Table 1. Optimization of the Tandem NCR Cyclizationa.
temp (°C) | solvent | addition time (h) | % yield (isolated) |
---|---|---|---|
80 | Ph-Me | 0 | 40–50 |
21 (sunlamp) | Ph-Me | 0 | 17 |
80 | Ph-CF3 | 0 | 27 |
80 | Ph-Me | 1 | 61 (+Cl· transfer pdt.) |
80 | Ph-H | 1 | 21 |
110 | Ph–Me | 1 | 74 |
All reactions were performed using 0.5 equiv of AIBN, 2 equiv of Bu3SnH, at 0.01 M. Addition over 1 h indicates a solution of AIBN and Bu3SnH was added dropwise over 1 h to a heated solution of the substrate in the indicated solvent.