Supporting Information. A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions

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1 Supporting Information A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions Thomas Di Franco, Marko Stojanovic, Sébastien Keller, Rosario Scopelliti, and Xile Hu* Laboratory of Inorganic Synthesis and Catalysis Institute of Chemical Sciences and Engineering Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305 Lausanne, CH 1015, Switzerland xile.hu@epfl.ch S1

2 1. X-Ray Crystallography The diffraction data were measured at low temperature [140(2) K] by using Mo or Cu Kα radiation on an Agilent Technologies SuperNova dual system in combination with an Atlas CCD detector. The crystal structures were refined using full-matrix least-squares based on F2 with all non-hydrogen atoms anisotropically defined. Hydrogen atoms were placed in calculated positions by means of the riding model. Crystallographic details for [( Pyr N 2 N)NiCl] (3) A total of reflections (-11 h 11, -10 k 15, -19 l 19) were collected at T = 140(2) K of which 3543 were unique [R(int) = ]; Cu Kα radiation (λ= Å). The structure was solved by the direct methods. All non-hydrogen atoms were refined anisotropically, and hydrogen atoms were placed in calculated idealized positions. The residual peak and hole electron densities were and e Å -3, respectively. The absorption coefficient was mm -1. The least squares refinement converged normally with residuals of R(F) = , wr(f2) = and a Goodness-of-fit on F² = [I>2σ(I)]. C 20 H 24 ClN 3 Ni, Mw = , crystal size 0.32 x 0.22 x 0.18 mm 3, space group P , Orthorhombic, a = (15) Å, b = (18) Å, c = (3) Å, α = 90, β = 90, γ = 90, V = (5) Å 3, Z = 4, ρ calcd = Mg m -3. Table S1. Selected bond lengths and angles for 3 Bond Length (Å) Angle ( ) Ni1-Cl (4) N1-Ni1-N (6) Ni1-N (13) N2-Ni1-N (6) Ni1-N (14) N3-Ni1-Cl (4) Ni1-N (14) N1-Ni1-Cl (4) N3-C (2) C1-N1-C (12) N3-C (2) C17-N3-C (12) N1-C (2) Ni1-N3-C (9) N1-C (2) Ni1-N3-C (10) Crystallographic details for [( Aze N Me NN)NiCl] (4) A total of reflections (-13 h 13, -11 k 7, -38 l 36) were collected at T = 140(2) K of which 6114 were unique [R(int) = ]; Cu Kα radiation (λ= Å). The structure was solved by the direct methods. All non-hydrogen atoms were refined anisotropically, and hydrogen atoms were placed in calculated idealized positions. The residual peak and hole electron densities were and e Å -3, respectively. The absorption coefficient was S2

3 3.295 mm -1. The least squares refinement converged normally with residuals of R(F) = , wr(f2) = and a Goodness-of-fit on F² = [I>2σ(I)]. C 17 H 20 ClN 3 Ni, Mw = , crystal size 0.36 x 0.32 x 0.18 mm 3, space group Pna2 1, Orthorhombic, a = (2) Å, b = (3) Å, c = (10) Å, α = 90, β = 90, γ = 90, V = (15) Å 3, Z = 8, ρ calcd = Mg m -3. Table S2. Selected bond lengths and angles for 4 Bond Length (Å) Angle ( ) Ni1-Cl (13) N2-Ni1-N (18) Ni1-N (4) N2-Ni1-N (18) Ni1-N (4) N3-Ni1-Cl (13) Ni1-N (4) N1-Ni1-Cl (12) N3-C (6) C1-N1-C (4) N3-C (6) C15-N3-C (4) N1-C (6) Ni1-N3-C (3) N1-C (6) Ni1-N3-C (3) Crystallographic details for [( Morph N Me NN)NiCl] (5) A total of reflections (-28 h 25, -11 k 11, -15 l 21) were collected at T = 140(2) K of which 6743 were unique [R(int) = ]; Cu Kα radiation (λ= Å). The structure was solved by the direct methods. All non-hydrogen atoms were refined anisotropically, and hydrogen atoms were placed in calculated idealized positions. The residual peak and hole electron densities were and e Å -3, respectively. The absorption coefficient was mm -1. The least squares refinement converged normally with residuals of R(F) = , wr(f2) = and a Goodness-of-fit on F² = [I>2σ(I)]. C 18 H 22 ClN 3 NiO, Mw = , crystal size 0.41 x 0.35 x 0.24 mm 3, space group P2 1 /c, Monoclinic, a = (5) Å, b = (13) Å, c = (3) Å, α = 90, β = (3), γ = 90, V = (11) Å 3, Z = 8, ρ calcd = Mg m -3. Table S3. Selected bond lengths and angles for 5i Bond Length (Å) Angle ( ) Ni2-Cl (6) N5-Ni2-N (7) Ni2-N (16) N5-Ni2-N (7) Ni2-N (18) N6-Ni2-Cl (5) Ni2-N (17) N4-Ni2-Cl (5) N6-C (2) C19-N4-C (18) N6-C (2) C33-N6-C (14) N4-C (3) Ni2-N6-C (12) N4-C (3) Ni2-N6-C (12) S3

