反应详情

The starting aryl halide (i.e., (E)-methyl 4-(3-bromobenzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) (0.824 mmol) was dissolved in DMF (8 mL) and H2O (2 mL) was added, forming a suspension. Barium hydroxide (0.213 g, 1.24 mmol) was then added, and the suspension was isolated and back-flushed four times with N2. The boronic acid (i.e. furan-2-boronic acid) (1.23 mmol) was added, and the suspension was isolated and back-flushed with N2 an additional four times and finally sparged with N2 for about 5-10 min. Then tetrakis(triphenylphosphine)palladium(0) (0.143 g, 0.21 mmol) was added, and the reaction was placed in a preheated (80° C.) heating block and stirred for 1 hour. The reaction was diluted with H2O (20 mL) and ethyl acetate (20 mL) and filtered through Celite. The organic layer was collected, washed once with H2O, once with brine, and dried over Na2SO4. Purification by column chromatography afforded the desired coupled product (i.e., (E)-methyl 4-(3-(furan-2-yl)benzylidene)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate). De-protected product (i.e., (E)-methyl 4-(3-(furan-2-yl)benzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) may also be formed.

1. customforming a suspension
2. customthe suspension was isolated
3. customback-flushed four times with N2
4. customthe suspension was isolated
5. customback-flushed with N2 an additional four times
6. customfinally sparged with N2 for about 5-10 min
7. customwas placed in a preheated (80° C.)
8. temperatureheating block
9. filtrationfiltered through Celite
10. customThe organic layer was collected
11. washwashed once with H2O, once with brine
12. dry with materialdried over Na2SO4
13. customPurification by column chromatography
14. customafforded the