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evaporation to dryness, the residue was purified by silica gel
column chromatography using petroleum ether/ethyl acetate
(2/1) as eluent. Colourless oil (520 mg, 0.99 mmol, 35% yield).
1H NMR (300 MHz, CDCl3, ppm): δ = 4.43–4.46 (m, 4 H, CH2),
7.15–7.34 (m, 20 H, Ar). 13C{1H} NMR (75 MHz, CDCl3, ppm): δ =
67.1 (dd, JCP = 5.7 Hz, JCP = 7.7 Hz, 2 C, CH2), 120.1 (d, JCP = 4.8
Hz, 8 C, Ar), 125.6 (d, JCP = 1.1 Hz, 4 C, Ar), 129.9 (8 C, Ar), 150.4
(d, JCP = 7.2 Hz, 4 C, Ar). 31P NMR (202 MHz, CDCl3, ppm): δ = -
12.0 (s, 2 P). IR–UATR (oil, cm-1): 3069, 2956, 1486, 1285, 1184,
947, 933, 752. HRMS (APCI–ASAP): m/z calcd for C26H25O8P2
[M+H]+ 527.1019; found 527.1019.
Notes and references
1
2
3
4
H. Horiguchi, H. Tsurugi, T. Satoh andDMO.I:M10i.1u0r3a9,/AC7dNvJ. 0S0y5n6t6hK.
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In some studies, phosphotriesters were used as proligands
which were converted into anionic phosphorous salts linked
to the metal centres. a) D. Gong, W. Dong, Y. Hu, J. Bi, X. Zhang
and L. Jiang, Polymer, 2009, 50, 5980; b) W. Pan, H. Chen, R.
Sun, D. Gong, X. Jia, Y. Hu and X. Zhang, Ind. Eng. Chem. Res.,
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M. Menzel and U. Kragl, J. Polym. Sci. Pol. Chem., 2007, 45
,
General procedure for hydrosilylation of ketones
3032; d) J. Otera, Y. Niibo, N. Tatsumi and H. Nozaki, J. Org.
Chem., 1988, 53, 275; e) J. Otera, Y. Niibo and H. Nozaki,
Tetrahedron, 1991, 47, 7625.
K. P. Kepp, Inorg. Chem., 2016, 55, 9461.
For recent publications see: a) C. Boone, I. Korobkov and G. I.
Nikonov, ACS Catal., 2013, 3, 2336; b) A. Rit, A. Zanardi, T. P.
In a flame-dried round-bottom flask, to a solution of TPP (16 mg,
0.05 mmol) in dry THF (2 mL) under an atmosphere of argon was
5
6
added ZnEt2 (50
µL, 1 M solution in n-hexane, 0.05 mmol). After
10 min, the ketone (1 mmol) and (EtO)2MeSiH (252
µL, 1.5
Spaniol, L. Maron and J. Okuda, Angew. Chem. Int. Ed., 2014,
53, 13273; c) P. A. Lummis, M. R. Momeni, M. W. Lui, R.
McDonald, M. J. Ferguson, M. Miskolzie, A. Brown and E.
Rivard, Angew. Chem. Int. Ed., 2014, 53, 9347; d) Z. Mou, H.
Xie, M. Wang, N. Liu, C. Yao, L. Li, J. Liu, S. Li and D. Cui,
Organometallics, 2015, 34, 3944; e) W. Sattler, S. Ruccolo, M.
Rostami Chaijan, T. Nasr Allah and G. Parkin, Organometallics,
2015, 34, 4717; f) K. Junge, K. Möller, B. Wendt, S. Das, D.
mmol) were injected and the reaction was stirred overnight at
room temperature. After removal of the solvent under reduced
pressure, MeOH (4 mL) and an aqueous 1 N NaOH solution (4
mL) were added and the resulting solution was stirred for 12 h.
The reaction medium was quenched with an aqueous 1 N HCl
solution (10 mL) and brine (10 mL), and extracted with Et2O (3 x
10 mL). The combined organic layers were washed with an
aqueous 1 N NaOH solution (10 mL) and brine (10 mL). After
drying over anhydrous MgSO4, filtration and evaporation to
dryness, the residue was submitted to 1H NMR analysis to
determine the conversion. The crude product was then purified
by silica gel column chromatography using petroleum
ether/Et2O mixtures. 1H and 13C NMR data for purified products
are provided in the ESI and are in agreement with reported
values.
Gördes, K. Thurow and M. Beller, Chem. Asian J., 2012, 7, 314;
g) S. Liu, J. Peng, H. Yang, Y. Bai, J. Li and G. Lai, Tetrahedron,
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S. Pang, J. Peng, J. Li, Y. Bai, W. Xiao and G. Lai, Chirality, 2013,
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Chem. Soc., 2016, 138, 12332; b) H. Pellisier, Tetrahedron,
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a) B. Xiong, Q. Ye, X. Feng, L. Zhu, T. Chen, Y. Zhou, C.-T. Au
and S.-F. Yin, Tetrahedron, 2014, 70, 9057; b) B. Xiong, X. Feng,
L. Zhu, T. Chen, Y. Zhou, C.-T. Au and S.-F. Yin, ACS Catal., 2015,
6, 53358; n) M.
General procedure for diethylzinc addition to aldehydes
8
In
bisphosphate
an atmosphere of argon were added Ti(Oi-Pr)4 (180
a
flame-dried round-bottom flask, to
(16 mg, 0.025 mmol) in dry toluene (2 mL) under
L, 0.6
a solution of
7
8
3
µ
mmol) and ZnEt2 (1 mL, 1 M solution in n-hexane, 1 mmol). After
10 min, the aldehyde (0.5 mmol) was injected and the reaction
was stirred overnight at room temperature. The reaction
medium was quenched with an aqueous 1 N HCl solution (8 mL)
and extracted with CH2Cl2 (3 x 10 mL). The combined organic
layers were washed with an aqueous 1 N HCl solution (10 mL)
and water (10 mL). After drying over anhydrous MgSO4,
filtration and evaporation to dryness, the residue was purified
by silica gel column chromatography using petroleum
ether/Et2O mixtures. 1H and 13C NMR data for purified products
are provided in the ESI and are in agreement with reported
values.
5
, 537.
H. Vignesh Babu and K. Muralidharan, Polymer, 2014, 55, 83.
only supported by 1H and 31P NMR analyses (δp
9
10 Synthesis of
4
= - 17.4 ppm) has already been described by reaction between
ethylene glycol, (PhO)2P(O)Cl, and a base. In our hands, this
protocole only gave rise to mixtures of TPP (δp = - 17.7 ppm)
and ethylene glycol by-products. See: C. Nguyen and J. Kim,
Polym. Degrad. Stab., 2008, 93, 1037.
11 CCDC 1526882 contains the crystallographic data for this
paper. These data can be obtained free of charge from the
Cambridge Crystallographic Data Centre.
12 Conversions with 1.5 mmol of PMHS were as follow: 5b, 48%;
5c, 85%; 5g, >99%; 5h, 53%; 5k, no reaction; 5l, 89%.
Acknowledgements
We thank Université de Rennes 1 and CNRS for financial
support, and FEDER funds for acquisition of single crystal
equipment.
4 | J. Name., 2012, 00, 1-3
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