4 Table S4. Selected bond lengths and angles for 5j Bond Length (Å) Angle ( ) Ni1-Cl (6) N2-Ni1-N (7) Ni1-N (16) N2-Ni1-N (7) Ni1-N (17) N3-Ni1-Cl (5) Ni1-N (17) N1-Ni1-Cl (5) N3-C (2) C1-N1-C (18) N3-C (2) C15-N3-C (14) N1-C (3) Ni1-N3-C (11) N1-C (3) Ni1-N3-C (12) Crystallographic details for [( Pip N Me NN)NiCl] (6) A total of reflections (-9 h 12, -14 k 14, -24 l 22) were collected at T = 140(2) K of which 4335 were unique [R(int) = ]; Mo Kα radiation (λ= Å). The structure was solved by the direct methods. All non-hydrogen atoms were refined anisotropically, and hydrogen atoms were placed in calculated idealized positions. The residual peak and hole electron densities were and e Å -3, respectively. The absorption coefficient was mm -1. The least squares refinement converged normally with residuals of R(F) = , wr(f2) = and a Goodness-of-fit on F² = [I>2σ(I)]. C 19 H 24 ClN 3 Ni, Mw = , crystal size 0.63 x 0.40 x 0.29 mm 3, space group P2 1 /n, Monoclinic, a = (3) Å, b = (3) Å, c = (6) Å, α = 90, β = (3), γ = 90, V = (10) Å 3, Z = 4, ρ calcd = Mg/m 3. Table S5. Selected bond lengths and angles for 6 Bond Length (Å) Angle ( ) Ni1-Cl (5) N2-Ni1-N (6) Ni1-N (13) N2-Ni1-N (6) Ni1-N (13) N3-Ni1-Cl (4) Ni1-N (13) N1-Ni1-Cl (4) N3-C (2) C1-N1-C (13) N3-C (2) C15-N3-C (12) N1-C (2) Ni1-N3-C (9) N1-C (2) Ni1-N3-C (9) S4

