Pd/Ni-Catalyzed Germa-Suzuki coupling via dual Ge-F bond activation

Article abstract of DOI:10.1039/d1cc01392k

Pd/Ni → Ge-F interactions supported by phosphine-chelation were found to trigger dual activation of Ge-F bonds under mild conditions. This makes fluoro germanes suitable partners for catalytic Ge-C cross-coupling and enables Germa-Suzuki reactions to be a

Full text of DOI:10.1039/d1cc01392k

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Pd/Ni-Catalyzed Germa-Suzuki coupling via dual
Ge–F bond activation†‡
Cite this: DOI: 10.1039/d1cc01392k
a
Hajime Kameo, *a Akihiro Mushiake,a Tomohito Isasa,a Hiroyuki Matsuzaka
b
Received 15th March 2021,
Accepted 20th April 2021
and Didier Bourissou
*
DOI: 10.1039/d1cc01392k
rsc.li/chemcomm
Pd/Ni - Ge–F interactions supported by phosphine-chelation were significantly advanced the use of Ge-based nucleophiles in
found to trigger dual activation of Ge–F bonds under mild condi- Ge–C(sp3) cross-coupling and described in 2019 a very elegant
tions. This makes fluoro germanes suitable partners for catalytic Germa-Negishi type reaction.7 We envisioned a radically different
Ge–C cross-coupling and enables Germa-Suzuki reactions to be approach, namely cross-coupling with a Ge-based electrophile.8
achieved for the first time.
Our recent discovery of facile Si–F bond activation thanks to
transition metal/Lewis acid cooperation opened the way to catalytic
Organo germanium compounds are powerful transfer reagents Sila–Negishi coupling from fluoro-silanes.9 Here we demonstrate
for catalytic cross-coupling reactions.1 They also find applica- that this concept can be extended to Germanium chemistry. The
tions in materials science.2 The formation of C–Ge bonds is combination of Pd or Ni with a Lewis acid enables dual activation
thus of importance and the advent of new synthetic methodologies of Ge–F bonds.10 Accordingly, fluoro germanes were found to
is highly desirable to widen the scope of usable substrates and undergo Ge–C cross-couplings with organo boron reagents, pro-
accessible products.
viding the first examples of Germa-Suzuki reactions.
Hydrogermylation involving transition metal or radical-
Fluoro germanes have been shown in previous studies to
mediated pathways is efficient and useful, but intrinsically engage in M - Ge–F interactions (M = Cu, Ag, Au) when
limited to the synthesis of alkyl- and alkenyl-substituted chelated by phosphines, and to be stronger s-acceptor ligands
germanes.3–5 The most general way to forge Ge–C bonds is than fluoro silanes.11 We thus envisioned to take advantage of
probably the ionic coupling of organometallic compounds with P-chelation to trigger Ge–F activation and cross-coupling. Given
germanium halides or alkoxides (reactions between Ge-based
nucleophiles and organic electrophiles are also known but less
common).6 Transition metal catalysis is extremely powerful and
broadly used for C–C and C–X bond formation. It has certainly
great potential for Ge–C cross-coupling as well, although the
field is still in its infancy with only very few recent reports
(Fig. 1). Xiao and co-workers reported in 2018 Pd-catalyzed
couplings of a hydrogermatrane with aryl halides and pseudo-
halides.1d The approach was then extended by Schoenebeck
et al. to the coupling of Et3GeH with aryl thiathrenium salts
using Pd(I) dimers as catalysts.1k In addition, Oestreich et al.
a Department of Chemistry, Graduate School of Science,
Osaka Prefecture University, Osaka 599-8531, Japan.
E-mail: h.kameo@c.s.osakafu-u.ac.jp
b
´ ´
´
´
Laboratoire Heterochimie Fondamentale et Appliquee, Universite Paul Sabatier/
CNRS UMR 5069, 118 Route de Narbonne, 31062 Toulouse Cedex 09, France.
E-mail: dbouriss@chimie.ups-tlse.fr
´
† Dedicated to Dr Jean Escudie.
‡ Electronic supplementary information (ESI) available: Experimental procedures
and analytical data (PDF). CCDC 2049747–2049750. For ESI and crystallographic
data in CIF or other electronic format see DOI: 10.1039/d1cc01392k
Fig. 1 Transition metal-catalyzed Ge–C cross-couplings.
