8(2)° (1a) and 137.8(2)° (1b)]. The
phenyl ring of the CHSiMe2Ph unit in 1b is directed towards the
lithium center. This additional interaction is not very pronounced
[Ti1−C4: 3.844(6) Å], but explains the slightly smaller Li1-C1
distance in 1b than in 1a. Geometry optimizations were carried
out on complexes 1a and 1b at the DFT level (B3PW91). In both
cases, the HOMO displays a Ti-carbene π-interaction (Fig. 2) that
is stabilized by hyperconjugation with either the Si-C bond (1a) or
the phenyl ring (1b) and to a lesser extent by the interaction with
the lithium center (Fig. 2).
Figure 3. Molecular structure of 4. Displacement parameters are shown at 50%
probability. Atom sites with minor occupancies are omitted for clarity. Selected
interatomic distances (Å): Ti1−C1A: 2.176(7), Ti1−C12A: 2.178(9), Ti1−C17A:
2.328(12), Ti1−C22: 2.114(5), Ti1−N1A: 1.989(5), Li1⋯C17A: 2.44(2).
The sodium congener 2b shows a similar molecular structure as
the lithium compound 1b in the solid state (Fig. 4), with the
Me3TACD ligand κ4-coordinated to the sodium center and the
titanium in tetrahedral geometry.
Figure 2. Representation of the HOMO in the lithium compound 1a.
The reaction of the lithium amide [(Me3TACD)Li]2 with the
neopentyl compound [Ti(CH2CMe3)4] did not give alkylidene
complex A as would be expected from the analogous reaction
with [Ti(CH2SiMe3)4], but the alkyl derivative 4. This compound
could be isolated by crystallization from n-pentane at −30 °C after
24 h.
N
N
H
H
N
N
N
N
H
N
N
Li
H
1/2 [(Me3TACD)Li]2
- H3CCMe3
[Ti(CH2CMe3)4]
Li
H
C
Ti
Ti
H
C
23 °C, 15 min
n-pentane
4
A
Scheme 2. Formation of CH-bond activated complex 4.
Figure 4. Molecular structure of 2b. Displacement parameters are displayed at
50% probability. Only the hydrogen atom of the T=CH is shown. Selected
interatomic distances (Å) and angles (°): Ti1−C19: 2.135(3), Ti1−C10: 2.118(3),
Ti1−C1: 1.921(3), Ti1−N1: 1.963(2), Na1⋯C1: 2.624(3), Na1−N1: 2.655(2),
Na1⋯C4: 3.385(4), Na1⋯C5: 3.227(4), Na1⋯C9: 4.212(4); ∠(Ti1−C1⋯Na1):
87.55(10); ∠(Ti1−C1−H1): 106.6(18), ∠(Ti1−C1−Si1): 142.41(14).
Crystal structure determination by X-ray diffraction revealed the
molecular structure (Fig. 3). In spite of significant disorder, the
refinement could be carried out with split positions and confirms
the connectivity. The five-coordinate lithium center is found in
distorted square pyramidal geometry coordinated by the four
nitrogen atoms of the macrocyclic ligand and by a carbon atom of
an alkyl group [Li1-C17A: 2.481(13) Å; Li1-C17B: 2.435(18) Å].
