Table 1. Selected optimization studies a .
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Entry | Ligand (12 mol%) | Solvent | Bite angle b (°) | Yield c |
1 | dppf | Xylenes | 96 | 24% (34%) |
2 | dppm | Xylenes | 72 | <5% |
3 | dppe | Xylenes | 85 | <5% |
4 | dppp | Xylenes | 91 | 13% |
5 | dppb | Xylenes | 98 | 29% |
6 | DPEphos | Xylenes | 104 | 11% |
7 | t-BuXphos | Xylenes | — | 43% |
8 | Xantphos | Xylenes | 111 | 85% |
9 | Xantphos | m-Xylene | 111 | 63% (71%) |
10 | Xantphos | o-Xylene | 111 | 29% (35%) |
11 | Xantphos | p-Xylene | 111 | 62% |
12 | Xantphos | Ethylbenzene | 111 | 91% |
aConditions: ynone 1a (0.20 mmol), [Rh] : ligand = 1 : 1.2, solvent (0.1 M).
bSee ref. 12 for bite-angle values.
cIsolated yields; number in parenthesis is percent conversion of starting material.