The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl

Article abstract of DOI:10.1002/chem.201805604

The first donor–acceptor complex of a silaaldehyde, with the general formula (NHC)(Ar)Si(H)OGaCl₃ (NHC=N-heterocyclic carbene), was synthesized using the reaction of silyliumylidene–NHC complex [(NHC)₂(Ar)Si]Cl with water in the presence of GaCl₃. Conversion of this complex to the corresponding silacarboxylate dimer [(NHC)(Ar)SiO₂GaCl₂]₂, free silaacetal ArSi(H)(OR)₂, silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl₃, and phosphasilene–NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true potential as a synthon in silacarbonyl chemistry.

Full text of DOI:10.1002/chem.201805604

A Journal of
Accepted Article
Title: The Quest for Stable Silaaldehydes: Synthesis and Reactivity of
a Masked Silacarbonyl
Authors: Shigeyoshi Inoue, Debotra Sarkar, Vitaly Nesterov, Tibor
Szilvasi, and Philipp Altmann
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
to this Accepted Article as a result of editing. Readers should obtain
the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Chem. Eur. J. 10.1002/chem.201805604
Link to VoR: http://dx.doi.org/10.1002/chem.201805604
Supported by

10.1002/chem.201805604
Chemistry - A European Journal
COMMUNICATION
The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a
Masked Silacarbonyl
Debotra Sarkar,[a] Vitaly Nesterov,[a] Tibor Szilvási,[b] Philipp J. Altmann,[a] and Shigeyoshi Inoue*[a]
Abstract: First donor-acceptor complex of a silaaldehyde, compound
with general formula (NHC)(Ar)Si(H)OGaCl3, was synthesized using
the reaction of silyliumylidene–NHC complex [(NHC)2(Ar)Si]Cl with
water in the presence of GaCl3. Conversion of this complex to the
corresponding silacarboxylate dimer [(NHC)(Ar)SiO2GaCl2]2, free
silaacetal ArSi(H)(OR)2, silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl3, and
phosphasilene–NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true
potential as a synthon in silacarbonyl chemistry.
Carbonyl group is important and ubiquitous functionality in the
field of organic chemistry, life sciences and beyond.[1] While
aldehydes, ketones, and carboxylic acid derivatives are generally
well-known stable organic compounds, the synthesis and
isolation of their stable heavier group 14 analogues is
challenging.[2] The instability and high tendency to oligomerize of
the latter are attributed to the different nature of the heavier E=O
bonds (E = Si–Pb), which exhibit higher zwitterionic character
E+–O- due to the significant decrease in electronegativity of
heavier elements and their intrinsic propensity to form weaker π-
bonds descending the group. Recent years have witnessed
considerable advances in the isolation of monomeric silacarbonyl
compounds including silanones (R2SiO) and silanoic acid
(RSi(O)OH) derivatives.[3-9] Rational steric and electronic
protection, Lewis base or Lewis base/acid complex formation are
the key approaches to achieve the required stabilization.[3-10]
Nevertheless, despite this success our knowledge about the
reactivity of silicon analogues of carbonyl compounds and their
synthetic potential remains to be very scarce.
Figure 1. (a) Silaformyl compounds I–IV. (b) Present work.
