Published April 17, 2015
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Journal Article
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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.
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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ol5b00743_si_001.pdf
Additional details
- Eprint ID
- 56587
- DOI
- 10.1021/acs.orglett.5b00743
- Resolver ID
- CaltechAUTHORS:20150413-091100878
- N00014-12-1-0596
- Office of Naval Research (ONR)
- Deutscher Akademischer Austauschdienst (DAAD)
- F32GM108145
- NIH Postdoctoral Fellowship
- CHE-0639094
- NSF
- Created
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2015-04-13Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field