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Table 1 Germa-Suzuki cross-coupling reactions of the fluoro germanes
1Ge and 3
Table 2 Scope of borate reagents for the Germa-Suzuki coupling of
fluoro germane 5ab
Entry
Substrate
Catalyst
Ar source/L.A.
Yielda (%)
b
1
2
3
4
1Ge
1Ge
1Ge
1Ge
1Si
3
Pd2(dba)3
Ni(COD)2
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Ni(COD)2
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Ni(COD)2
Ni(COD)2
7Ge
BPh3b
99
99
0
0
0
79
47
0
BPh3
PhBpinc
b
B(C6F5)3
b
5
BPh3b
6d
7d
8d
9d
10
11
12
13
14
BPh3b
BPh3
3
3
3
PhBpinc
a
Spectroscopic yields, as determined by 31P NMR spectroscopy
b
B(C6F5)3
0
b
(isolated yields are given in parentheses). 120 1C.
1Ge
1Ge
1Ge
3
K(F3BPh)/BF3ÁOEt2
K(F3BPh)/BF3ÁOEt2
K(F3BPh)/none
49 (96)e
8 (99)ef
0 (0)e
86
b
The substrate scope was then investigated employing the
following optimal conditions: Ni(COD)2, K(F3BR) and BF3 in
2-MTHF (Table 2). Phenylation of the fluoro germane {(o-Ph2P)
C6H4}GeMe2F (5) featuring methyl substituents at Ge worked
nicely. The reaction proceeded well with a variety of trifluoro
(aryl)borates featuring electron-donating (OMe, NMe2) as
well electron-withdrawing (CN, CF3, F, Cl) groups. Ge–C(sp3)
coupling worked with K(F3BBn) but not with n-alkyl substrates
prone to b-H elimination such as K[EtBF3] and K[n-BuBF3]
(ESI‡).
BPh3b
3
8cGe
BPh3
89
a
b
c
d
Determined by 31P NMR. 1.5 eq. 5 eq. 10 mol% catalyst, Mesity-
e
f
lene, 160 1C, 20 h. 2-MTHF. Isolated yield: 68%.
the availability and efficiency of boron reagents as nucleophiles,
we sought to develop a hitherto unknown Germa-Suzuki reaction.
The fluoro germane {(o-Ph2P)C6H4}GePh2F 1Ge was used as sub-
strate and several aryl boron derivatives were tested. Gratifyingly,
quantitative Ge–Ph coupling was observed using BPh3 with either
Pd2(dba)3 or Ni(COD)2 (Table 1, entries 1 and 2). The nature of the
borane is critical: no reaction occurred when the less Lewis acidic
borane PhBpin or the very Lewis acidic borane B(C6F5)3 were useÀd
(entries 3 and 4). The formation of F2BPh, BF3, and BF4
by-products from BPh3 (as apparent from 19F{1H} NMR spectro-
scopy, Fig. S1, ESI‡) suggests that the borane acts both as Ph
source (arylating reagent) and a F acceptor (Lewis acid) in this
transformation. Of note, the corresponding fluoro silane {(o-Ph2P)
C6H4}SiPh2F (1Si) remains inert under similar conditions (entry 5),
indicating that only the Ge–F bond can be activated and cross-
coupled this way, probably due to stronger M - Ge–F interaction.
Phenylation of the diphosphine fluoro germane {(o-Ph2P)C6H4}2
GePhF (3)10 was also possible with both Pd and Ni catalysts using
BPh3 (entries 6 and 7). Again, no cross-coupling was observed
using PhBpin or B(C6F5)3 (entries 8 and 9). Varying the aryl source
and Lewis acid with 1Ge as substrate, we then realized that the
reaction can be most conveniently achieved using the trifluoro-
borate salt K(F3BPh) along with BF3. With this combination,
modest results were obtained in THF (probably due to inhibition
of the Lewis acid-assisted Ge–F activation). However, shifting to
2-methyl tetrahydrofuran (2-MTHF) as solvent drastically
improved the catalytic activity and the desired Ge–Ph coupling
product 2 was obtained in excellent yields (entries 10 and 11).
Note that K[F3BPh] alone is unproductive, the concomitant use of
BF3 is essential for the catalysis to proceed (entry 12). Phosphine
chelation also plays an important role, no reaction being observed
under the same conditions from FGePh3.
