29576-13-4Relevant articles and documents
New insights into the alkoxycarbonylation of propargyl alcohol
Scrivanti,Beghetto,Bertoldini
, p. 38 - 42 (2017/11/15)
The challenging carbonylation of propargyl alcohol is effectively catalyzed by Pd(OAc)2 in combination with diphenyl-(6-methyl-pyridin-2-yl)phosphine and methanesulfonic acid. In dichloroethane at 20–50 °C, the reaction affords with almost complete regioselectivity alkyl 2-(hydroxymethyl)acrylates. Turnover frequency numbers (TOF) of up to 450 h?1 can be achieved working at 50 °C, while a maximum turnover number (TON) of about 730 is obtained at 30 °C. The catalyst longevity is limited because the carbonylation product reacts with the phosphorus atom of the ligand to give a quaternary phosphonium salt. This reaction leads to deactivation of the catalyst and eventually to palladium black formation.