5 2. Synthesis of complex 7 H 2 N OH CuCl H TsCl + KOH N TBA. HSO N OH 4 I rt, 16 h NaOH Br toluene Br Br 7a, 83% rt, 1 h 7b, 67% Scheme S1. Synthesis of the Pro-Ligand 7H. NH 2 NMe 2 NH Pd 2(dba)3 dppf, NaOt-Bu NMe 2 toluene 110 C, 16 h 7H, 63% N Synthesis of 2-((2-bromophenyl)amino)ethan-1-ol (7a); according to a published procedure. 1 To CuCl (0.1 equiv, 2.2 mmol, 218 mg) and KOH (2 equiv, 44 mmol, 2.47 g) were added 2-aminoethan-1- ol (3 equiv, 66 mmol, 4.0 ml) and 1-bromo-2-iodobenzene (1 equiv, 22 mmol, 2.83 ml). Reaction mixture was stirred at room temperature for 16 h. It was then diluted with ethylacetate (20 ml), washed with water and brine, dried over anhydrous Na 2 SO 4 and evaporated. The crude product was purified by column chromatography on silica gel (Hexane/EtOAc 5:1) to afford the 2-((2- bromophenyl)amino)ethan-1-ol 7a as amber oil. Yield: 3.95 g (83%). 1 H-NMR (400 MHz, CDCl 3 ): (m, 1H), (m, 1H), (m, 1H), 6.60 (td, J = 7.7, 1.5 Hz, 1H), 4.61 (s, 1H), 3.85 (t, J = 5.3 Hz, 2H), 3.35 (t, J = 5.3 Hz, 2H), 2.03 (d, J = 13.6 Hz, 1H). 13 C-NMR (101 MHz, CDCl 3 ): 145.0, 132.7, 128.6, 118.4, 111.7, 110.3, 61.2, HRMS (ESI) for ([M+H] + : C 8 H 11 BrNO + ), calculated: , found: Synthesis of 1-(2-bromophenyl)aziridine (7b); according to a published procedure. 2 A solution of NaOH 50% (2 ml) was added to a mixture of 2-((2-bromophenyl)amino)ethan-1-ol 7a (17 mmol, 3.67 g), p-toluenesulfonyl chloride (1.2 equiv, 20 mmol, 3.89 g) and tetrabutylammonium hydrogensulfate (0.2 equiv, 3.4 mmol, 1.15 g) in toluene (20 ml). The reaction mixture was then stirred at room temperature for 1 h. Water was added (20 ml), product was extracted with EtOAc (3 20 ml). The organic phase was dried over anhydrous Na 2 SO 4 and evaporated. The crude product was purified by column chromatography on silica gel (Hexane/EtOAc 95:5) to deliver the pure 1-(2- bromophenyl)aziridine 7b. Yield: 2.26 g (67%). 1 H-NMR (400 MHz, CDCl 3 ): 7.37 (dd, J = 7.9, 1.5 Hz, 1H), 7.10 (td, J = 7.8, 1.5 Hz, 1H), (m, 1H), 6.48 (dd, J = 8.2, 1.3 Hz, 1H), 2.38 (s, 4H). 13 C- NMR (101 MHz, CDCl 3 ): 144.0, 132.4, 129.8, 127.6, 118.3, 110.9, HRMS (ESI) for ([M+H] + : C 8 H 9 BrN + ), calculated: , found: S. Naoe, T. Saito, M. Uchiyama, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 2015, 17, K. Sriraghavan, V. T. Ramakrishnan, Synth. Commun. 2001, 31, S5

