α-Functionalization of Tetrahydroisoquinolines with Activated Alkyl Bromide under Photoredox Catalysis

Abstract

Table of Contents 1.General 2. α-Functionalization of tetrahydroisoquinolines 3. NMR spectra 1.General 1 H, 19 F NMR spectra were measured on a JEOL JNM-ECA-500 spectrometer at 500 and 470 MHz, respectively. 13C NMR spectra were recorded on a JEOL JNM-ECA-500 spectrometer at 125 MHz.Chemical shifts were reported downfield from TMS (d = 0 ppm), CDCl 3 or CD 3 CN for 1 H NMR. For 13 C NMR, chemical shifts were reported in a scale relative to CDCl 3 or CD 3 CN.For 19 F NMR, chemical shifts were reported in a scale relative to a CFCl 3 external standard (d = 0 ppm).Infrared spectra were measured on a SHIMADZU IRPrestige-21 and only diagnostic absorptions are listed.ESI-MS data were taken on a Thermo SCIENTIFIC ACCELA Exactive liquid chromatography mass spectrometer.Column chromatography was performed with silica gel N-60 (40-100 mol purchased from Kanto Chemical Co., Inc.TLC analysis was performed on Silica gel 60 F 254 -coated glass plates (Merck).Visualization of TLC plates was carried out by means of ultraviolet (UV) irradiation at 254 nm and/or by spraying 12-molybdo(VI)phosphoric acid ethanol solution as the developing agent.Dehydrated N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), and dichloromethane (CH 2 Cl 2 ) were purchased from Wako Pure Chemical Industries, Ltd.Dehydrated acetonitrile (MeCN) was purchased from Sigma-Aldrich Co. LLC.Other reagents were purified by usual methods.Tetrahydroisoquinolines were prepared according to literature procedures. [1