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. 2019 Mar 8;4(3):5064–5075. doi: 10.1021/acsomega.9b00315

Table 1. Optimization of the One-Pot RCM/Oxidation/1,3-Dipolar Cycloaddition Protocol.

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    RCM
1,3-dipolar cycloaddition
isolated yield
entry Grubbs II (mol %) solvent temp. (°C) conc. (M) time (min) temp. (°C) conc. (M) time (min) (%, two steps)
1 10 benzene reflux 0.01 30 reflux 0.01 60 15
2 20 benzene reflux 0.01 30 reflux 0.01 60 11
3 5 benzene reflux 0.01 30 reflux 0.01 60 16
4 1 benzene reflux 0.01 30 reflux 0.01 60 18
5 1 toluene 80 0.01 30 80 0.01 60 18
6 1 toluene 80 0.01 10 80 0.01 30 18
7a 1 toluene 80 0.1 10 80 0.1 30 5
8b 1 toluene 80 0.01 10 80 0.01 30 15
a

Cross metathesis product was also isolated in 28% yield.

b

Reaction was performed in a glovebox.