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30th January 2018 @ 14:22

Another experiment was set up in attempt to highlight if it was the electronic configuration of the starting material that was preventing succesful reaction. Efforts were made to replicate the same conditions as the other experiments but Bromobenzene was used in stead of SBM005.

Reaction Scheme

Bromobenzene (20mg) was added in degassed toluene (2ml). Morpholine (15ul) was added, followed by Spanphos (approx. 1mg), NaOtBu (16.38mg) and Pd(DBA)3 (approx. 0.6mg) and left stirring at 80-1000C. This was repeated with the same conditions but changing the ligand to DPPF, then JohnPhos, then BINAP.

TLCs (5% methanol, 95% DCM) were run at 1 day and 14 days. 

TLC BB Binap

At 14 days, the DPPF Reaction mixture was extracted with HCl (2ml) and EtOAc (3x3ml) and then dried with MgSO4 before being put under rotary evap.

NMR of crude products showed experiments were unsuccessful.