Table 2.
1,6-Enyne 1a | 5,6-Bicyclohexadiene 2 | ||||
---|---|---|---|---|---|
Entry | X = | Y/Y = | Yield (%)b | ||
1 | TsN | a | CO2Me | a | 92 |
2 | ” | ” | COPh | b | 84 |
3 | ” | ” | CONMe2 | c | 61 |
4 | C(CO2Me)2 | b | CO2Me | d | 85 |
5 | ” | ” | COPh | e | 74 |
6 | ” | ” | CONMe2 | f | 54 |
7 | O | c | CO2Me | g | 84 |
8 | ” | ” | COPh | h | 81 |
9 | ” | ” | CONMe2 | i | 55 |
All reactions were carried out on a 0.25 mmol reaction scale utilizing 10 mol% of Wilkinson's catalyst [RhCl(PPh3)3] modified with 20 mol% of silver triflate with the requisite 1,2-disubstituted alkyne (3 equiv.) under an atmosphere of argon.9
Isolated yield.