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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry Supporting Information For Reduction of Nitriles into Aldehydes Using Calcium ypophosphite and Nickel Precursor Rim Mouselmani, [a] [b] Ali achem, [b] Ali Alaaeddine, [b] Estelle Métay, [a] and Marc Lemaire [a] [a] Equipe Catalyse Synthèse et Environnement, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS, UMR, Université Claude Bernard Lyon, Bâtiment Curien, boulevard du novembre, F Villeurbanne Cedex, France Fax: + () ;Tel: + () ; estelle.metay@univ-lyon.fr, Fax: + () ; phone: + () ; marc.lemaire.chimie@univ-lyon.fr [b] Laboratoire de Chimie Médcinale et des Produits Naturels (LCMPN), Université Libanaise (UL), Beyrouth Faculté des Sciences, Campus de Rafik ariri adath, Beyrouth, Liban Tel : + () ; ahachem@ul.edu.lb. General information All reagents were obtained from commercial sources and used as received. CuCl (ref: ) and Ca( P ) (ref: ), TDA (ref: L) were purchased from Alfa Aesar and the second was placed always in desiccator. Ni(Ac). Assay.% (KT) (ref: ) was purchased from Fluka. % Pd/C (ref: -), % Pt/C (ref: -), % Pd/C (ref: - ), [RuCl (p-cymene)] (ref: -), NiCp (ref: -) were purchased from Strem Chemicals. NiBr (ref: ), Ni (acac) (ref: ), Ni(Ph P) Br (ref: ), Ni(Ph P) (ref : ), Ni(cod) (ref: ), Ni~ wt. % on Si /Al (ref: ),, - bipyridine (ref: D) were purchased from Sigma Aldrich. Ni(dppe)Cl (Catalog no. ) was purchased from ACRS. NiCl (ref: ) was purchased from Laurylab. The complete references of the used sealed tubes are: ACE pressure tubes, Ace-Thred #, order code (Z), length (. cm), body.d. ( mm), capacity ( ml), pressure rating (
2 PSI or. bar). The pressure tube was closed by a front seal Ace -rings, Silicone (wall. mm, I.D.. mm) provided by Sigma Aldrich (ref: ). Silica gel ( micron) was used for column chromatography. Thin layer chromatography was performed on precoated silica gel F plates. UV light,,-dinitrophenylhydrzine was used for analysis of the TLC plates. All compounds were characterized by spectroscopic data. The nuclear magnetic resonance (NMR) spectra were recorded either on a Bruker ALS ( : Mz, C: Mz), a DRX ( : Mz, C: Mz) or a Bruker DRX ( : Mz, C: Mz) spectrometer, in CDCl or DMS-d at K. Chemical shifts are reported in parts per million (ppm) and are calibrated on residual solvent peaks: CDCl. ppm in and. ppm in C, or DMS-d. ppm in and. ppm in C. Spin-spin coupling constants (J) are given in z. The peak patterns are indicated as follows: (s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet, and br. for broad). GC-MS analyses were performed on a DSQ - Thermofinnigan spectrometer equipped with quadrupole analyzer and a DB-MS capillary column (. m.mm.µm). The carrier gas was helium, at a flow rate of ml/min. Column temperature was initially C for min, then gradually increased to C at C/min and finally kept at C for min. The injector temperature was C and the transfer line temperature was C. GC analyses were performed on a Shimadzu Gas Chromatograph GC equipped with a ZB--MS column (. m.mm.µm). The carrier gas was N at a flow rate of. ml/min. Column temperature was initially C for min, then gradually increased to C at C/min and finally kept at C for min. The injector temperature was C and for detection a FID was used at C.
