Add time:07/29/2019         Source:sciencedirect.com

Tetrafluoroindole (5), a precursor for potential biologically-active compounds, was prepared previously in a four-step synthesis from C6F6. However, catalytic reduction of pentafluorophenylacetonitrile (2) to 2-pentafluorophenylethyl amine (3) is accompanied by a significant amount of a secondary amine, which, like 3, undergoes cyclization to an indoline and subsequent dehydrogenation to a new indole 8. The side-reaction in the reduction of 2 to 3 is obviated by the use of LiAlH4AlCl3 (1:1). The final aromatization to yield 5 is vastly improved by replacing MnO2 with DDQ.

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