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1 Supplementary Materials for Catalytic borylation of methane Kyle T. Smith, Simon Berritt, Mariano González-Moreiras, Seihwan Ahn, Milton R. Smith III,* Mu-Hyun Baik,* Daniel J. Mindiola* *Corresponding author. (M.R.S.); (M.-H.B.); (D.J.M.) This PDF file includes: Materials and Methods Supplementary Text Figs. S1 to S15 Tables S1 to S8 References Published 25 March 2016, Science 351, 1424 (2016) DOI: /science.aad9730
2 Table of Contents Materials and Methods...S3-S39 Experimental S40-S51 Figures S7-S15.S52-S60 References S61-S62 S2
3 Materials and Methods All reagents were used as purchased from commercial suppliers. Solvents were purchased from Sigma Aldrich in anhydrous, sure-seal quality, and used with no further purification. 2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane (H 3 CBpin) and 2,2'- methylenebis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane (H 2 C(Bpin) 2 ) were purchased from Sigma Aldrich and TCI Chemicals, respectively, and used as received. The dimeric iridium precatalysts, ligands, and boron sources were purchased from commercial sources and stored in the glovebox. (MesH)Ir(Bpin) 3 was synthesized via previously reported methods (32). The synthesis of the 3,8-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1,10-phenanthroline ligand (L4) is outlined below. A 99 atom% 13 C-labled methane cylinder was purchased from Sigma Aldrich and used in labeling studies with no further purification. Synthesis of 3,8-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline In the glovebox, a 500 ml Schlenk flask was charged with [Ir(COD)(μ-OMe)] 2 (66.4 mg, 0.1 mmol, 0.5 mol %) in THF (50 ml). B 2 pin 2 (7.6 g, 30 mmol) was dissolved in THF (100 ml), added to the solution, and stirred for 5 minutes. Then, 1,10-phenanthroline (3.6 g, 20 mmol) was added as a solution in THF (100 ml). The Schlenk flask was sealed with a septum, and brought out of the glovebox. The septum was replaced with a reflux condenser under N 2, and the reaction was heated to reflux at 85 C for 4.5 hours. The volatiles were removed under vacuum, to afford the crude product. Dry heptane (35 ml) was added, and the mixture was heated to 85 C and stirred until a fine powder was observed in the flask (approximately 1 h). The solution was filtered hot, the solid was washed with hot heptane (10 ml), and the solid dried under vacuum to afford the product as a tan powder (6.52 g, 15.1 mmol, 76%). mp = 260 C (dec). 1 H NMR (CDCl 3, 500 MHz) δ 1.39 (s, 24H), 7.77 (s, 2H), 8.65 (d, 2H, J=1.5 Hz), 9.45 (d, 2H, J=1.4 Hz); 13 C NMR (CDCl 3, 125 MHz) δ 24.8, 84.3, 126.5, 128.3, 143.4, 147.5, 154.9; 11 B NMR (CDCl 3, MHz) δ 30.9; HRMS (ESI) m/z Calcd for C 24 H 31 B 2 N 2 O 4 [M+H] , found S3
4 Fig. S1 1 H NMR (CDCl 3, 500 MHz) S4
5 Fig. S2 13 C NMR (CDCl 3, 125 MHz) S5
6 General Experimental High Throughput Experimentation (HTE) was carried out in a Vacuum Atmospheres glovebox operating under a N 2 atmosphere (oxygen typically <5 ppm). The experimental design was accomplished using a Freeslate Library Studio. Screening reactions were carried out in 1 ml vials (30 mm height x 8 mm diameter) in a Freeslate 96-well plate High-pressure (HiP) aluminum reactor block (part # S ) encased by a custom manufactured high pressure clam-shell reactor block attached to a highpressure manifold via a quick connect set-up. A typical reactor in shown in Fig. S3. Liquid chemicals were dosed using multi-channel or single-channel pipettors. Undesired additional solvent was removed using a GeneVac system located inside the glovebox. The reactions were heated and stirred on a New Brunswick Innova 2000 shaker equipped with heating apparatus. Each reaction was agitated using 3mm diameter glass balls. Directly above the glass vial reactor tops was a Teflon barrier sheet, followed by a mm thick silicon-rubber gasket. The reactor plate was then sealed and placed into the enclosed clam-shell reactor. 1 H and 13 C{1H}NMR spectra were recorded on an Agilent DDR2 500 MHz NMR spectrometer equipped with 7600AS 96 sample autosamplers running VnmrJ 3.2A. 1 H, 13 C{ 1 H} chemical shifts are reported referenced to the internal residual proton or carbon resonances of CDCl 3 (δ = ppm or 77.0 ppm). GC/MS analysis was conducted on an Agilent GC/MS, model 6890N coupled with 5973N MSD (mass selective detector) in EI pos mode, and equipped with Agilent 7683 autosampler, and using an HP 5 MS column (30.0 m x µm x 0.25 µm). Helium as carrier gas was maintained at 1.2ml/min. GC method used an initial temperature of 50 C for an initial time of 1.00 minute, with a ramp of 20 C per min over mins, with a final temperature of 250 C. S6