3 . General procedure Procedure for the reduction of nitrile into aldehyde In a sealed tube, Nickel(II)acetate tetrahydrate (. mg,. mmol, mol%) was introduced followed by water ( ml, [Ca( P ) ]= M), the tube was stirred at room temperature. Calcium hypophosphite ( mg, mmol) was then added followed by calcium acetate monohydrate (. mg,. mmol, mol%). To this mixture was added the nitrile substrate ( mmol) and ethanol absolute ( ml, [nitrile] in ethanol= M), the tube was then sealed. The reaction mixture was stirred at rpm and heated at C. After the sufficient time for each substrate, the tube was cooled at room temperature, depressurized and an aliquot was taken and extracted with water and methylene chloride, diethyl ether or pentane for GC analysis to check the conversion of the starting material. The reaction mixture was then diluted by excess of water to remove ethanol and extracted with pentane, diethyleher or methylene chloride. The combined organic extracts were dried with Na S, filtered and concentrated under reduced pressure ( mbar). After concentration, aldehydes were obtained as oils or solids. If needed a flash chromatography column was done on silica gel by using gradient of different solvents according to the final product. The conversion of the nitrile was determined by GC corresponding to -(the area of nitrile peak) The products were characterized by NMR spectroscopy.. Characterization Chemical Formula: C Molecular Weight:. Benzaldehyde [--] Colorless oil. Eluent for isolation: : pentane/c Cl. NMR ( Mz, CDCl ): δ. (s,, C),. (d, J=. z,, C Ar ),.-. (m,, C Ar ),.-. (m,, C Ar ) ppm C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. (C q, C Ar ),. ( C, C Ar ),. (C, C Ar ) ppm. GC: retention time:. min. Chemical Formula: C Molecular Weight:.
4 Chemical Formula: C Molecular Weight:. -ydroxy benzaldehyde [--] ffwhite powder. Eluent for isolation: : C Cl /diethylether. NMR ( Mz, DMS-d ): δ. (s broad,, ),. (s,, C),. (d, J=. z,, C Ar ),. (d, J=.z,, C Ar ), ppm. C NMR ( Mz, DMS-d ): δ. (C q, C-C=),. (C q, C Ar ),. (C, C Ar ),. (C q, C Ar ),. (C, C Ar ) ppm. GC: retention time:. min. -ydroxy benzaldehyde [-] Colorless liquid. Eluent for isolation: : pentane/diethylether. NMR ( Mz, CDCl ): δ. (s,, ),. (s,, C),.-. (m,, C Ar ),.-. (m,, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C q, C Ar ),. (C, C Ar ),. (C, C Ar ) ppm. GC: retention time:. min. Me Chemical Formula: C Molecular Weight:, -methoxybenzaldehyde [--] Colorless liquid. NMR ( Mz, CDCl ): δ. (s,, C),. (d, J =. z,, C Ar ),. (d, J =. z,, C Ar ),. (s,, C ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),.( C, C Ar ),. (C q, C Ar ),. ( C, C Ar ),. (C ) ppm. GC: retention time:. min. Chemical Formula: C Molecular Weight:. Ethyl - formyl benzoate [--] Colorless liquid. NMR ( Mz, CDCl ): δ. (s,, C),.-. (m,, C Ar ),. (d, J =. z,, C Ar ),. (d, J =. z,, C Ar ),. (q, J =. z, C ),. (t, J =. z,, C ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C-C=),. (C q, C Ar ),. (C q, C Ar ),. ( C, C Ar ),. ( C, C Ar ),. (C ),. (C ) ppm. GC: retention time:. min. Chemical Formula: C Molecular Weight:. -methyl benzaldehyde [--] Colorless liquid. Eluent for isolation: : pentane/diethylether. NMR ( Mz, CDCl ): δ. (s,, C),.-. (dd,, C Ar ),.-.(d, J =. z,, C Ar ),. (s,, C ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. ( C, C Ar ),. (C q, C Ar ),. ( C, C Ar ),. (C ) ppm. GC: retention time:. min.
