Table 1.
Entry | Deviation from standard conditions | 4:5:6:7b | Yield of 4ac |
---|---|---|---|
1 | None | 98:1:0.5:0.5 | 89% (80%) |
2 | (E)/(Z)-1 (1:1.2) | 96:1:1:2 | 83% (75%) |
3 | 45 or 80 °C (dark) | 8:0:0:92 | Trace |
4 | Without PdCl2 | 4:0:0:96 | Trace |
5 | Without AgNTf2 | 91:5:2:2 | 48%d |
6 | Without Cs2CO3 | 62:29:7:2 | 44% |
0.2 mmol scale; (E)-1:2:3 = 1:1.3:1.3.
Determined by GC/MS using pentadecane as internal standard; 4a:4b > 20:1.
Determined by 1H NMR using dibromomethane as internal standard; isolated yields given in parentheses.
Formation of substantial amounts of radical dimerization products was observed.