Competitive experiments12 were then carried out with a 1 : 1
mixture of 5 and 5Cl in order to compare the reactivity of fluoro
and chloro germanes towards Ge–C coupling (Fig. 2). When
ZnPh2 was used as arylating reagent, only the chloro germane
reacted to give 6-Ph. An opposite chemo-selectivity was
achieved with Ni(COD)2, K(F3BR) and BF3. Only the fluoro
germane 5 was found to undergo cross-coupling under these
conditions, 5Cl remained unchanged.
By analogy with the related Sila–Negishi coupling,9 we
propose the catalytic cycle shown in Fig. 3 to account for the
Germa-Suzuki coupling. To support the feasibility and rele-
vance of this pathway, the formation, structure and reactivity of
Pd complexes deriving from the diphosphine fluoro germane 3
were investigated. Complex 7Ge was first synthesized by ligand
exchange (step i). In contrast with the related diphosphine
fluoro silane complex,9 7Ge proved unstable in the absence of
Fig. 2 Competitive phenylations of Ge–Cl and Ge–F bonds.
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BPh3 markedly contrasts with the inertness of the Si–F bond of
7Si under similar conditions. The fluoro silane complex
remains unchanged when treated with BPh3 even upon heating
at 160 1C (see below for a tentative explanation based on DFT
calculations). Interestingly, the Ge–F bond activation is rever-
sible. Indeed, the addition of tetrabutylammonium fluoride
(TBAF) to 8Ge-BPh4 at room temperature immediately and
quantitatively regenerates the fluoro germane complex 7Ge
.
The interconversion of Z-type and X-type ligands has recently
attracted much interest and clear-cut examples have been
authenticated with B,18 Si,9 Sb19 and Sn.20 To our knowledge,
the back and forth between 7Ge and 8Ge represents a first case
with Z-germane and X-germyl moieties.
To gain further insight into the Ge–F bond activation from
the fluoro germane 7Ge to the germyl 8Ge species, DFT calcula-
tions were performed with BPh3 as Lewis acid (Fig. 4). For
comparison, similar studies were carried out on Si–F bond
activation. The interaction of 7Ge with BPh3 is slightly exergonic
(DG = À0.4 kcal molÀ1). It induces further elongation of the
Ge–F bond (from 1.866 to 1.894 Å) while the Pd–Ge bond
slightly shortens (from 2.777 to 2.741 Å). The subsequent bond
cleavage is exergonic (DG = À6.3 kcal molÀ1) and takes place
Fig. 3 Catalytic cycle proposed to account for the Germa-Suzuki
coupling. Molecular structures of the isolated catalytic intermediates 7Ge
(a), 8Ge (b) and 9-C6F5 (c) complexes (the Ph substituents at phosphorus
and germanium are simplified, the hydrogen atoms and counter-anion for
8Ge are omitted for clarity).
with very small Gibbs activation energies (DG‡ = 2.4 kcal molÀ1
)
to give the cationic germyl complex 8Ge-FBPh3. Activation of the
Si–F bond of 7Si with BPh3 proceeds similarly with a slightly
excess PPh3. Notwithstanding, crystals of 7Ge suitable for X-ray higher but still low activation barrier (DG‡ = 5.1 kcal molÀ1). It
diffraction analysis could be obtained (Fig. 3(a)). The Pd center is endergonic (DG = 3.7 kcal molÀ1), why may explain why no
is in tetrahedral environment, with the fluoro germane moiety catalytic conversion was observed for this substrate (entry 5 in
coordinated via Ge (PdÁ Á ÁGe 2.7518(5) Å) and Cipso (PdÁ Á ÁC Table 1). In line with this energy landscape, spontaneous
2.638(3) Å) in addition to the three P atoms. The germane fluoride transfer was observed upon mixing the fluoro germane
moiety behaves as a Z-type ligand in complex 7Ge 11,13,14
Ge–Pd distance is only slightly longer than the sum of covalent germyl 8Ge-BPh4 and fluoro silane 7Si species (ESI‡).
radii (2.53 Å),15 and despite the larger radius of Ge compared to
To promote B-to-Pd transmetalation (step iii), 8Ge-BPh3F
.
