2-(6,6-dimethylcyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of T10.4 (0.750 g, 1.9 mmol) in DMF (4.00 mL, 52 mmol) at 23° C. was added T14.2 (0.92 g, 3.9 mmol), potassium carbonate (0.81 g, 5.8 mmol), and then tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol). The mixture was heated to 90° C. and stirred for 24 hours. The reaction was then cooled to room temperature, diluted with brine, and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield T14.3 as a colorless oil (0.34 g, 48% yield). The reaction was then cooled to room temperature extracted three times with EtOAc After drying over anhydrous magnesium sulfate filtering the organic solvent was removed under reduced pressure the product was then purified on silica gel (0-10% EtOAc in hexanes)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 66.15D (0.750 g, 1.9 mmol) in DMF (4.00 mL, 52 mmol) at 23° C. was added 66.21B (0.92 g, 3.9 mmol), potassium carbonate (0.81 g, 5.8 mmol), and then tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol). The mixture was heated to 90° C. and stirred for 24 hours. The reaction was then cooled to room temperature, diluted with brine, and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 66.21C as a colorless oil (0.34 g, 48% yield). The reaction was then cooled to room temperature extracted three times with EtOAc After drying over anhydrous magnesium sulfate filtering the organic solvent was removed under reduced pressure the product was then purified on silica gel (0-10% EtOAc in hexanes)