Skip to main content
. Author manuscript; available in PMC: 2015 Oct 6.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Aug 25;53(41):11056–11059. doi: 10.1002/anie.201406393

Table 1.

Optimization of conditions for oxidative [3+2] cycloaddition

graphic file with name nihms637145t1.jpg
Entry[a] Catalyst Oxidant Yield[b]
1 Ru(bpy)3(PF6)2 H2O2 (30% aq) 0%
2 Ru(bpy)3(PF6)2 H2O2•urea 0%
3 Ru(bpy)3(PF6)2 t-BuOOH 0%
4 Ru(bpy)3(PF6)2 m-CPBA 0%
5 Ru(bpy)3(PF6)2 Oxone® 7%
6 Ru(bpy)3(PF6)2 K2S2O8 20%
7 Ru(bpz)3(PF6)2 K2S2O8 75%
8 Ru(bpz)3(PF6)2 Na2S2O8 23%
9 Ru(bpz)3(PF6)2 (NH4)2S2O8 78%
10c Ru(bpz)3(PF6)2 (NH4)2S2O8 0%
11 none (NH4)2S2O8 0%
[a]

All reactions were irradiated for 24 h using 0.10 mmol phenol, 0.13 mmol styrene, 0.20 mmol oxidant, and 0.005 mmol catalyst, unless noted.

[b]

Yields determined by 1H NMR spectroscopy using TMSPh as an internal standard.

[c]

Reaction performed in the dark.