Killing double bonds softly: the reduction of polymer-bound alkenes

Daniel Fürniss, Ute Schepers, Stefan Bräse
2012 RSC Advances  
General procedures: GP1: Attachment of monoprotected diamines to the resin on the example N-(3-aminopropyl)-2-nitrobenzenesulfonamide 2.00 mmol of the 2-Cl-Trt-Cl resin (4) were swollen in 12 mL dry CH 2 Cl 2 and treated with 6.00 mmol N,N-diisopropylethylamine (DIPEA) and 6.00 mmol N-(3-aminopropyl)-2nitrobenzenesulfonamide. The reaction vessel was closed and shaken for 15 h at room temperature. Afterwards, 3 mL methanol were added and the mixture was shaken for another 15 minutes. The
more » ... inutes. The solvents were removed and the resin was washed with CH 2 Cl 2 /MeOH/CH 2 Cl 2 /MeOH/CH 2 Cl 2 /MeOH/ CH 2 Cl 2 and again CH 2 Cl 2 (3 ×). The resin 5 was dried in vacuo overnight. GP2: Fukuyama-Alkylation and Nosyl-deprotection 0.20 mmol of the resin 5 were swollen in 6 mL N,N-dimethylformamide (DMF) and treated with 1.20 mmol 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1.20 mmol halide. The reaction vessel was closed and shaken for 15 h at room temperature. Afterwards, the solvents were removed and the resin was washed with DMF, CH 2 Cl 2 /MeOH/CH 2 Cl 2 /MeOH/CH 2 Cl 2 and again CH 2 Cl 2 (3 ×). The resin 6 was dried in vacuo overnight. 0.20 mmol of the resin 6 were swollen in 6 mL DMF and treated with 1.00 mmol DBU and 2.00 mmol 2-mercaptoethanol. The reaction vessel was closed and shaken for 1 h at room temperature. Afterwards the solvents were removed and the resin was washed with DMF until the filtrate stayed colorless. The whole procedure was repeated with only 30 minutes of reaction time until the reaction mixture stayed colorless. Afterwards, the resin was washed with DMF, CH 2 Cl 2 /MeOH/CH 2 Cl 2 /MeOH/CH 2 Cl 2 and again CH 2 Cl 2 (3 ×). The resin 8 was dried in vacuo overnight. Electronic Supplementary Material (ESI) for RSC Advances This journal is
doi:10.1039/c2ra22189f fatcat:gfupszbs6nbdppyqdbnw453yqy