5 F C Chemical Formula: C F Molecular Weight:. -(Trifluoromethyl) benzaldehyde [--] Light yellow liquid. Eluent for isolation: : pentane/diethylether. NMR ( Mz, CDCl ): δ. (s,, C),. (d, J =. z,, C Ar ),. (d, J =. z,, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. ( C, C Ar ),. ( C, C Ar ),. (C q, CF ),. (C q, C Ar ) ppm. GC: retention time:. min. Chemical Formula: C Molecular Weight:. -Naphthalaldehyde [--] Slight yellow crystalline powder. Eluent for isolation: : C Cl /diethylether. NMR ( Mz, CDCl ): δ. (s,, C),. (s,, C Ar ),.-. (m,, C Ar ),.-. (m,, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. (C, C Ar ),. ( C q, C Ar ),. (C q, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ) ppm. GC: retention time:. min. Chemical Formula: C Molecular Weight:. -Naphthalaldehyde [-] Colorless liquid. Eluent for isolation: : C Cl /diethylether. NMR ( Mz, CDCl ): δ. (s,, C),. (d,, J =. z, C Ar ),. (d,, J =. z, C Ar ),. (d,, J =. z, C Ar ),. (d,, J =. z, C Ar ),.-. (m,, xc Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C),. (C, C Ar ),. (C, C Ar ),. (C q, C Ar ),. (C q, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ) ppm. GC: retention time:. min. Chemical Formula: C Molecular Weight:, Terephthaldehyde [-] White crystals. Eluent for isolation: : pentane/diethylether. NMR ( Mz, CDCl ): δ. (s,, C),. (s,, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. ( C q, C-C=),. ( C q, C Ar ),. ( C, C Ar ) ppm. GC: retention time:. min.
6 Cl Chemical Formula: C Cl Molecular Weight:, -Chlorobenzaldehyde [--] Colorless Liquid. Eluent for isolation: only pentane. NMR ( Mz, CDCl ): δ. (s,, C-C-),. (s,, C Ar ),.-. (m,, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. (C, C Ar ),. (C q, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ) ppm. GC: retention time:. min. Br Chemical Formula: C Br Molecular Weight:, -Bromobenzaldehyde [--] Yellow liquid. Eluent for isolation: : pentane/c Cl. NMR ( Mz, CDCl ): δ. (s,, C),. (s,, C Ar ),.-. (m,, C Ar ),.-. (m,, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C, C Ar ),. (C q, C Ar ) ppm. GC: retention time:. min. Br Chemical Formula: C Br Molecular Weight:, -Bromobenzaldehyde [--] White crystals. Eluent for isolation: : pentane/c Cl. NMR ( Mz, CDCl ): δ. (s,, C),. (d,, J =. z, C Ar ),. (d,, J =. z, C Ar ) ppm. C NMR ( Mz, CDCl ): δ. (C q, C-C=),. (C q, C Ar ),. (C, C Ar ),. ( C, C Ar ),. (C q, C Ar ) ppm. GC: retention time:. min.. Spectra
7 Benzaldehyde [--] (b) - -E+ E+ E+ E+ E+ E+ E E+ E+ E+ E+ E+ E+ E+ E+ E
8 -ydroxy benzaldehyde [--] - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E E+ E+ E+ E+ E+ E+ E
9 -ydroxy benzaldehyde [-] (b) - -E+ E+ E+ E+ E+ E+ E E+ -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E
10 -Methoxy benzaldehyde [--] (b) - E+ E+ E E+ E+ E+ E+ E
11 Ethyl -formylbenzoate [--] (b) - - E+ E+ E+ E+ E+ E+ E Methyl benzaldehyde [--] (b) - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E
12 - -E+ E+ E+ E+ E+ E+ E (Trifluoromethyl)benzaldehyde [--] (b) - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E F C
13 - -E+ E+ E+ E+ E+ E+ E+ E+ E Naphthaldehyde [--] (b) - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E F C
14 - -E+ E+ E+ E+ E+ E+ E+ E Naphthaldehyde [-] (b) - E+ E+ E+ E+ E+ E+ E
15 - -E+ E+ E+ E+ E Terephthaldehyde [-] - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+.....
16 - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E Chlorobenzaldehyde [--] - E+ E+ E+ E+ E+ E+ E+ E Cl
17 - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E Bromobenzaldehyde [--] - E+ E+ E+ E+ E+ E+ E+ E Cl Br
18 - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E Bromobenzaldehyde [--] - -E+ E+ E+ E+ E+ E+ E+ E Br Br
19 - -E+ E+ E+ E+ E+ E+ E+ E+ E+ E+ E Br
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