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The publication describes a new three-component reaction allowing the synthesis of α,β-unsaturated esters substituted with fluoroalkyl groups directly from alkynes, fluoroalkyl iodides and aryl formates. An important part of the work is devoted to in-depth mechanistic investigations revealing that the tandem process is composed of radical iodoperfluoroalkylation involving Pd(0)/Pd(I) chemistry and subsequent aryloxycarbonylation proceeding through Pd(0)/Pd(II) catalytic cycle employing carbon monoxide and phenoxide formed through off-cycle, base-induced decomposition of aryl formate. The developed conditions allow the reaction to be carried out without an external source of toxic carbon monoxide.
The research was carried out within the OPUS 11 grant from the National Science Center (2016/21/B/ST5/03178) using resources provided by Wroclaw Centre for Networking and Supercomputing (grant no. 518).