6 N 1,N 1 -dimethylbenzene-1,2-diamine was prepared according to a literature procedure. 3 Synthesis of N 1 -(2-(aziridin-1-yl)phenyl)-N 2,N 2 -dimethylbenzene-1,2-diamine (7H). It was synthesized in a procedure similar to the one described for 4H except that N 1,N 1 -dimethylbenzene- 1,2-diamine (1.2 equiv, 10 mmol, g) and 1-(2-bromophenyl)aziridine 7b (1 equiv, 8.3 mmol, 1.64 g) were used instead of 2-(azetidin-1-yl)aniline and 2-bromo-N,N-dimethylaniline, respectively. Yield: 1.32 g (63%). 1 H-NMR (400 MHz, CDCl 3 ): (m, 1H), 7.40 (dd, J = 8.0, 1.2 Hz, 1H), 7.22 (dd, J = 7.8, 1.3 Hz, 1H), (m, 3H), (m, 1H), (m, 2H), 2.79 (s, 6H), 2.18 (s, 4H). 13 C- NMR (101 MHz, CDCl 3 ): 143.6, 143.0, 137.9, 136.6, 124.0, 123.0, 120.5, 120.0, 119.9, 119.7, 116.5, 114.9, 44.2, HRMS (ESI) for ([M+H] + : C 16 H 20 N + 3 ), calculated: , found: NH N NMe 2 1) n -BuLi THF, rt, 4 h 2) NiCl 2.dme THF, rt, 16 h N N Ni Cl NMe 2 7H 7, 82% Scheme S2. Synthesis of Ni Pincer Complex 7. Synthesis of N 1 -(2-(aziridin-1-yl)phenyl)-N 2,N 2 -dimethylbenzene-1,2-diamine nickel(ii) chloride (7). It was synthesized in a procedure similar to the one described for 3 except that N 1 -(2-(aziridin-1- yl)phenyl)-n 2,N 2 -dimethylbenzene-1,2-diamine 7H (659 mg, 2.6 mmol) was used instead of bis(2- (pyrrolidin-1-yl)phenyl)amine. Yield: 739 mg (82%). No crystals suitable for X-ray analysis could be afforded. 1 H-NMR (400 MHz, CDCl 3 ): (m, 1H), 7.19 (d, J = 7.5 Hz, 2H), (m, 3H), (m, 2H), 2.92 (s, 6H), (m, 2H), (m, 2H). 13 C-NMR (101 MHz, CDCl 3 ): 146.8, 145.0, 129.1, 128.3, 127.2, 125.4, 120.2, 116.0, 116.0, 115.3, 114.2, 113.5, 70.2, P. Ren, O. Vechorkin, Z. Csok, I. Salihu, R. Scopelliti, X. L. Hu, Dalton Trans. 2011, 40, S6

7 3. "Pseudo bite angle" Figure S1. "Pseudo bite angle" of complexes 1-6 S7

8 4. Stability Experiments for Suzuki-Miyaura Coupling Following the general procedure used for the alkyl-alkyl Suzuki-Miyaura reactions, the reaction mixtures were stirred at room temperature during a pre-stirring time before the simultaneous addition of the (4-iodobutyl)benzene and the 9-octyl-9-borabicyclo[3.3.1]nonane (n-octyl-(9-bbn)). Reaction mixture were then stirred for 24 h at room temperature (Table S1). Table S6. Stability Experiments for Suzuki Coupling with a Pre-Stirring Time of 10 min Cat (5 mol %) a) 1.6 equiv NaOH 0.5 equiv NaI 2 equiv i-proh 1,4-dioxane, rt, 10 min b) PhBuI (0.2 mmol) 1.6 equiv n -Octyl-(9-BBN) rt, 24 h n-octyl Entry Pre-stirring Conv. Yield H-Product Cat. Time (%) (%) (%) Elim. (%) < min 4 3 < < 5 0 nd a nd 8 2 < 5 0 nd nd 9 3 < 5 0 nd nd 4 h 10 4 < 5 0 nd nd 11 5 < 5 0 nd nd 12 6 < 5 0 nd nd a nd = non determinate S8

9 5. Inhibition Studies for Kumada Coupling Following the general procedure used for the alkyl-alkyl Kumada reactions, the inhibition experiments were conducted with 1 mol % of catalyst (0.002 mmol) and 10 mol % of extra ligand (10 equivalent relative to catalyst, 0.02 mmol) in the starting reaction mixture. Amount of 10 mol % of extra ligand were: 2.3 µl of 2,4-lutidine, 1.6 µl of pyridine and 5.2 mg of PPh 3. Table S7. Conversion and Product Distribution for the Kumada Coupling of (3-Iodobutyl)benzene with n-octylmgcl in presence of 10 mol % of exogenous ligand I + n-octyl MgCl cat (1 mol %) Ligand (10 mol %) DMA/THF, -20 C, 2 h n-octyl Entry cat Ligand Conv. Yield R-H Elim. R-R R-Cl (%) (%) (%) (%) (%) (%) ,4-Lutidine Pyridine PPh ,4-Lutidine Pyridine PPh ,4-Lutidine Pyridine PPh ,4-Lutidine Pyridine PPh ,4-Lutidine Pyridine PPh S9

