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Published April 17, 2015 | Supplemental Material
Journal Article Open

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


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.

Additional Information

© 2015 American Chemical Society. Received: March 13, 2015. Publication Date (Web): April 8, 2015. The research described in this paper was supported financially by the ONR (Award No. N00014-12-1-0596), the DAAD (RISE Worldwide Fellowship to M.K.), and the NIH NIGMS (Award No. F32GM108145; postdoctoral fellowship to K.M.E.). Zachary K. Wickens (Grubbs laboratory, Caltech), Dr. Hans Renata (Arnold laboratory, Caltech), and Dr. Will R. Gutekunst (Hawker laboratory, UCSB) are acknowledged for helpful discussions. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology (CHE-0639094).

Attached Files

Supplemental Material - ol5b00743_si_001.pdf

Supplemental Material - ol5b00743_si_002.cif

Supplemental Material - ol5b00743_si_003.cif

Supplemental Material - ol5b00743_si_004.cif


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