Iron-catalysed highly selective hydroalkoxycarbonylation of alkynes using CO as C1 source

T Tewari, R Kumar, SH Chikkali - Catalysis Science & Technology, 2023 - pubs.rsc.org
Catalysis Science & Technology, 2023pubs.rsc.org
Though precious and rare, late-transition metals have been extensively used in metal-
catalysed carbonylation reactions in organic transformations. On the other hand, base
metals are abundant and cheap, but their practical utilization in carbonylation reactions is
rarely explored. Here, we report iron-catalysed hydroalkoxycarbonylation of alkynes to α, β-
unsaturated esters in one pot. A readily available iron precursor [Fe2 (CO) 9] in the presence
of a diimine ligand L7 catalyzes the conversion of alkynes to α, β-unsaturated esters under …
Though precious and rare, late-transition metals have been extensively used in metal-catalysed carbonylation reactions in organic transformations. On the other hand, base metals are abundant and cheap, but their practical utilization in carbonylation reactions is rarely explored. Here, we report iron-catalysed hydroalkoxycarbonylation of alkynes to α,β-unsaturated esters in one pot. A readily available iron precursor [Fe2(CO)9] in the presence of a diimine ligand L7 catalyzes the conversion of alkynes to α,β-unsaturated esters under 10 bar CO pressure. This operationally simple protocol tolerates various functional groups and allows facile access to about 40 α,β-unsaturated esters. The synthetic utility of the reaction has been demonstrated by scaling up the reaction to 1 g and by preparing sunscreen/antifungal agents. The kinetic study suggests that the reaction is an approximate 1st order with respect to the iron catalyst, and the initial rate of the reaction is 3.6 × 10−2 M h−1. Mechanistic investigations using NMR spectroscopy indicated the existence of an [Fe–H] intermediate, and control experiments using a radical trapping reagent and EPR revealed the absence of any radical species in the reaction.
The Royal Society of Chemistry
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