10 1 H and 13 C NMR Spectra of 1-(2-nitrophenyl)pyrrolidine 3a S10

11 1 H and 13 C NMR Spectra of 1-(2-nitrophenyl)azetidine 4a S11

12 1 H and 13 C NMR Spectra of 4-(2-nitrophenyl)morpholine 5a S12

13 1 H and 13 C NMR Spectra of 1-(2-nitrophenyl)piperidine 6a S13

14 1 H and 13 C NMR Spectra of 2-(pyrrolidin-1-yl)aniline 3b S14

15 1 H and 13 C NMR Spectra of 2-(azetidin-1-yl)aniline 4b S15

16 1 H and 13 C NMR Spectra of 2-morpholinoaniline 5b S16

17 1 H and 13 C NMR Spectra of 2-(piperidin-1-yl)aniline 6b S17

18 1 H and 13 C NMR Spectra of 1-(2-bromophenyl)pyrrolidine 3c S18

19 1 H and 13 C NMR Spectra of 2-((2-bromophenyl)amino)ethan-1-ol 7a S19

20 1 H and 13 C NMR Spectra of 1-(2-bromophenyl)aziridine 7b S20

21 1 H and 13 C NMR Spectra of bis(2-(pyrrolidin-1-yl)phenyl)amine 3H S21

22 1 H and 13 C NMR Spectra of N 1 -(2-(azetidin-1-yl)phenyl)-N 2,N 2 -dimethylbenzene-1,2-diamine 4H S22

23 1 H and 13 C NMR Spectra of N 1,N 1 -dimethyl-n 2 -(2-morpholinophenyl)benzene-1,2-diamine 5H S23

24 1 H and 13 C NMR Spectra of N 1,N 1 -dimethyl-n 2 -(2-(piperidin-1-yl)phenyl)benzene-1,2-diamine 6H S24

25 1 H and 13 C NMR Spectra of N 1 -(2-(aziridin-1-yl)phenyl)-N 2,N 2 -dimethylbenzene-1,2-diamine 7H S25

26 1 H and 13 C NMR Spectra of bis(2-(pyrrolidin-1-yl)phenyl)amine nickel(ii) chloride 3 S26

27 1 H and 13 C NMR Spectra of N 1 -(2-(azetidin-1-yl)phenyl)-N 2,N 2 -dimethylbenzene-1,2-diamine nickel(ii) chloride 4 S27

28 1 H and 13 C NMR Spectra of N 1,N 1 -dimethyl-n 2 -(2-morpholinophenyl)benzene-1,2-diamine nickel(ii) chloride 5 S28

29 1 H and 13 C NMR Spectra of N 1,N 1 -dimethyl-n 2 -(2-(piperidin-1-yl)phenyl)benzene-1,2-diamine nickel(ii) chloride 6 S29

30 1 H and 13 C NMR Spectra of N 1 -(2-(aziridin-1-yl)phenyl)-N 2,N 2 -dimethylbenzene-1,2-diamine nickel(ii) chloride 7 S30

31 1 H and 13 C NMR Spectra of [( Me N 2 N)Ni(NCCH 3 )]BF 4 8 S31

32 1 H and 13 C NMR Spectra of [( Pyr N Me NN)Ni(NCCH 3 )]BF 4 9 S32

33 1 H and 13 C NMR Spectra of [( Pyr N 2 N)Ni(NCCH 3 )]BF 4 10 S33

34 1 H and 13 C NMR Spectra of [( Aze N Me NN)Ni(NCCH 3 )]BF 4 11 S34

35 1 H and 13 C NMR Spectra of [( Morph N Me NN)Ni(NCCH 3 )]BF 4 12 S35

36 1 H and 13 C NMR Spectra of [( Pip N Me NN)Ni(NCCH 3 )]BAr F 13 S36

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