Striking feature is the Ti1-C1A distance of 2.176(7) Å indicating
bonding between titanium and a carbon atom of the deprotonated
carbon atom within the ligand Me3TACD. Similar CH-bond
activation was reported for complex [(L)Ti(benzyl)]2 (L = 3,3-
dimethyl-1,5-diaza-8-oxacyclodecane).[10] The coordination of the
macrocyclic ligand after CH-activation leads to a C1-symmetric
molecular structure which is also suggested by the signal pattern
in the 1H NMR spectrum. The 1H and the 13C NMR spectra do not
show a signal that would correspond to a carbene unit. We explain
the formation of 4 by intermediate formation of a carbene complex,
that activates a CH-bond of the macrocyclic ligand whereby the
As in 1b, the phenyl substituent in 2b is directed towards the
alkaline metal ion, caused by the π-interaction to the slightly tilted
phenyl ring with short Na1−CPhenyl distances [Na1⋯C4: 3.385(4)
Å, Na1⋯C5: 3.227(4) Å] rather than due to a strong interaction
between sodium and the carbene unit [Na1⋯C1: 2.624(3) Å] (vide
infra). Non-covalent M+ꞏꞏꞏCPhenyl interactions for group 1 metals
are common, especially for the heavier congeners resulting in
coordinative saturation.[11]
In the closely related structures of the sodium and the potassium
compounds 2a and 3a, the trimethylsilylmethylidene ligand
[Ti1−C1: 1.879(3) Å (2a), 1.867(9) Å (3a)] is pointing away from
the alkali metal. The latter shows a weak interaction to one of the
CH2SiMe3 methylene groups [Na1⋯C5: 2.893(4) Å (2a); K1⋯C5:
3.163(8) Å (3a)] (Fig. 5). Neither the sodium nor the potassium
center seems Lewis acidic enough to interact with the carbene
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10.1002/anie.201812579
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moiety. Fig. 5 shows the free open site at the alkali metal which
easily coordinates thf as a donor ligand. Whereas the potassium
compound 3a is insoluble in pentane, a trace of thf transforms 3a
into the soluble derivative 3a*thf. Apart from the additional donor
ligand, the main structural framework within 3a and 3a*thf is
closely comparable (see Fig. 4 and Fig. S17).
spectroscopy in comparison with literature values after work-
up.[13] The formation of this silane is expected if a Wittig−type
reaction occurs and confirms a Schrock−type alkylidene ligand in
1a. The reactivity resembles that of Tebbe’s reagent or that of the
comparable complex [(Me3SiCH2)(ArN=)Ta(µ-CHSiMe3)(µ-η1:η3-
iPr2-tacn)Li] reported by Arnold and coworkers.[4b, 4c, 6f, 6j,12] Notably,
the complex 1a did not react with olefins such as styrene or 1-
hexene even at 60 °C.
When 1a was treated with one equivalent of phenyl- or
trimethylsilylacetylene in n-pentane at ambient temperature, the
solution turned orange. Cooling to −30 °C gave the acetylide
complexes 5a or 5b as orange crystals (Scheme 3).
N
N
N
N
N
N
Me3Si
Me3Si
N
N
R
X
X
H
Me3Si
Li
Li
Ti
Ti
Me3Si
C
n-pentane
10 min, 25 °C
H
Me3Si
R
Me3Si
Figure 5. Molecular structures of 2a and 3a. Displacement parameters are
shown at 50% probability. Hydrogen atoms except Ti=CH and TiCH2SiMe3 are
omitted for clarity. Selected interatomic distances (Å) and angles (°): for 2a =
Ti1−C1: 1.879(3), Ti1−C5: 2.150(3), Ti1−C9: 2.160(3), Ti1−N1: 1.964(3),
Na1⋯C5: 2.893(4), Na1⋯H5A: 2.408(4), Na1⋯H5B: 2.802(4), Na1−N1:
2.613(3); ∠(Ti1−C5⋯Li1): 80.1(1), ∠(Ti1−C1−H1): 87.0(2), ∠(Ti1−C1−Si1):
151.9(2). For 3a = Ti1−C9: 2.164(8), Ti1−C5: 2.128(9), Ti1−C1: 1.867(9),
Ti1−N1: 1.958(6), K1⋯C5: 3.163(8), K1⋯H5A: 2.832(2), K1⋯H5B: 2.944(2),
K1−N1: 2.928(6); ∠(Ti1−C5⋯K1): 79.2(3), ∠(Ti1−C1−H1): 96.9(6),
∠(Ti1−C1−Si1): 145.3(5).
5a
(72%)
R = SiMe3, X = H,
(66%)
5b
R = Ph, X = H,
R = Ph, X = D,
5-d
1 (63%)
Scheme 3. Reaction of 1a with phenyl- and trimethylsilylacetylene.
The 1H NMR spectra show the CH2SiMe3 fragments with singlets
for the methylene groups [δ 2.20 ppm (5a) and 2.10 ppm (5b)],
and for the methyl groups [δ 0.55 ppm (5a) and 0.52 ppm (5b)].
The signal of the α-hydrogen atom of the carbene CH unit
disappeared. In a deuterium labelling study, the reaction of 1a
with phenylacetylene-d1 provided the deuterated complex 5b-d1
which was also characterized by 2H NMR spectroscopy. The
deuterium signal appeared as a singlet at δ 2.21 ppm.
