Supporting Information. Deprotonative metalation of five-membered aromatic heterocycles using mixed. lithium-zinc species
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1 Supporting Information Deprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species Jean-Martial L'Helgoual'ch, Anne Seggio, Floris Chevallier, Mitsuhiro Yonehara, Erwann Jeanneau, Masanobu Uchiyama,*, and Florence Mongin*, Synthèse et ElectroSynthèse Organiques, UMR 6510 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, Rennes, France The Institute of Physical and Chemical Research, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama , Japan Centre de Diffractométrie Henri Longchambon, Université Claude Bernard Lyon 1, Villeurbanne, France Table of Contents Page S1 S2 S3 Item Table of Contents General Procedures Cartesian Coordinates and Total Electron Energies S18 X-ray diffraction analysis of compound 17 S19 1 H and 13 C NMR spectra for compounds 2, 4, 6, 8, 10, 12, 14, 16, 17, 18 and 19 S1
2 General Procedures. All reactions were performed under argon atmosphere. THF was distilled over sodium/benzophenone and hexane was distilled after drying over P 4 O 10. Nuclear magnetic resonance spectra were acquired on Bruker ARX-200 (200 MHz and 50 MHz for 1 H and 13 C respectively) and Bruker AC-300 (300 MHz and 75 MHz for 1 H and 13 C respectively) spectrometers. Chemical shifts are given in ppm as values relative to tetramethylsilane ( 1 H, 13 C) and coupling constants are given in Hz. High resolution mass spectra measurements were performed at the CRMPO in Rennes (Centre Régional de Mesures Physiques de l Ouest) using a Micromass MS/MS ZABSpec TOF instrument in EI mode. Liquid chromatography separations were achieved on silica gel Merck Geduran Si 60 (40 63 mesh). S2
3 Cartesian Coordinates and Total Electron Energies. Figure 1_Li. E N 1.30 N O 1.86 Li RT O 2.44 Li TS 22.9 N O 1.74 Li PD RT_Li HF= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S3
4 TS_Li HF= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z PD_Li HF= S4
5 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Figure 1_ZnCl. E N O ZnCl N O ZnCl TS N O 1.89 ZnCl PD RT RT_ZnCl HF= S5
6 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z TS_ZnCl HF= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S6
7 PD_ZnCl HF= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S7
8 Figure 2. N = TMP G = -12 kcal/mol 2.00 LiTMP + Me 2 Zn Me Zn N Me 1.89 Li LiTMP 2.15 G = +3.8 kcal/mol (TMP) 2 Zn N Zn N 1.95 Li 96.9 N LiTMP Sum of electronic and thermal Free Energies= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S8
9 Me 2 Zn Sum of electronic and thermal Free Energies= S9
10 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z (TMP) 2 Zn Sum of electronic and thermal Free Energies= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S10
11 S11
12 (TMP)ZnMe 2 Li Sum of electronic and thermal Free Energies= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S12
13 S13
14 (TMP) 3 ZnLi Sum of electronic and thermal Free Energies= Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S14
15 S15
16 S16
17 S17
18 X-ray diffraction analysis. ORTEP figure N I S I 17 Crystal data 17: C3HI2NS; Mr = ; T = 295 K; = Å; monoclinic; space group P21/c, a = 7.363(4) Å, b 3-3 = (1) ; V = 707.8(5) Å ; Z = 4; Dc = Mg m ; µ = 9.07 = (6) Å, c = 7.998(1) Å, mm-1; F(000) = 592; crystal size = 0.08 x 0.09 x 0.13 mm; limiting indices: 0 h 9, -17 k 17, -10 l range for data collection: , 9; 3390 reflections collected; 1720 reflections unique (Rint = 0.079); R1(I>2 (I))=0.058; wr2(i>2 (I))= 0.067; Crystallographic data were deposited in CSD under CCDC registration number S18
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