Among reported silacarbonyls, derivatives containing
a
complex (III) with a Si−O motif within coordination sphere of
tungsten, considered as a three-membered metallacycle rather
than a silaaldehyde π-complex.[8] More recently, the group of
Aldridge in an elegant study demonstrated the synthetic utility of
silaformyl group (-Si(H)O) are rare (I–IV, Figure 1a),[6-9] while a
stable analogue of an aldehyde (RSi(H)O) with three-coordinate
silicon is not known. Driess and co-workers reported
a
silaformamide–borane complex (I) with essential Si=O double
bond character synthesized by reacting corresponding
hydroxysilylene with water–borane adduct H2OB(C6F5)3.[6]
Several years later, Roesky, Frenking and co-workers described
the isolation of silaformyl chloride complex (II)[7] via the reaction
of the silylene dichloride–NHC adduct (IDipp)Cl2Si: with
H2OB(C6F5)3 and additional equivalent of the NHC. Hashimoto,
Tobita and co-workers isolated anionic 2-silaaldehyde
nacnac-supported chlorosilylene to access
a number of
silacarbonyls, including silaformamide IV.[9]
Previously we succeeded in the isolation of stable three-
coordinate imino(silyl) silanones [(IDipp)N](R3Si)SiO (IDipp =
[HC(DippN)]2C:, R = tBu, SiMe3) with prolonged lifetime in
solution.[3a] Our quest for a stable silaaldehyde started from the
investigation of the reactivity of a NHC-stabilized silyliumylidene
[(IMe4)2(MesTer)Si:]Cl (1, MesTer = 2,6-(2,4,6-Me3C6H2)2C6H3, IMe4
= [(Me)C(MeN)]2C:)[11] and hydridosilylene (IMe4)(tBu3Si)(H)Si:
(2).[12] These compounds react with carbon dioxide affording
NHC-stabilized silaacylium salt [(IMe4)2(MesTer)Si(O)][Cl] (3) with
comparably high double bond character of the Si=O bond,[5c] and
NHC-free cyclotrisiloxane [(tBu3Si)(H)SiO]3 regarded as a trimer
of silaaldehyde intermediate.[13] Exploration of the reactivity of
silyliumylidene (1) towards chalcogens and H2S enabled an
access to NHC-stabilized heavier chalcogen silaacylium
derivatives[14] and thiosilaaldehyde.[15] Herein, we report our study
devoted to the synthesis of a silaaldehyde, isolated as a Si,O-
donor-acceptor complex, and its unique reactivity showing strong
relationship to the chemistry of carbonyl congeners (Figure 1b).
[a]
[b]
D. Sarkar, Dr. V. Nesterov, P.J. Altmann, Prof. Dr. S. Inoue
WACKER-Institute of Silicon Chemistry and
Catalysis Research Center
Technische Universität München
Lichtenbergstraße 4, 85748 Garching bei München (Germany)
E-mail: s.inoue@tum.de
Dr. T. Szilvási
Department of Chemical and Biological Engineering
University of Wisconsin–Madison
1415 Engineering Drive, Madison, WI 53706-1607 (USA)
Supporting information for this article is given via a link at the end of
the document
This article is protected by copyright. All rights reserved.

10.1002/chem.201805604
Chemistry - A European Journal
COMMUNICATION
Treatment of sillyliumylidene complex 1 with equimolar
amounts of gallium chloride and water in acetonitrile at low
temperatures led to the formation of complex 4 together with
corresponding imidazolium chloride (Scheme 1). Recrystallization
of the row product from acetonitrile/toluene solution (2 : 1) at –
30°C furnished colorless crystals of 4 in a moderate yield (61 %).
bond is also elongated compared to those in I, II, and IV (1.552(2),
1.568(15), and 1.5514(10) Å, respectively)[6,7,9] and in three-
coordinate silanones (1.52–1.54 Å).[3]
In the solid state, the IR spectrum of 4 displayed a strong
absorption band at 975 cm-1. Although Si=O stretching vibrations
of parent silaaldehydes in argon matrix are observed at higher
wave numbers (H2SiO, 휈̃ = 1202 cm-1, and MeSi(H)O, 휈̃ = 1207
cm-1),[18a] this value is large enough to distinguish it from the
absorption of Si–O single bonds (휈̃ = 800–900 cm-1).[18b] Thus, the
structural and IR data suggest strong dominance of the
zwitterionic resonance structure 4B or equivalent Lewis structure
4C into the ground state of the molecule (Figure 3).
Scheme 1. Hydrolysis of silyliumylidene complex 1 in the presence and
absence of the Lewis acid (GaCl3).
Figure 3. Resonance structures of silaaldehyde 4.
1
DFT calculations at B97-D/def2-SVP level of theory showed a
good agreement between calculated metric parameters, the 29Si
NMR as well as IR data ( = –41.2 ppm, 휈̃ = 964 cm-1) of 4 and
the experimentally obtained data. HOMO and LUMO of 4 are
mainly located at the aryl ligand/chlorine atom and NHC
ligand/Si–CNHC σ* orbital/aryl ligand, respectively (Figure S22). No
indication of possible Si–O π-orbital was observed. Natural
charges of Si and O atoms (1.67 and –1.22, respectively) indicate
strong charge separation. Obtained Wiberg bond index (WBI),
and Mayer bond order (MBO) of the Si–O bond (0.74 and 1.21,
respectively) indicate a single bond with negligible double bond
character. The computed mechanism of formation of 4 includes
barrier-free protonation of 1 involving H2OGaCl3 complex and
following transformations toward 4 with low energy barriers
(Scheme S1).