DFT calculations were carried out to determine the role of the
alkali metal center. The coordination geometries in 2b, 2a and 3a
were reproduced. As in 1a and 1b, the HOMO shows strong 
interactions between titanium and the carbene ligand as well as
hyperconjugation to the SiR3 units (Fig. 2 and Fig. 6). 2a and 3a
(Fig. 6) were found as conformers where the carbene unit does
not show an interaction with the alkali metal, unlike for 1a (Fig. 2).
The crystal structures of 5a and 5b show a titanium center in
distorted trigonal bipyramidal geometry (Fig. 7 and Fig. S50).
Figure 7. Molecular structure of 5a. Displacement parameters are shown at
50% probability. Selected interatomic distances (Å): Ti1−C1: 2.258(2), Ti1−C6:
2.171(2), Ti1−C10: 2.135(2), Ti1−C14: 1.149(2), Ti1−N1: 1.939(2), Li1⋯C1:
2.218(4), Li1⋯C2: 2.568(5), Li1−N1: 2.394(4), C1−C2: 1.226(3).
All titanium-carbon distances are in the range of Ti–C single
bonds [5a: Ti1−C1: 2.258(2) Å, Ti1−C10: 2.171(2) Å, Ti1−C10:
2.135(2) Å, Ti1−C14: 2.149(2) Å; 5b: Ti1−C1: 2.225(3) Å, Ti1−C9:
2.166(3) Å, Ti1−C13: 1.162(3) Å; Ti1−C17: 2.125(3) Å] (Fig. 7).
The C1−C2 distance of 2.226(3) Å (5a) and 1.221(4) Å (5b)
corresponds to the expected triple bond and in both complexes
the alkyne moiety exhibits an intramolecular interaction with the
lithium center [5a: Li1⋯C1: 2.218(4) Å, Li1⋯C2: 2.568(5) Å; 5b:
Li1⋯C1: 2.201(5) Å, Li1⋯C2: 2.569(5) Å]. Similar interactions
between alkali metals and triple bonds in titanium complexes have
been reported.[13] The lithium amide Li{N(SiHMe2)2} without a
Me3TACD ligand did not react with [Ti(CH2SiMe3)4].
In conclusion, we have reported the facile formation of a series of
titanium alkylidene complexes with the trimethylsilylmethylidene
(1a, 2a, 3a) and phenyldimethylsilylmethylidene (1b, 2b, 3b)
ligand. The neopentyl derivative [Ti(CH2CMe3)4] reacted with
[M(Me3TACD)] to give the product of the CH-bond activation at
the NNNN-type macrocyclic ligand. Computational studies agree
with the alkylidene carbon in 1a to be stabilized by interaction with
the Lewis acidic lithium center. Wittig-type reaction of 1a with
benzophenone as well as protonation by terminal acetylene to
Figure 6. Representation of the HOMO in the sodium compound 2a.
An isomer of lithium compound 1a with a larger distance between
the carbene and the alkali metal (like in 2a) would also be stable,
but 3.3 kcal.mol-1 higher in energy. This situation is even more
pronounced in the SiMe2Ph substituted sodium complex 2b,
because no other stable conformer with the carbene ligand
pointing away from the alkali metal was located on the potential
energy surface (PES). The experimentally observed complex 2a
is actually 3.0 kcal.mol-1 less stable than the calculated conformer
where the carbene ligand interacts closer with the alkali metal (like
in 1a and 2b). The geometry in 2a with the carbene ligand poining
away from the alkali metal is therefore due to steric effects that
block the structure in a secondary minimum.
Treatment of complex 1a with one equivalent of benzophenone in
C6D6 led to a color change from deep red to light yellow within 15
min. The 1H NMR spectrum confirms the formation of
(2,2-diphenylethenyl)trimethylsilane as characterized by 1H NMR
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COMMUNICATION
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Acknowledgments
[7]
We thank the Deutsche Forschungsgemeinschaft through the
International Research Training Group “Selectivity in Chemo-
and Biocatalysis” (IRTG 1628) for financial support.
[8]
Keywords: titanium • carbene • alkylidene • alkali metal • Wittig
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