Synthesis of substituted dihydrobenzofurans via tandem S(N)Ar/5-exo-trig cyclization.

A tandem SNAr/5-exo-trig cyclization reaction is reported that converts N-alkyl- and -arylimines derived from o-fluorobenzaldehydes into 3-amino-2,3-dihydro-2,2-diarylbenzofurans in moderate to good yields. Diarylmethoxide coupling partners serve the dual role of nucleophile in the SNAr step and catalytic base in the cyclization step. With a subset of the substrates, a further base-induced elimination of the 3-amino-2,3-dihydro-2,2-diarylbenzofuran to a phenolic enamine was observed.