The H NMR spectrum of compound 4 in CD3CN shows a
distinct signal of silicon-bound hydrogen at 4.98 ppm (1JSi,H
=
234.2 Hz). It lies within the range of values reported for silaformyl
compounds I, II (broad signals at 5.64 and 5.55 ppm,
respectively)[6,7] and III (4.29 ppm,1JSi,H = 190.6 Hz),[8] and
considerably upfield shifted compared to the formyl proton of the
corresponding aldehyde MesTerCHO (9.65 ppm).[16] The 29Si NMR
spectrum of 4 exhibits a resonance at –45.0 ppm, which is very
close to that of silaformyl chloride II (–49.8 ppm).[7]
The molecular structure of complex 4 was unambiguously
confirmed by single crystal X-ray diffraction analysis (Figure 2),
which revealed a distorted tetrahedral geometry of the silicon
atom.
Interestingly, the use of other Lewis acid reagents, such as
AlCl3, B(C6F5)3, BX3 (X = F, Cl, Br) or ZnX2 (X = F, Cl), instead of
gallium chloride in the reaction of 1 with water did not lead to any
selective transformation. In an attempt to procure an acceptor-
free silaaldehyde MesTer(IMe4)Si(H)O, hydrolysis of 1 was also
performed in the absence of any Lewis acid (Scheme 1). However,
it resulted in the formation of a mixture of unidentified products,
from which only sterically hindered spirosiloxane 5 was isolated
in 9.2 % yield. The structure of 5 was confirmed using multinuclear
NMR spectroscopy and single crystal X-ray diffraction analysis
(see SI). Attempt to remove the NHC from 4 using BPh3 at 80 °C
led to the isolation of the corresponding borane–NHC adduct and
unidentified decomposition products.
Figure 2. Molecular structure of 4. Hydrogen atoms except H1 are omitted for
clarity.
In order to access donor-acceptor complex of a silacarboxylic
acid (6), silaaldehyde complex 4 was reacted with water in the
presence of the NHC as a hydrogen scavenger (Scheme 2).
Reaction led to the formation of an unprecedented gallium
silacarboxylate complex (7) isolated in low yield (8 %) if one
equivalent of the NHC was employed. The yield of 7 was
The Si–O bond distance in 4 is 1.605(3) Å. Surprisingly, it is
only marginally shorter than Si–O single bonds in acyclic
organodisiloxanes (R3Si)2O (1.61–1.64 Å) or siloxanes R3SiOR’
(ca. 1.64 Å), and even slightly longer than those in
halogenodisiloxanes (X3Si)2O (1.58–1.59 Å, X = F, Cl).[17] This
improved to 22
% using two equivalents of the NHC.
Corresponding 2,2-dihydroimidazolidine and imidazolium salt
This article is protected by copyright. All rights reserved.

10.1002/chem.201805604
Chemistry - A European Journal
COMMUNICATION
were identified as by-products. Additionally, alcoholysis of
complex 4 with tert-butanol provided silaacetal 8 isolated in 79 %
yield (Scheme 2).
nucleophilic attack of the silicon of 4 by the oxygen of H2O·NHC
complex (Scheme S2).
We used reaction of silaaldehyde complex 4 with an excess
of gallium chloride to access novel silaaroyl chloride 9 (Scheme
3). Analytically pure sample of 9 was obtained in low yield (9 %)
as a very moisture sensitive solid with low solubility in polar and
non-polar solvents. All attempts to characterize single crystals of
9 led to their contamination with the corresponding acid
Ar(IMe4)Si(O)(GaCl3)OH (10) due to partial hydrolysis.
In order to examine a relationship to classical acyl transfer
reactions, we performed hydrolysis of silaacyl derivatives 9 and 3
with water under various conditions. It was found, that reaction of
silaaroyl chloride 9 with water in the presence of NHC leads to
selective formation of siladicarboxylate dimer 7, while the reaction
of silaacylium salt 3[5c] with a NHC/GaCl3/H2O mixture (1:1:1)
provides the same product in 43 % yield (Scheme 3).
