Direct Fluoroacylation of Indole with Perfluoroalkyl Iodides

Abstract

Functionalization of perfluoroalkyl compounds has shown huge potential in synthetic chemistry and drug development. Herein, we report a one-pot tandem perfluoroalkylation−defluorination reaction of indole, perfluoroalkyl iodide, and water in the presence of Na 2 S 2 O 4 . A wide array of indole derivatives were efficiently accessed with good yields under mild reaction conditions. The reaction is believed to undergo perfluoroalkylation and follow the defluorination hydrolysis pathway. This study represents an alternative approach for defluorination functionalization.

Silver-Promoted Three-Component Synthesis of Perfluoroalkenyl Pyrroles through Partial Defluorinative Functionalization of Perfluoroalkyl Halides

“…On the basis of our experimental studies and previous reports, − ,− , we proposed a plausible reaction mechanism in Scheme . Initially, a perfluoroalkyl radical A , which is in situ formed through a single-electron transfer (SET) process between reductant and PFAH under silver catalysis, selectively adds to the terminal position of alkyne 1 to deliver a vinyl radical B .…”

“…In addition to classic nucleophilic substitution, direct perfluoroalkylation could be achieved under transition metal catalysis or photocatalysis, which involves the homolysis of the C–X bond in PFAH (Figure A, a) . On the other hand, strategies that exploit a tandem relay of radical perfluoroalkylation and subsequent defluorination provide an appealing means to access perfluoroalkylated acyclic (Figure A, b) or heterocyclic (Figure A, c) compounds . Typically, three carbon–halogen bonds at a single carbon are completely functionalized in one procedure.…”