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Synthesis of Substituted Dihydrobenzofurans via Tandem S_NAr/5-Exo-Trig Cyclization

Abstract

A tandem S_NAr/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 S_NAr 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

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