Skip to main content
. Author manuscript; available in PMC: 2008 Oct 31.
Published in final edited form as: J Am Chem Soc. 2007 Oct 5;129(43):12948–12949. doi: 10.1021/ja0762240

Table 1.

Dependence on Solvent and Liganda

graphic file with name nihms64159f5.jpg
entry R solvent ligand (equiv) yield (%) 2 yield (%) 7
1 EH PhCH3 -- <5 trace
2 EH PhCF3 -- 7 trace
3 EH PhCH3 8 (0.2) 41 7
4 EH PhCH3 8 (0.8) 63 17
5 EH PhCF3 8 (0.8) 75 <5
6 OTf PhCF3 8 (0.8) 29 <5
7 OTf PhCH3 9 (0.2) 59 12
8 OTf PhCF3 9 (0.2) 60 <5
a

Reaction conditions: Substrate 1a was dissolved in solvent (0.1 M) and treated with K2CO3 (1 equiv), MnO2 (3 equiv), CuR2 (0.2 equiv) and the specified amount of ligand and stirred in a sealed tube at 120 °C for 24 h.

b

Yields refer to amount of compound isolated after chromatography on SiO2. Remainder of material was always unreacted starting 1a. EH = 2-ethylhexanoate.