Scheme 2. Synthesis of siladicarboxylate 7 and silaacetal 8.
Molecular structures of 7 and 8 were confirmed using X-ray
diffraction analysis. In the solid state, compound 7 exists as a
centrosymmetric
(
dimer
containing
two
silacarboxylate
MesTerSiO2) fragments bridged by two GaCl2 units in a similar
manner found in gallium(III) carboxylate complexes (Figure 4).[19]
Each silicon center has a distorted tetrahedral geometry. The Si1–
O2 (1.586(17) Å) and Si1–O1 (1.603(17) Å) bond distances are
close to each other and to the Si–O distance found in 4. These
distances are also comparable to those in the donor-acceptor-
stabilized silanoic acid (EtO)(D→)Si(O→A)OH (1.588(2)–
1.626(2) Å) reported by Baceiredo, Kato and co-workers.[5e]
Moreover, both Si–O bonds in 4 are sufficiently shorter than Si–O
single bonds in gallium–siloxane complexes (1.62–1.70 Å).[20]
Scheme 3. Synthesis of silaacyl chloride complex 9 and alternative approaches
to siladicarboxylate complex 7.
Aldehydes and ketones are known as important reagents not
only in C–C bond forming reactions, but also for the construction
of mono- and heteronuclear C=E double bonds (E = C, N, P).[1]
We found, that reaction of 4 with tris(trimethylsilyl)phosphine at
elevated temperature in fluorobenzene yields selectively
thermally stable NHC-supported phosphasilene 11 (Scheme 4).
While the mechanism of this transformation remains unclear, it
may involve nucleophilic attack of the phosphorus reagent on the
electropositive silicon, leading to elimination of transient
[TMSOGaCl3] anion and following formation of TMSOGaCl2
dimer,[22] TMSCl, and phosphasilene 11 (Scheme S3). Notably,
analogous
reaction
of
aldehydes
RCHO
with
bis(trimethylsilyl)phosphines R’PTMS2 in the presence of AlCl3 is
known to yield corresponding phosphaalkenes R(H)C=PR’.[21]
Figure 4. Molecular structure of 7. Hydrogen atoms are omitted for clarity.
According to our DFT calculation, the Si–O bonds in SiO2
moieties in 7 are almost identical within 0.02 Å. MBOs are same
for all Si–O bonds (1.18) and the same as found in the starting
material. Noteworthy, HOMO–40 of 7 (Figure S24) shows a cyclic
delocalization through the oxygen atoms, thus supporting the
heavy silacarboxylate analogy. Conversion of 4 into 7 involves
intermediate formation of the acid 6 and starts from the
Scheme 4. Synthesis of phosphasilene 11 from silaaldehyde complex 4.
The same phosphasilene complex 11 was obtained
alternatively using a convenient two-step approach starting from
This article is protected by copyright. All rights reserved.

10.1002/chem.201805604
Chemistry - A European Journal
COMMUNICATION
MesTerSi(H)Cl2 (see SI). Reaction products in both cases were
identical and showed same spectroscopic data. Moreover, 11 was
characterized by X-ray diffraction analysis (Figure 5). Obtained
spectroscopic and structural data of 11 are in good agreement
with those of the described previously similar phosphasilene–
NHC complex bearing more bulky DippTer aryl substituent at the
silicon atom.[23,24]
Filippou, B. Baars, O. Chernov, Y. N. Lebedev, G. Schnakenburg, Angew.
Chem. Int. Ed. 2014, 53, 565; Angew. Chem. 2014, 126, 576.
Silanones with four-coordinate silicon: a) R. Rodriguez, T. Troadec, D.
Gau, N. Saffon‐Merceron, D. Hashizume, K. Miqueu, J. M. Sotiropoulos,
A. Baceiredo, T. Kato, Angew. Chem. Int. Ed. 2013, 52, 4426; Angew.
Chem. 2013, 125, 4522; b) Y. Xiong, S. Yao, R. Müller, M. Kaupp, M.
Driess, Nat. Chem. 2010, 2, 577; c) S. Yao, Y. Xiong, M. Driess, Chem.
