Carbon Dioxide → Phenylpropiolic Acid
Reaction equation
[C:1](=[O:3])=[O:2].[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)#[CH:5]>>[C:6]1([C:4]#[C:5][C:1]([OH:3])=[O:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
The longer reaction time for the P1 catalysed reaction may be due to the heterogeneous reaction behavior in this solid catalyst system. A reaction intermediate Poly(NHC—CO2)0.5(NHC—Cu)0.5 was synthesized by reaction of Poly(NHC)0.5(NHC—Cu)0.5 (P1) with CO2. This intermediate was directly used to react with stoichiometric amount 1-ethynylbenzene (1 eq. to NHC—CO2) under standard condition without an additional CO2 source. 52% yield of phenylpropiolic acid was obtained in 24 hours. With these experiment results, it is believe that the unique structure of P1 catalyst is the key to the high activities. The free carbene species in the structure are randomly located around copper center and act as an organo catalyst to activate CO2. This essential step may reduce the activation energy barrier for CO2 insertion.
Workup
- customThe longer reaction time for the P1
- customreaction
- custom5 was synthesized by reaction of Poly(NHC)0
Sources & evidence
- ORD record
- ord-83714cfe154c4cc88941d62e5c8a5872
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816127B2
Reaction notes
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