Optimization of the reaction conditions.
| ||
|---|---|---|
| Entry | Deviation | Yieldb |
| 1 | Nonea | 88% |
| 2 | No carboxylic acid | 24% |
| 3 | pTsOH instead of undec. acid | 8% |
| 4 | Sodium laurate instead of undec. acid | 47% |
| 5 | 1.1 eq. thiophene | 92% |
| 6 | Pd2(dba)3 | 8% |
| 7 | No Pd(OAc)2 | — |
| 8 | No AgOAc | — |
| 9 | Solvent free in 10 eq. undec. acid | — |
| 10 | EtOH as solvent, no PS-750-M | 55% |
| 11 | 2 wt%/1 wt% PS-750-M in H2O | 87%/86% |
| 12 | 2 wt% TPGS-750-M/SPGS-550-M in H2O | 81%/86% |
a
Standard reaction conditions; aryl iodide (1.5 eq.), Pd(OAc)2 (10 mol%), AgOAc (1.0 eq.), undecanoic acid (1.0 eq.), PS-750-M (3 wt% in H2O), 16 h, rt.
b
Yield determined by 1H NMR using an internal standard.