7 Fig. S3 96 well HiP reactor showing 1 ml vials & High Pressure Reactor Shell. S7
8 Computational Details All calculation results was obtained using density functional theory calculations as implemented in the Jaguar 8.9 (33) program. The geometry optimizations were performed with M06 (34) functional and 6-31G** basis set. Iridium was represented using the Los Alamos LACVP basis set, (35-37) which contains effective core potentials. We carried out the single-point calculations of the optimized structures using cc-pvtz(- f) (38) basis set. For iridium, a modified version of LACVP denoted LACV3P was used. Vibrational frequency calculations were performed at the same level of theory as the geometry optimization calculations. Zero-point vibrational energy and entropy corrections were obtained using standard approximations. Solvation energies were obtained from Self-Consistent Reaction field (SCRF) (39-41) calculations with the dielectric constant ε = 7.6 (THF) using the optimized gas phase structures. Transition states were located using the quadratic synchronous transit search methods (QST). (42) The Gibbs free energy in solution phase was computed as follows (43): G(Sol) = G(gas) + G solv (1) G(gas) = H(gas) TS(gas) (2) H(gas) = E(SCF) + ZPE (3) ΔG(Sol) = ΣG(Sol) for products ΣG(Sol) for reactants (4) Fig. S4 Energy diagram of 1,10-phenanthroline (phen) system including enthalpies and free energies. S8
9 Table S1. Cartesian coordinates of the intermediates and transition states of the catalytic cycle. =============================== a =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H H H C H S9
10 H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H H H S10
11 =============================== b =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H H H C H H H S11
12 B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H C H H H S12
13 H H H =============================== b-ts =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H H H C H S13
14 H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H C H S14
15 H H H H H =============================== c =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H H H S15
16 C H H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H S16
17 C H H H H H H =============================== c-isomer =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H S17
18 H H C H H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H S18
19 H H C H H H H H H =============================== c-iso-ts =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H S19
20 C H H H C H H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H S20
21 C H H H C H H H H H H =============================== d =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H S21
22 H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H S22
23 H H C H H H C H H H H H H =============================== e =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C S23
24 C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H H H H B O O C C H H H C C S24
25 H H H C H H H C H H H B O O C C H H H C C H H H C C H H H H H H =============================== e-ts =============================== C Ir C C C C C N C H H S25
26 C C C C N C H H H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H S26
27 H H C H H H H H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C C H S27
28 H H H H H =============================== f =============================== C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H H H S28
29 C H H H B O O C C H H H C C H H H C H H H C H H H H H H B O O C C H H H C C H H H C H H H C S29
30 H H H B O O C C H H H C C H H H C C H H H H H H =============================== f-ts =============================== C Ir C C C C C N C H H C C C C N C H H S30
31 H H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C H H H C H H H H H S31
32 H B O O C C H H H C C H H H C H H H C H H H B O O C C H H H C C H H H C C H H H H H H =============================== g =============================== S32
33 C Ir C C C C C N C H H C C C C N C H H H H B O O C C H H H C C H H H C H H H C H H H B O O C S33
34 C H H H C C H H H C H H H C H H H H H H B O O C C H H H C C H H H C H H H C H H H B O O C C S34
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