1: 1-methyl-1H-indole; chlorocatecholborane With AlCl3, aluminium chloride; triethylamine in dichloromethane T=20°C; 6 h; Inert atmosphere; 2: 2,3-dimethylbutane-2,3-diol With triethylamine in dichloromethane Irradiation;

1: 1-methyl-1H-indole With 2,6-dimethylpyridine; AlCl3, aluminium chloride; boron trichloride in n-heptane; dichloromethane T=20°C; 14 h; Inert atmosphere; 2: 2,3-dimethylbutane-2,3-diol With triethylamine in n-heptane; dichloromethane T=20°C; 0.5 h; Irradiation;

Et3N in dichloromethane byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excess Et3N added; pinacol added; stirred for 4 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;

AlCl3; 2,6-lutidine in dichloromethane 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 14 h;

C32H12BF24(1-)*C42H38F3PRuS(1+) T=80°C; 24 h; GloveboxSealed tubeInert atmosphere; SolventReagent/catalyst;

triethylamine in dichloromethane T=20°C; 1.25 h; Inert atmosphere;

1.1: AlCl3, aluminium chloride; triethylamine / dichloromethane / 20 °C / Inert atmosphere 1.2: 4 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 1 h / Inert atmosphere View Scheme

C22H34CoN3 in neat (no solvent) T=80°C; 24 h; Inert atmosphereGlovebox;

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere; |Schlenk technique 1.2: 20 °C 2.1: C32H12BF24(1-)*C42H38F3PRuS(1+) / 24 h / 80 °C / |Glovebox; |Sealed tube; |Inert atmosphere View Scheme

in dichloromethane; dichloromethane-d2 using standard Schlenk techniques; Et3N in CD2Cl2-CH2Cl2 treated with B compd. and AlCl3; treated with N-methylindole for 3 h; treated with Et3Nand pinacol; rotated for 30 min; solvent removed under vac.; dried for 1 h; hexane added; filtered; hexane removed from filtrate under vac.; dried overnight; monitored by (1)H and (11)B NMR spectra;