anie_200900212_sm_miscellaneous_information.pdf

Supporting Information ? Wiley-VCH 2009 69451 Weinheim, Germany S 1 A Novel Multicomponent Reaction of Arynes, Isocyanides, and Terminal Alkynes: Highly Chemo- and Regioselective Synthesis of Polysubstituted Pyridines and Isoquinolines Feng Shaa, Xian Huang* a, b a. Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou 310028, P. R. China b. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China huangx@mail.hz.zj.cn Supporting Information List of contents Experiment procedures……………………………………….……S2-S4 Characterization data: 4a-b and 6a-l…………………………………………………….S5-S9 5a-f and 5g-i……………………………………………………S10-S13 1H NMR and 13C NMR spectra………………………………….S14-S37 2D 1H-1H NOESY spectra………………………………………S38-S46 S 2 1. Experiment procedures All reactions were performed under a purified N2 atmosphere. Dry solvents were distilled prior to use: THF, Et2O, and toluene were distilled from sodium-benzophenone; MeCN were distilled from P2O5; CH2Cl2 was distilled from CaH2. Petroleum ether refers to the fraction with boiling point in the range 60 – 90 °C. All 1H NMR and 13C NMR spectra were measured in CDCl3 with TMS as the internal standard. Chemical shifts are expressed in ppm and J values are given in Hz. Melting points are uncorrected. 2-(Trimethylsilyl)aryl triflates 1 were prepared according to the known methods.1 General Procedure 1.1.1 Multicomponent reaction of 2-(trimethylsilyl)aryl triflates 1, isocyanides 2, and terminal alkynes 3 leading to polysubstituted pyridines 6a-k To a stirred solution of 2-(trimethylsilyl)aryl triflate 1 (0.65 mmol), isocyanide 2 (0.5 mmol), and terminal alkyne 3 (1.5 mmol) in dry MeCN (0.5 mL) and dry toluene (2 mL), CsF (1.3 mmol, 198 mg) was added under nitrogen atmosphere. The reaction mixture was then allowed to stir at 75 o