Eur. J. 2010, 16, 1281; d) Y. Xiong, S. Yao, R. Müller, M. Kaupp, M.
Driess, J. Am. Chem. Soc. 2010, 132, 6912; e) Y. Xiong, S. Yao, M.
Driess, J. Am. Chem. Soc. 2009, 131, 7562.
[4]
[5]
a) R. Rodriguez, I. Alvarado-Beltran, J. Saouli, N. Saffon‐Merceron, A.
Baceiredo, V. Branchadell, T. Kato, Angew. Chem. Int. Ed. 2018, 57,
2635; Angew. Chem. 2018, 130, 2665; b) R. Rodriguez, D. Gau, J. Saouli,
A. Baceiredo, N. Saffon‐Merceron, V. Branchadell, T. Kato, Angew.
Chem. Int. Ed. 2017, 56, 3935; Angew. Chem. 2017, 129, 3993; c) S. U.
Ahmad, T. Szilvási, E. Irran, S. Inoue, J. Am. Chem. Soc. 2015, 137,
5828; d) Y. Wang, M. Chen, Y. Xie, P. Wie, H. F. Schaefer III, P. v. R.
Schleyer, G. H. Robinson, Nat. Chem. 2015, 7, 509; e) R. Rodriguez, D.
Gau, T. Troadec, N. Saffon‐Merceron, V. Branchadell, A.; Kato, T.
Baceiredo, Angew. Chem. Int. Ed. 2013, 52, 8980; Angew. Chem. 2013,
125, 9150; f) R. S. Ghadwal, R. Azhakar, H. W. Roesky, K. Pröpper, B.
Dittrich, S. Klein, G. Frenking, J. Am. Chem. Soc. 2011, 133, 17552-
17555; g) Y. Xiong, S. Yao, M. Driess, Angew. Chem. Int. Ed. 2010, 49,
6642; Angew. Chem. 2010, 122, 6792; h) Y. Xiong, S. Yao, M. Driess,
Dalton Trans. 2010, 39, 9282; i) S. Yao,Y. Xiong, M. Brym, M. Driess, J.
Am. Chem. Soc. 2007, 129, 7268,
Figure 5. Molecular structure of 11. Hydrogen atoms except H1 are omitted for
clarity.
[6]
[7]
[8]
[9]
S. Yao, M. Brym, C. V. Wüllen, M. Driess, Angew. Chem. Int. Ed. 2007,
46, 4159; Angew. Chem. 2007, 119, 4237.
In summary, we have synthesized and characterized the first
donor-acceptor complex of an aryl silaaldehyde. Notably, it reacts
as masked silacarbonyl providing an access to a number of stable
derivatives, thus showing a relationship to carbonyl chemistry.
Difficulties in the preparation of the corresponding donor, and
acceptor-free silaaldehyde complexes, as well as the isolation of
free spirosiloxane underline low stability of the corresponding free
silaaldehyde. Thus, the quest for stable free silaaldehydes
remains challenging.
R. S. Ghadwal, R. Azhakar, H. W. Roesky, K. Propper, B. Dittrich, C.
Goedecke, G. Frenking, Chem. Commun. 2012, 48, 8186.
T. Fukuda, H. Hashimoto, S. Sakaki, H. Tobita, Angew. Chem. Int. Ed.
2016, 55, 188.
S. Aldridge, D. Do, A. Protchenko, M. Angeles Fuentes, J. Hicks, E.
Kolychev, P. Vasko, Angew. Chem. Int. Ed. 2018, 57, 13907; Angew.
Chem. 2018, 130, 14103.
[10] V. Nesterov, D. Reiter, P. Bag, P. Frisch, R. Holzner, A. Porzelt, S. Inoue,
Chem. Rev. 2018, 118, 9678.
[11] S. U. Ahmad, T. Szilvási, S. Inoue, Chem. Commun. 2014, 50, 12619.
[12] S. Inoue, C. Eisenhut, J. Am. Chem. Soc. 2013, 133, 18315.
[13] C. Eisenhut, N. C. Breit, T. Szilvási, E. Irran, S. Inoue, Eur. J. Inorg.
Chem. 2016, 2696.
Acknowledgements
[14] D. Sarkar, D. Wendel, S. U. Ahmad, T. Szilvási, A. Pothig, S. Inoue,
Dalton Trans. 2017, 46, 16014.