The 7Ge and silyl 8Si-BPh4 complexes to give the corresponding
Si (1.20 vs. 1.11 Å),15 it is significantly shorter than the PdÁ Á ÁSi was then thermolyzed. The corresponding phenyl complex
distance in the Si analogue of 7Ge (2.9770(8) Å in [{(o-Ph2P) [{(o-Ph2P)C6H4}2PhGe]{Pd(Ph)} (9-Ph) was quantitatively obtained
C6H4}2SiPhF][Pd(PPh3)] (7Si)).9 Additional signs for Pd - Ge–F after 1 h at 160 1C. Complex 9-Ph proved too unstable to be
interaction in complex 7Ge are the elongation of the Ge–F bond isolated in pure form, but the analogous pentafluorophenyl
[1.8246(19) Å vs. 1.762(2) Å in {(o-Ph2P)C6H4}3GeF16] and the species [{(o-Ph2P)C6H4}2PhGe]{Pd(C6F5)} 9-C6F5 could be fully
trigonal pyramidal geometry around Ge [the sum of C–Ge–C characterized (X-ray structure is shown in Fig. 3(c)) (ESI‡). It is
angles = 358.81(22)1, PdÁ Á ÁGe–F bond angle = 157.94(6)1]. Con- formed when reacting the fluoro germane complex 7Ge with
sistently, NBO analysis (DFT) shows the presence of a substantial B(C6F5)3 followed by thermolysis. Transmetalation required pro-
donor–acceptor d(Pd) - s*(Ge–F) interaction (15.8 kcal molÀ1) at longed heating (83% conversion after 20 h at 160 1C) and was less
the second-order perturbation level.
Activation of the Ge–F bond at Pd was then studied (step ii).
Upon treatment with boranes such as BF3, BPh3 and B(C6F5),
complex 7Ge readily afforded the cationic germyl complex
[{(o-Ph2P)C6H4}2PhGe{Pd(PPh3)}][FBR3] (8Ge-FBR3) (R = F, Ph,
C6F5)).17 The molecular structure of 8Ge was confirmed by X-ray
diffraction analysis after counter-anion exchange (complex
8Ge-BPh4, Fig. 3(b)). As expected, the Pd–Ge distance
[2.4051(3) Å] is much shorter than in 7Ge and only marginally
exceeds the sum of covalent radii. With a less Lewis acidic
borane such as PhBpin, the germane 7Ge remains intact, in line
with the absence of catalytic activity observed when using
PhBpin as coupling partner (entries 3 and 8, Table 1). Note
that the facile Ge–F bond cleavage from 7Ge in the presence of assisted by BPh3. Free Gibbs energy changes (kcal molÀ1) in THF.
Fig. 4 Reaction profiles computed for the Si/Ge–F bond cleavage at Pd
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clean (44% yield) in this case. The last step of the catalytic cycle, i.e.
Ge–C coupling via reductive elimination (step iv), could also be
achieved from 9-Ph. Thermolysis in the presence of 3 (1 h, 160 1C)
cleanly and quantitatively afforded the Ge-arylation product 4 along
with the fluoro germane complex 7Ge. Note that heating 9-C6F5 led
to intractable mixtures, with no detectable Ge–C6F5 product, in line
with the much lower reactivity of C6F5 towards reductive elimina-
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Lewis acid/arylating reagent (entries 4 and 9 in Table 1).
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BPh3 (entries 13 and 14 in Table 1). Catalytic activities similar to
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(in about 8 : 1 ratio) when monitoring the catalysis. This is con-
sistent with the fact that transmetalation and reductive elimination
require more forcing conditions than Ge–F bond activation.
In conclusion, Pd/Ni-catalyzed Germa-Suzuki coupling reac-
tions have been carried out for the first time. Fluoro germanes
were used as electrophilic coupling partners. The key Ge–F
bond cleavage was achieved thanks to phosphine-chelated
Pd/Ni - Ge–F interactions. Future work will aim to extend
further the application of Z-type coordination to the activation
and functionalization of strong s-bonds.
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This work was supported by Grant-in-Aid for Scientific
Research (C) (No. 18K05151 and 18K05152) of the Ministry of
Education, Culture, Sports, Science and Technology (MEXT),
Japan. H. K. acknowledges the financial support from the
Tokyo Ohka Foundation for the Promotion of Science and
Technology. The Centre National de la Recherche Scientifique
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