We gratefully acknowledge financial support from WACKER
Chemie AG, the European Research Council (SILION 637394),
the DAAD (fellowship for D.S.), Dr. A. Pöthig for crystallographic
advice, Mr. J. Sicklinger for IR measurements.
[15] A. Porzelt, J. Schweizer, R. Baierl, P. Altmann, M. Holthausen, S. Inoue,
Inorganics 2018, 6, 54.
[16] R. C. Smith, L. B. Gleason, J. D. Protasiewicz, J. Mater. Chem. 2006, 16,
2445.
[17] W. S. Sheldrick in The Chemistry of Organic Silicon Compounds (Eds.:
S. Patai, Z. Rappoport), John Wiley & Sons, Ltd, Chichester, 1989, pp.
227–303.
Keywords: Silaaldehyde • Silanone • Silacarbonyl group •
Silyliumylidene • N-Heterocyclic carbene
[18] a) R. Withnall, L. Andrews, J. Am. Chem. Soc. 1986, 108, 8118; b) V. N.
Khabashesku, Z. A. Kerzina, K. N. Kudin, O. M. Nefedov, J. Organomet.
Chem. 1998, 566, 45.
[1]
[2]
J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd ed., Oxford
Press, Oxford, 2012.
[19] M. R. Kaluđerović, S. Gómez-Ruiz, B. Gallego, E. Hey-Hawkins, R.
Paschke, G. N. Kaluđerović, Eur. J. Med. Chem. 2010, 45, 519.
[20] a) C. N. McMahon, S. J. Obrey, A. Keys, S. G. Bott, A. R. Barron, Dalton
Trans. 2000, 2151; b) N. R. Bunn, S. Aldridge, C. Jones, Appl.
Organomet. Chem. 2004, 18, 425.
a) Y. Xiong, S. Yao, M. Driess, Angew. Chem. Int. Ed. 2013, 52, 4302;
Angew. Chem. 2013, 125, 4398; b) S. S. Sen, Angew. Chem. Int. Ed.
2014, 53, 8820; Angew. Chem. 2014, 126, 8964.
[3]
Ambient temperature stable silanones with three-coordinate silicon: a) D.
Wendel, D. Reiter, A. Porzelt, P. J. Altmann, S. Inoue, B. Rieger, J. Am.
Chem. Soc. 2017, 139, 17193; b) A. Rosas‐Sánchez, I. Alvarado‐Beltran,
A. Baceiredo, N. Saffon‐Merceron, S. Massou, D. Hashizume, V.
Branchadell, T. Kato, Angew. Chem. Int. Ed. 2017, 56, 15916; Angew.
Chem. 2017, 129, 16132; c) I. Alvarado‐Beltran, A. Rosas‐Sánchez, A.
Baceiredo, N. Saffon‐Merceron, V. Branchadell, T. Kato, Angew. Chem.
Int. Ed. 2017, 56, 10481; Angew. Chem. 2017, 129, 10617; d) A. C.
[21] J. I. Bates, B. O. Patrick, D. P. Gates, New. J. Chem. 2010, 34, 1660.
[22] H. Schmidbaur, W. Findeiss, Chem. Ber. 1966, 99, 2187.
[23] K. Hansen, T. Szilvási, B. Blom, M. Driess, Angew. Chem. Int. Ed. 2015,
54, 15060; Angew. Chem. 2015, 127, 15274.
[24] V. Nesterov, N. C. Breit, S. Inoue, Chem. Eur. J. 2017, 23, 12014.
This article is protected by copyright. All rights reserved.

10.1002/chem.201805604
Chemistry - A European Journal
COMMUNICATION
COMMUNICATION
First silicon analogue of an
aldehyde stabilized with an external
Lewis base and Lewis acid was
Debotra Sarkar, Vitaly Nesterov, Tibor
Szilvási, Philipp J. Altmann, Shigeyoshi
Inoue*
successfully
isolated
and
Page No. – Page No.
characterized. It shows unique
reactivity mimicking behaviour of
carbonyl congeners and provides an
access to various classes of
silacarbonyl derivatives.
The Quest for Stable Silaaldehydes:
Synthesis and Reactivity of a Masked
Silacarbonyl
This article is protected by copyright. All rights reserved.